MiMeDB: Showing metabocard for ouabain (MMDBc0054617)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:21:25 UTC

Update Date

2024-10-11 00:57:23 UTC

Metabolite ID

MMDBc0054617

Metabolite Identification

Common Name

ouabain

Description

Ouabain is only found in individuals that have used or taken this drug. It is a cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like digitalis. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-exchanging ATPase. [PubChem]Ouabain inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Ouabain also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1092
  Mrv0541 02231215142D          

 43 48  0  0  1  0            999 V2000
    9.3991   -1.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2065   -2.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2557    0.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368    0.3612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5145    0.4967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9498   -2.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4384    2.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2402   -0.7810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8908    3.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5177   -2.8408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920   -2.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983   -0.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9702   -0.3281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.2588   -1.0662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 18  2  1  1  0  0  0
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 25  4  1  1  0  0  0
  5 28  1  0  0  0  0
 31  6  1  1  0  0  0
 35  6  1  1  0  0  0
  7 33  1  0  0  0  0
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 37 38  1  0  0  0  0
 38 40  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  6  0  0  0
M  END

HMDB0015224
     RDKit          3D
Ouabain
 85 90  0  0  0  0  0  0  0  0999 V2000
   -5.7145    1.4806    2.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    1.1001    1.3391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5537    1.8681    0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2078    1.3097   -0.4582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4305    0.1769   -0.3337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195    0.3517   -0.8367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2839    0.3663    0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308   -1.0447    0.8766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4761   -1.6207    0.6122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2102   -1.7855    0.0107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1812   -3.1371    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102   -4.1060    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302   -1.1323    0.0644 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.9083   -0.3532    2.3769 O   0  0  0  0  0  0  0  0  0  0  0  0
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 40 84  1  1
 41 85  1  0
M  END

1092
  Mrv0541 02231215142D          

 43 48  0  0  1  0            999 V2000
    9.3991   -1.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2065   -2.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4384    2.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9702    0.4969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6847    0.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1798    0.7483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6979   -1.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1798   -0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9570   -2.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4548   -0.2809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6612    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4411   -2.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2258    0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3991    1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6728   -0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6659   -1.6116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4361    1.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9523    2.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2212    1.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -1.6060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2226    2.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -2.0158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8081   -1.6005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5273   -0.3658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8112   -0.7755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5304    0.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5418    0.0019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2588   -1.0662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  1  0  0  0
 18  2  1  1  0  0  0
 19  3  1  6  0  0  0
 25  4  1  1  0  0  0
  5 28  1  0  0  0  0
 31  6  1  1  0  0  0
 35  6  1  1  0  0  0
  7 33  1  0  0  0  0
  7 36  1  0  0  0  0
  8 35  1  0  0  0  0
  8 39  1  0  0  0  0
  9 36  2  0  0  0  0
 37 10  1  6  0  0  0
 38 11  1  6  0  0  0
 40 12  1  1  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  0  0  0  0
 13 42  1  6  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 14 43  1  1  0  0  0
 15 16  1  0  0  0  0
 15 23  1  0  0  0  0
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 16 21  1  0  0  0  0
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 17 25  1  0  0  0  0
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 21 26  1  0  0  0  0
 21 32  1  1  0  0  0
 22 24  1  0  0  0  0
 23 26  1  0  0  0  0
 25 30  1  0  0  0  0
 27 31  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
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 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 40  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054617

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC[C@]3(O)C[C@H](C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]1(C)[C@H](CC[C@]21O)C1=CC(=O)OC1)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1

> <INCHI_KEY>
LPMXVESGRSUGHW-HBYQJFLCSA-N

> <FORMULA>
C29H44O12

> <MOLECULAR_WEIGHT>
584.6525

> <EXACT_MASS>
584.283276872

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
59.92556829434825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
-1.03

> <JCHEM_LOGP>
-2.7818058896666673

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.210394291601636

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.181446894362235

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8503841755458543

> <JCHEM_POLAR_SURFACE_AREA>
206.59999999999997

> <JCHEM_REFRACTIVITY>
140.83379999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ouabain

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015224
     RDKit          3D
Ouabain
 85 90  0  0  0  0  0  0  0  0999 V2000
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   -3.4305    0.1769   -0.3337 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2839    0.3663    0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1494    1.7259   -2.6176 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0516    0.7296    2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8685   -0.4322    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5258   -0.6925    2.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9184   -1.9060    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337    1.5143   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    1.4249    2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4823    2.7320   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056    3.7378   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -0.3400   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1227   -0.0160   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1266   -3.1606   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  4 36  1  0
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 25 20  1  0
  1 42  1  0
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  2 45  1  1
  4 46  1  6
  6 47  1  6
  7 48  1  0
  7 49  1  0
  8 50  1  1
  9 51  1  0
 11 52  1  0
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 13 55  1  6
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 18 60  1  0
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 18 62  1  0
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 25 65  1  0
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 26 67  1  0
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 27 70  1  0
 29 71  1  0
 30 72  1  1
 31 73  1  0
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 32 75  1  0
 32 76  1  0
 34 77  1  0
 35 78  1  0
 35 79  1  0
 36 80  1  6
 37 81  1  0
 38 82  1  6
 39 83  1  0
 40 84  1  1
 41 85  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1092                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      17.545  -2.152   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.452  -4.537   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.544   1.698   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   0.674   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      12.160   0.927   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.240  -3.773   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      19.485   5.352   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.915  -1.458   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      22.196   5.777   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.566  -5.303   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.905  -3.753   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.917  -0.673   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.878  -0.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.211  -1.382   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.545  -0.612   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.545   0.928   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.476  -1.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.464  -2.997   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.878   0.928   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.211   1.698   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.002   1.397   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.236  -2.986   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.002  -1.082   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.853  -3.799   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.049  -0.524   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.901   0.158   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.023  -3.844   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.488   0.147   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.545   2.468   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.589  -1.337   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.576  -3.008   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.481   2.860   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.578   4.108   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      20.946   3.334   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.909  -2.998   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.949   4.874   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.572  -3.763   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.242  -2.988   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.584  -0.683   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.248  -1.448   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.590   0.857   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0      15.945   0.004   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      17.283  -1.990   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   25                                                            
CONECT    5   28                                                            
CONECT    6   31   35                                                       
CONECT    7   33   36                                                       
CONECT    8   35   39                                                       
CONECT    9   36                                                            
CONECT   10   37                                                            
CONECT   11   38                                                            
CONECT   12   40                                                            
CONECT   13   14   17   19   42                                             
CONECT   14   13   15   22   43                                             
CONECT   15    1   14   16   23                                             
CONECT   16   15   20   21   29                                             
CONECT   17   13   18   25   28                                             
CONECT   18    2   17   24   27                                             
CONECT   19    3   13   20                                                  
CONECT   20   16   19                                                       
CONECT   21   16   26   32                                                  
CONECT   22   14   24                                                       
CONECT   23   15   26                                                       
CONECT   24   18   22                                                       
CONECT   25    4   17   30                                                  
CONECT   26   21   23                                                       
CONECT   27   18   31                                                       
CONECT   28    5   17                                                       
CONECT   29   16                                                            
CONECT   30   25   31                                                       
CONECT   31    6   27   30                                                  
CONECT   32   21   33   34                                                  
CONECT   33    7   32                                                       
CONECT   34   32   36                                                       
CONECT   35    6    8   37                                                  
CONECT   36    7    9   34                                                  
CONECT   37   10   35   38                                                  
CONECT   38   11   37   40                                                  
CONECT   39    8   40   41                                                  
CONECT   40   12   38   39                                                  
CONECT   41   39                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

COMPND    HMDB0015224
HETATM    1  C1  UNL     1      -5.714   1.481   2.795  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.592   1.100   1.339  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.554   1.868   0.756  1.00  0.00           O  
HETATM    4  C3  UNL     1      -4.208   1.310  -0.458  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.430   0.177  -0.334  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.119   0.352  -0.837  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.284   0.366   0.459  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.231  -1.045   0.877  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.476  -1.621   0.612  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.210  -1.786   0.011  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.181  -3.137   0.645  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.610  -4.106   0.128  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.130  -1.132   0.064  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.717  -0.809   1.389  1.00  0.00           C  
HETATM   15  O5  UNL     1       0.908  -0.353   2.377  1.00  0.00           O  
HETATM   16  C11 UNL     1       2.711   0.306   1.141  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.840  -0.219   0.338  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.859  -0.790   1.310  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.405   0.975  -0.418  1.00  0.00           C  
HETATM   20  C15 UNL     1       5.205   1.935   0.284  1.00  0.00           C  
HETATM   21  C16 UNL     1       5.552   2.040   1.535  1.00  0.00           C  
HETATM   22  C17 UNL     1       6.406   3.231   1.762  1.00  0.00           C  
HETATM   23  O6  UNL     1       6.880   3.570   2.877  1.00  0.00           O  
HETATM   24  O7  UNL     1       6.540   3.832   0.532  1.00  0.00           O  
HETATM   25  C18 UNL     1       5.847   3.123  -0.424  1.00  0.00           C  
HETATM   26  C19 UNL     1       5.088   0.274  -1.591  1.00  0.00           C  
HETATM   27  C20 UNL     1       3.907  -0.634  -2.034  1.00  0.00           C  
HETATM   28  C21 UNL     1       3.532  -1.250  -0.683  1.00  0.00           C  
HETATM   29  O8  UNL     1       4.529  -2.260  -0.559  1.00  0.00           O  
HETATM   30  C22 UNL     1       2.205  -1.921  -0.665  1.00  0.00           C  
HETATM   31  C23 UNL     1       1.689  -2.208  -2.047  1.00  0.00           C  
HETATM   32  C24 UNL     1       0.450  -1.461  -2.382  1.00  0.00           C  
HETATM   33  C25 UNL     1      -0.704  -1.705  -1.394  1.00  0.00           C  
HETATM   34  O9  UNL     1      -1.168  -2.993  -1.757  1.00  0.00           O  
HETATM   35  C26 UNL     1      -1.760  -0.744  -1.756  1.00  0.00           C  
HETATM   36  C27 UNL     1      -5.387   1.168  -1.339  1.00  0.00           C  
HETATM   37  O10 UNL     1      -5.149   1.726  -2.618  1.00  0.00           O  
HETATM   38  C28 UNL     1      -6.543   1.962  -0.769  1.00  0.00           C  
HETATM   39  O11 UNL     1      -6.281   3.313  -0.685  1.00  0.00           O  
HETATM   40  C29 UNL     1      -6.904   1.432   0.629  1.00  0.00           C  
HETATM   41  O12 UNL     1      -7.571   0.226   0.443  1.00  0.00           O  
HETATM   42  H1  UNL     1      -6.217   0.649   3.340  1.00  0.00           H  
HETATM   43  H2  UNL     1      -6.290   2.422   2.915  1.00  0.00           H  
HETATM   44  H3  UNL     1      -4.697   1.671   3.239  1.00  0.00           H  
HETATM   45  H4  UNL     1      -5.346   0.031   1.205  1.00  0.00           H  
HETATM   46  H5  UNL     1      -3.531   2.078  -0.948  1.00  0.00           H  
HETATM   47  H6  UNL     1      -2.010   1.388  -1.237  1.00  0.00           H  
HETATM   48  H7  UNL     1      -0.372   0.892   0.221  1.00  0.00           H  
HETATM   49  H8  UNL     1      -1.876   0.969   1.220  1.00  0.00           H  
HETATM   50  H9  UNL     1      -1.113  -1.252   1.959  1.00  0.00           H  
HETATM   51  H10 UNL     1      -2.509  -2.343  -0.007  1.00  0.00           H  
HETATM   52  H11 UNL     1      -1.206  -3.617   0.734  1.00  0.00           H  
HETATM   53  H12 UNL     1       0.038  -2.982   1.758  1.00  0.00           H  
HETATM   54  H13 UNL     1       1.040  -4.606   0.872  1.00  0.00           H  
HETATM   55  H14 UNL     1       1.123  -0.156  -0.535  1.00  0.00           H  
HETATM   56  H15 UNL     1       2.354  -1.675   1.745  1.00  0.00           H  
HETATM   57  H16 UNL     1       0.840   0.627   2.477  1.00  0.00           H  
HETATM   58  H17 UNL     1       3.052   0.730   2.105  1.00  0.00           H  
HETATM   59  H18 UNL     1       2.164   1.111   0.564  1.00  0.00           H  
HETATM   60  H19 UNL     1       5.869  -0.432   1.146  1.00  0.00           H  
HETATM   61  H20 UNL     1       4.526  -0.693   2.382  1.00  0.00           H  
HETATM   62  H21 UNL     1       4.918  -1.906   1.186  1.00  0.00           H  
HETATM   63  H22 UNL     1       3.534   1.514  -0.925  1.00  0.00           H  
HETATM   64  H23 UNL     1       5.307   1.425   2.386  1.00  0.00           H  
HETATM   65  H24 UNL     1       6.482   2.732  -1.252  1.00  0.00           H  
HETATM   66  H25 UNL     1       5.006   3.738  -0.804  1.00  0.00           H  
HETATM   67  H26 UNL     1       5.892  -0.340  -1.185  1.00  0.00           H  
HETATM   68  H27 UNL     1       5.407   0.946  -2.382  1.00  0.00           H  
HETATM   69  H28 UNL     1       4.386  -1.362  -2.717  1.00  0.00           H  
HETATM   70  H29 UNL     1       3.123  -0.016  -2.460  1.00  0.00           H  
HETATM   71  H30 UNL     1       4.127  -3.161  -0.675  1.00  0.00           H  
HETATM   72  H31 UNL     1       2.365  -2.886  -0.150  1.00  0.00           H  
HETATM   73  H32 UNL     1       1.545  -3.288  -2.270  1.00  0.00           H  
HETATM   74  H33 UNL     1       2.438  -1.887  -2.836  1.00  0.00           H  
HETATM   75  H34 UNL     1       0.610  -0.366  -2.517  1.00  0.00           H  
HETATM   76  H35 UNL     1       0.079  -1.817  -3.365  1.00  0.00           H  
HETATM   77  H36 UNL     1      -1.761  -2.958  -2.546  1.00  0.00           H  
HETATM   78  H37 UNL     1      -2.726  -1.247  -2.077  1.00  0.00           H  
HETATM   79  H38 UNL     1      -1.511  -0.215  -2.736  1.00  0.00           H  
HETATM   80  H39 UNL     1      -5.760   0.125  -1.438  1.00  0.00           H  
HETATM   81  H40 UNL     1      -4.399   2.347  -2.589  1.00  0.00           H  
HETATM   82  H41 UNL     1      -7.472   1.838  -1.376  1.00  0.00           H  
HETATM   83  H42 UNL     1      -6.861   3.878  -1.221  1.00  0.00           H  
HETATM   84  H43 UNL     1      -7.550   2.104   1.183  1.00  0.00           H  
HETATM   85  H44 UNL     1      -8.560   0.396   0.510  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3   40   45
CONECT    3    4
CONECT    4    5   36   46
CONECT    5    6
CONECT    6    7   35   47
CONECT    7    8   48   49
CONECT    8    9   10   50
CONECT    9   51
CONECT   10   11   13   33
CONECT   11   12   52   53
CONECT   12   54
CONECT   13   14   30   55
CONECT   14   15   16   56
CONECT   15   57
CONECT   16   17   58   59
CONECT   17   18   19   28
CONECT   18   60   61   62
CONECT   19   20   26   63
CONECT   20   21   21   25
CONECT   21   22   64
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   65   66
CONECT   26   27   67   68
CONECT   27   28   69   70
CONECT   28   29   30
CONECT   29   71
CONECT   30   31   72
CONECT   31   32   73   74
CONECT   32   33   75   76
CONECT   33   34   35
CONECT   34   77
CONECT   35   78   79
CONECT   36   37   38   80
CONECT   37   81
CONECT   38   39   40   82
CONECT   39   83
CONECT   40   41   84
CONECT   41   85
END

HMDB0015224
     RDKit          3D
Ouabain
 85 90  0  0  0  0  0  0  0  0999 V2000
   -5.7145    1.4806    2.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    1.1001    1.3391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5537    1.8681    0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2078    1.3097   -0.4582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4305    0.1769   -0.3337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195    0.3517   -0.8367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2839    0.3663    0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308   -1.0447    0.8766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4761   -1.6207    0.6122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2102   -1.7855    0.0107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1812   -3.1371    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102   -4.1060    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302   -1.1323    0.0644 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7169   -0.8092    1.3887 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9083   -0.3532    2.3769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7107    0.3065    1.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399   -0.2187    0.3376 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8589   -0.7901    1.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050    0.9749   -0.4178 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2054    1.9355    0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5523    2.0401    1.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061    3.2314    1.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8803    3.5697    2.8768 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5399    3.8323    0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468    3.1230   -0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876    0.2737   -1.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -0.6336   -2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317   -1.2500   -0.6833 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5287   -2.2605   -0.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2052   -1.9208   -0.6649 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6893   -2.2081   -2.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -1.4607   -2.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7040   -1.7054   -1.3938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1678   -2.9929   -1.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600   -0.7439   -1.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3873    1.1677   -1.3385 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1494    1.7259   -2.6176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5431    1.9618   -0.7690 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2808    3.3130   -0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9038    1.4319    0.6286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5712    0.2264    0.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2175    0.6494    3.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2896    2.4216    2.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6972    1.6710    3.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3459    0.0311    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5314    2.0780   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096    1.3877   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720    0.8923    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765    0.9689    1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1134   -1.2518    1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088   -2.3426   -0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -3.6170    0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378   -2.9816    1.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0402   -4.6057    0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1228   -0.1561   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540   -1.6745    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    0.6272    2.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516    0.7296    2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    1.1111    0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8685   -0.4322    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5258   -0.6925    2.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9184   -1.9060    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337    1.5143   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    1.4249    2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4823    2.7320   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056    3.7378   -0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -0.3400   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4068    0.9455   -2.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3857   -1.3620   -2.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.0160   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1266   -3.1606   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654   -2.8864   -0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5453   -3.2883   -2.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -1.8870   -2.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096   -0.3662   -2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -1.8170   -3.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -2.9580   -2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7260   -1.2468   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106   -0.2154   -2.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7599    0.1251   -1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3988    2.3465   -2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4724    1.8376   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8609    3.8779   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5504    2.1043    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5596    0.3961    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1 44  1  0
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M  END

Synonyms

Value	Source
3-(alpha-L-Rhamnopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide	ChEBI
g-Strophanthin	ChEBI
Ouabagenin L-rhamnoside	ChEBI
Ouabagenin-L-rhamnosid	ChEBI
Ouabain anhydrous	ChEBI
Ouabaine	ChEBI
Oubain	ChEBI
Strodival	ChEBI
Ouabain octahydrate	Kegg
3-(a-L-Rhamnopyranosyloxy)-1b,5b,11a,14,19-pentahydroxy-5b-card-20(22)-enolide	Generator
3-(Α-L-rhamnopyranosyloxy)-1β,5β,11α,14,19-pentahydroxy-5β-card-20(22)-enolide	Generator
Ouabain octahydric acid	Generator
Ouabain, octahydrate	HMDB
Strophanthin g	HMDB
Strophanthin-g	HMDB
K, Acolongifloroside	HMDB
Acocantherin	HMDB
Acolongifloroside K	HMDB
g Strophanthin	HMDB

Molecular Formula

C₂₉H₄₄O₁₂

Average Mass

584.6525

Monoisotopic Mass

584.283276872

IUPAC Name

4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

Traditional Name

ouabain

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(O)C[C@H](C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]1(C)[C@H](CC[C@]21O)C1=CC(=O)OC1)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1

InChI Key

LPMXVESGRSUGHW-HBYQJFLCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Phenylpropane
Phenylmethylamine
Benzylamine
Aralkylamine
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tertiary amine (CHEBI:3238 )
naphthalenes (CHEBI:3238 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.61 g/L	ALOGPS
logP	-1	ALOGPS
logP	-2.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.83 m³·mol⁻¹	ChemAxon
Polarizability	59.93 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192113	Solute carrier organic anion transporter family member 1C1	Transporter	Q9NYB5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0192962	Sodium/potassium-transporting ATPase subunit alpha-1	Unknown	P05023	Homo sapiens
MMDBp0193110	Cytochrome P450 1A1	Unknown	P04798	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0194944	Solute carrier organic anion transporter family member 4C1	Transporter	Q6ZQN7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human ; Human feces

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0015224

DrugBank ID

DB01092

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00003633

Chemspider ID

388599

KEGG Compound ID

C01443

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ouabain

METLIN ID

Not Available

PubChem Compound

439501

PDB ID

OBN

ChEBI ID

472805

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, Mathews WR, Ludens JH: Identification and characterization of a ouabain-like compound from human plasma. Proc Natl Acad Sci U S A. 1991 Jul 15;88(14):6259-63. doi: 10.1073/pnas.88.14.6259. [PubMed:1648735 ]
Laredo J, Hamilton BP, Hamlyn JM: Ouabain is secreted by bovine adrenocortical cells. Endocrinology. 1994 Aug;135(2):794-7. doi: 10.1210/endo.135.2.8033829. [PubMed:8033829 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Gao J, Wymore RS, Wang Y, Gaudette GR, Krukenkamp IB, Cohen IS, Mathias RT: Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. J Gen Physiol. 2002 Apr;119(4):297-312. doi: 10.1085/jgp.20028501. [PubMed:11929882 ]
Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP: 11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. Ann N Y Acad Sci. 2003 Apr;986:685-93. doi: 10.1111/j.1749-6632.2003.tb07283.x. [PubMed:12763919 ]
TRUNZLER G, SCHULER E: [Comparative studies on the effect of a Crataegus extract, of digitoxin, digoxin and gstrophanthin on the isolated mammalian heart]. Arzneimittelforschung. 1962 Feb;12:198-202. [PubMed:13922712 ]
Saunders R, Scheiner-Bobis G: Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. Eur J Biochem. 2004 Mar;271(5):1054-62. doi: 10.1111/j.1432-1033.2004.04012.x. [PubMed:15009217 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for ouabain (MMDBc0054617)

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