Showing metabocard for 6-aminopenicillanic acid (MMDBc0016197)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-05-15 06:52:54 UTC
Update Date2025-01-16 22:04:07 UTC
Metabolite IDMMDBc0016197
Metabolite Identification
Common Name6-aminopenicillanic acid
Description6-Aminopenicillanic acid is a metabolite of penicillin v; penicillin g.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9258048e80>


  Mrv0541 06151311042D          

 14 15  0  0  1  0            999 V2000
    2.5600    0.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469    1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5600    1.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620    0.6773    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773    0.9323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1477    0.9323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7310    0.3489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477    1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    2.3406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773    1.7573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620    2.0122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7169    2.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649    3.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  6  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9258048e80>

HMDB0060618
     RDKit          3D
6-Aminopenicillanic acid
 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.9550   -2.2153    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9086   -0.9554   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0008   -0.9502   -1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -0.7683   -1.2622 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1739    0.8241   -0.5016 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4832    0.7884    0.2414 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1287   -0.4909    0.2668 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135    1.0875    1.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    1.5293    2.5602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213    0.7002    0.7496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    0.2986    0.4811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6625    1.4081   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    1.3209   -0.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    2.6200   -0.3462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680   -2.1234    1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -2.5001    0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473   -3.0413   -0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0133   -0.9629   -0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842   -0.0718   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9097   -1.8420   -2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783    1.7044   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1177    1.6554   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0769   -0.5121   -0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0755   -0.9610    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405    0.0581    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    3.3998    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  2  1  0
 10  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  6
  6 22  1  6
  7 23  1  0
  7 24  1  0
 11 25  1  1
 14 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9258048e80>


  Mrv0541 06151311042D          

 14 15  0  0  1  0            999 V2000
    2.5600    0.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469    1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5600    1.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620    0.6773    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773    0.9323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1477    0.9323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7310    0.3489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477    1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    2.3406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773    1.7573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620    2.0122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7169    2.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649    3.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  6  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016197

> <DATABASE_NAME>
MIME

> <SMILES>
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1

> <INCHI_KEY>
NGHVIOIJCVXTGV-ALEPSDHESA-N

> <FORMULA>
C8H12N2O3S

> <MOLECULAR_WEIGHT>
216.257

> <EXACT_MASS>
216.05686295

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.698966400238533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-2.8378366429456663

> <ALOGPS_LOGS>
-0.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.433548704443023

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.415152063079619

> <JCHEM_PKA_STRONGEST_BASIC>
7.403258608746982

> <JCHEM_POLAR_SURFACE_AREA>
83.63

> <JCHEM_REFRACTIVITY>
50.36210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
penin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9258048e80>

HMDB0060618
     RDKit          3D
6-Aminopenicillanic acid
 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.9550   -2.2153    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9086   -0.9554   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0008   -0.9502   -1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -0.7683   -1.2622 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1739    0.8241   -0.5016 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4832    0.7884    0.2414 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1287   -0.4909    0.2668 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135    1.0875    1.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    1.5293    2.5602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213    0.7002    0.7496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    0.2986    0.4811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6625    1.4081   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    1.3209   -0.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230    2.6200   -0.3462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680   -2.1234    1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -2.5001    0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473   -3.0413   -0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0133   -0.9629   -0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842   -0.0718   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9097   -1.8420   -2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783    1.7044   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1177    1.6554   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0769   -0.5121   -0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0755   -0.9610    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405    0.0581    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    3.3998    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  2  1  0
 10  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  6
  6 22  1  6
  7 23  1  0
  7 24  1  0
 11 25  1  1
 14 26  1  0
M  END
Download

PDB for #<Metabolite:0x00007f9258048e80>

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       4.779   1.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.634   2.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.779   3.541   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       2.729   1.264   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       1.264   1.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.276   1.740   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.365   0.651   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.276   3.280   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.365   4.369   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       1.264   3.280   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.729   3.756   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.205   5.221   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.174   6.365   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.711   5.541   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   11                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for #<Metabolite:0x00007f9258048e80>

COMPND    HMDB0060618
HETATM    1  C1  UNL     1      -0.955  -2.215   0.433  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.909  -0.955  -0.361  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.001  -0.950  -1.396  1.00  0.00           C  
HETATM    4  S1  UNL     1       0.681  -0.768  -1.262  1.00  0.00           S  
HETATM    5  C4  UNL     1       1.174   0.824  -0.502  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.483   0.788   0.241  1.00  0.00           C  
HETATM    7  N1  UNL     1       3.129  -0.491   0.267  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.613   1.088   1.415  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.925   1.529   2.560  1.00  0.00           O  
HETATM   10  N2  UNL     1       0.421   0.700   0.750  1.00  0.00           N  
HETATM   11  C7  UNL     1      -0.919   0.299   0.481  1.00  0.00           C  
HETATM   12  C8  UNL     1      -1.663   1.408  -0.134  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.871   1.321  -0.487  1.00  0.00           O  
HETATM   14  O3  UNL     1      -1.023   2.620  -0.346  1.00  0.00           O  
HETATM   15  H1  UNL     1      -1.768  -2.123   1.179  1.00  0.00           H  
HETATM   16  H2  UNL     1       0.017  -2.500   0.880  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.247  -3.041  -0.266  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.013  -0.963  -0.962  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.884  -0.072  -2.083  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.910  -1.842  -2.034  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.978   1.704  -1.105  1.00  0.00           H  
HETATM   22  H8  UNL     1       3.118   1.655  -0.045  1.00  0.00           H  
HETATM   23  H9  UNL     1       4.077  -0.512  -0.138  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.076  -0.961   1.201  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.441   0.058   1.431  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.089   3.400   0.283  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4   11
CONECT    3   18   19   20
CONECT    4    5
CONECT    5    6   10   21
CONECT    6    7    8   22
CONECT    7   23   24
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   25
CONECT   12   13   13   14
CONECT   14   26
END
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SMILES for #<Metabolite:0x00007f9258048e80>

CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
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INCHI for #<Metabolite:0x00007f9258048e80>

InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
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Synonyms
ValueSource
(+)-6-Aminopenicillanic acidChEBI
(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-Aminopenicillamine acidChEBI
6-AminopenicillanateChEBI
6-APAChEBI
6-ApsChEBI
6beta-Aminopenicillanic acidChEBI
Aminopenicillanic acidChEBI
PenicinChEBI
PeninChEBI
Phenacyl 6-aminopenicillinateChEBI
(+)-6-AminopenicillanateGenerator
(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6b-AminopenicillanateGenerator
6b-Aminopenicillanic acidGenerator
6beta-AminopenicillanateGenerator
6Β-aminopenicillanateGenerator
6Β-aminopenicillanic acidGenerator
AminopenicillanateGenerator
Phenacyl 6-aminopenicillinic acidGenerator
6-APA CPDHMDB
Aminopenicillanic acid, potassium saltHMDB
Aminopenicillanic acid, sodium saltHMDB
Molecular FormulaC8H12N2O3S
Average Mass216.257
Monoisotopic Mass216.05686295
IUPAC Name(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namepenin
CAS Registry NumberNot Available
SMILES
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
InChI Identifier
InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChI KeyNGHVIOIJCVXTGV-ALEPSDHESA-N