Showing metabocard for D-Tryptophan (MMDBc0000781)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:54:48 UTC
Update Date2024-10-15 18:55:24 UTC
Metabolite IDMMDBc0000781
Metabolite Identification
Common NameD-Tryptophan
DescriptionTryptophan (Trp or W) (sold for medical use as Tryptan) is one of the 20 standard amino acids. Its distinguishing structural characteristic is its indole functional group. The D-stereoisomer is occasionally found in naturally produced peptides (e.g. contryphan, the marine venom peptide).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9253d87678>


  Mrv1652303202019012D          

 15 16  0  0  1  0            999 V2000
    0.0032   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -1.2545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -0.2625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4321   -1.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9253d87678>

HMDB0013609
     RDKit          3D
D-Tryptophan
 27 28  0  0  0  0  0  0  0  0999 V2000
    3.1286    1.5753    0.3506 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995    0.7229    0.0983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1674    0.5560    1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180   -0.3175    1.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1462   -1.6314    1.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360   -2.0561    0.9847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647   -1.0439    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820   -0.9327   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5981    0.2311   -0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7461    1.3133   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.2171   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265    0.0408    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790   -0.5762   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6580   -1.4685   -0.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220   -0.8188   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    1.5906   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    2.5482    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.1899   -0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146    0.1832    2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    1.5791    1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -2.2249    1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658   -2.9968    1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8169   -1.8238   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5384    0.3098   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    2.2420   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9008    2.0838   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3544   -1.4927   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 12  4  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 15 27  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9253d87678>


  Mrv1652303202019012D          

 15 16  0  0  1  0            999 V2000
    0.0032   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -1.2545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -0.2625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4321   -1.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000781

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@H](CC1=CNC2=C1C=CC=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1

> <INCHI_KEY>
QIVBCDIJIAJPQS-SECBINFHSA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.2252

> <EXACT_MASS>
204.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.167931614481088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-1.0854569138833579

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.1565885064574

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5439286383469866

> <JCHEM_PKA_STRONGEST_BASIC>
9.396082567807317

> <JCHEM_POLAR_SURFACE_AREA>
79.11000000000001

> <JCHEM_REFRACTIVITY>
56.20280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-tryptophan

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9253d87678>

HMDB0013609
     RDKit          3D
D-Tryptophan
 27 28  0  0  0  0  0  0  0  0999 V2000
    3.1286    1.5753    0.3506 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995    0.7229    0.0983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1674    0.5560    1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180   -0.3175    1.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1462   -1.6314    1.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360   -2.0561    0.9847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647   -1.0439    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820   -0.9327   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5981    0.2311   -0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7461    1.3133   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.2171   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265    0.0408    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790   -0.5762   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6580   -1.4685   -0.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220   -0.8188   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    1.5906   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    2.5482    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.1899   -0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146    0.1832    2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    1.5791    1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -2.2249    1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658   -2.9968    1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8169   -1.8238   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5384    0.3098   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    2.2420   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9008    2.0838   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3544   -1.4927   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 12  4  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 15 27  1  0
M  END
Download

PDB for #<Metabolite:0x00007f9253d87678>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.006  -0.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.155  -2.022   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.661  -2.342   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.431  -1.008   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.401   0.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.877   1.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.938  -0.688   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.414   0.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.383   1.921   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.007   1.820   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.007   0.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.341  -0.490   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.673  -0.490   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.673  -2.030   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.340   0.280   0.000  0.00  0.00           C+0
CONECT    1    2    5   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    9                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8                                                       
CONECT   10   11                                                            
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    1                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
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3D PDB for #<Metabolite:0x00007f9253d87678>

COMPND    HMDB0013609
HETATM    1  N1  UNL     1       3.129   1.575   0.351  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.000   0.723   0.098  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.167   0.556   1.352  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.018  -0.318   1.075  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.146  -1.631   1.431  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.336  -2.056   0.985  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.965  -1.044   0.338  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.182  -0.933  -0.301  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.598   0.231  -0.893  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.746   1.313  -0.832  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.539   1.217  -0.204  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.126   0.041   0.391  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.479  -0.576  -0.400  1.00  0.00           C  
HETATM   14  O1  UNL     1       1.658  -1.468  -0.683  1.00  0.00           O  
HETATM   15  O2  UNL     1       3.822  -0.819  -0.556  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.711   1.591  -0.523  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.868   2.548   0.608  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.333   1.190  -0.686  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.815   0.183   2.155  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.837   1.579   1.650  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.550  -2.225   1.972  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.766  -2.997   1.085  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.817  -1.824  -0.318  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.538   0.310  -1.384  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.080   2.242  -1.306  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.901   2.084  -0.177  1.00  0.00           H  
HETATM   27  H12 UNL     1       4.354  -1.493  -0.045  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3   13   18
CONECT    3    4   19   20
CONECT    4    5    5   12
CONECT    5    6   21
CONECT    6    7   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   13   14   14   15
CONECT   15   27
END
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SMILES for #<Metabolite:0x00007f9253d87678>

N[C@H](CC1=CNC2=C1C=CC=C2)C(O)=O
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INCHI for #<Metabolite:0x00007f9253d87678>

InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1
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Synonyms
ValueSource
(2R)-2-Amino-3-(1H-indol-3-yl)propanoic acidChEBI
(R)-TryptophanChEBI
DTRChEBI
(2R)-2-Amino-3-(1H-indol-3-yl)propanoateGenerator
(+)-TryptophanHMDB
(R)-(+)-2-amino-3-(3-Indolyl)propionic acidHMDB
(R)-2-amino-3-(3-Indolyl)propionic acidHMDB
D-(+)-TryptophanHMDB
D-alpha-amino-3-Indolepropionic acidHMDB
D-TryptophaneHMDB
D-TrytophaneHMDB
delta-(+)-TryptophanHMDB
delta-alpha-amino-3-Indolepropionic acidHMDB
delta-TryptophaneHMDB
delta-TrytophaneHMDB
DL-TryptophanHMDB
H-D-TRP-OHHMDB
H-delta-TRP-OHHMDB
TryptophanHMDB
Molecular FormulaC11H12N2O2
Average Mass204.2252
Monoisotopic Mass204.089877638
IUPAC Name(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameD-tryptophan
CAS Registry NumberNot Available
SMILES
N[C@H](CC1=CNC2=C1C=CC=C2)C(O)=O
InChI Identifier
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1
InChI KeyQIVBCDIJIAJPQS-SECBINFHSA-N