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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:21:21 UTC

Update Date

2022-09-22 18:35:03 UTC

HMDB ID

HMDB0341149

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cys-Trp-Ala

Description

Cys-Trp-Ala belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Based on a literature review very few articles have been published on Cys-Trp-Ala.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092221592D          

 29 30  0  0  1  0            999 V2000
   -1.4950   -4.8469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020   -5.0184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6288   -2.9346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0273   -1.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -0.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -1.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -0.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  4  0  0  0
  6  8  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  4  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  6  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END


  Mrv1652309092221592D          

 29 30  0  0  1  0            999 V2000
   -1.4950   -4.8469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020   -5.0184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6288   -2.9346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0273   -1.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -0.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -1.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -0.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  4  0  0  0
  6  8  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  4  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  6  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341149

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](N)(CS)C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=N[C@@]([H])(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N4O4S/c1-9(17(24)25)20-16(23)14(21-15(22)12(18)8-26)6-10-7-19-13-5-3-2-4-11(10)13/h2-5,7,9,12,14,19,26H,6,8,18H2,1H3,(H,20,23)(H,21,22)(H,24,25)/t9-,12-,14-/m0/s1

> <INCHI_KEY>
YFKWIIRWHGKSQQ-WFBYXXMGSA-N

> <FORMULA>
C17H22N4O4S

> <MOLECULAR_WEIGHT>
378.45

> <EXACT_MASS>
378.136176378

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
38.75829101565136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}propanoic acid

> <JCHEM_LOGP>
-0.837979081873852

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.8922134931084953

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2459706761724627

> <JCHEM_PKA_STRONGEST_BASIC>
9.105784962179518

> <JCHEM_POLAR_SURFACE_AREA>
144.29000000000002

> <JCHEM_REFRACTIVITY>
99.5673

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0      -2.791  -9.048   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.284  -8.727   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.821  -7.903   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      -4.297  -9.368   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       1.174  -5.478   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      -2.393  -3.509   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -3.424  -2.365   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      -1.918  -2.045   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      -2.948  -0.900   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.930  -2.685   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.406  -4.150   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.961  -1.541   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   21                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12   15                                                  
CONECT   21    9   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂N₄O₄S

Average Molecular Weight

378.45

Monoisotopic Molecular Weight

378.136176378

IUPAC Name

(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}propanoic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2R)-2-amino-1-hydroxy-3-sulfanylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CS)C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=N[C@@]([H])(C)C(O)=O

InChI Identifier

InChI=1S/C17H22N4O4S/c1-9(17(24)25)20-16(23)14(21-15(22)12(18)8-26)6-10-7-19-13-5-3-2-4-11(10)13/h2-5,7,9,12,14,19,26H,6,8,18H2,1H3,(H,20,23)(H,21,22)(H,24,25)/t9-,12-,14-/m0/s1

InChI Key

YFKWIIRWHGKSQQ-WFBYXXMGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alanine or derivatives
3-alkylindole
Alpha-amino acid or derivatives
Indole or derivatives
Indole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Alkylthiol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.84	ChemAxon
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	144.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	38.76 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

145454901

PDB ID

Not Available

ChEBI ID

161741

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for Cys-Trp-Ala (HMDB0341149)

MOL for HMDB0341149 (Cys-Trp-Ala)

3D MOL for HMDB0341149 (Cys-Trp-Ala)

3D SDF for HMDB0341149 (Cys-Trp-Ala)

3D-SDF for HMDB0341149 (Cys-Trp-Ala)

PDB for HMDB0341149 (Cys-Trp-Ala)

3D PDB for HMDB0341149 (Cys-Trp-Ala)

SMILES for HMDB0341149 (Cys-Trp-Ala)

INCHI for HMDB0341149 (Cys-Trp-Ala)

Structure for HMDB0341149 (Cys-Trp-Ala)

3D Structure for HMDB0341149 (Cys-Trp-Ala)

Predicted Kovats Retention Indices