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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:53:08 UTC

Update Date

2022-09-22 18:34:53 UTC

HMDB ID

HMDB0341392

Secondary Accession Numbers

None

Metabolite Identification

Common Name

S-(3-hydroxypropyl)mercapturic acid

Description

N-Acetyl-S-(3-hydroxypropyl)cysteine, also known as 3-HMPA or 3-hydroxypropylmercapturic acid, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. Based on a literature review very few articles have been published on N-Acetyl-S-(3-hydroxypropyl)cysteine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092223312D          

 15 14  0  0  1  0            999 V2000
    4.4780    5.1315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    4.3519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9379    4.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    3.8842    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    3.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    4.9755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    4.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683    4.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283    3.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4780    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  0  0  0
 10 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341392

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](CSCCCO)(N=C(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO4S/c1-6(11)9-7(8(12)13)5-14-4-2-3-10/h7,10H,2-5H2,1H3,(H,9,11)(H,12,13)/t7-/m0/s1

> <INCHI_KEY>
FMWPQZPFBAHHMB-ZETCQYMHSA-N

> <FORMULA>
C8H15NO4S

> <MOLECULAR_WEIGHT>
221.27

> <EXACT_MASS>
221.072179141

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.86279968257861

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-[(3-hydroxypropyl)sulfanyl]propanoic acid

> <JCHEM_LOGP>
-0.23861964266666708

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.094265597265659

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.952512012957678

> <JCHEM_PKA_STRONGEST_BASIC>
1.1455134547187191

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
54.047000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-[(3-hydroxypropyl)sulfanyl]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       8.359   9.579   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       8.863   8.124   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.351   8.415   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       6.343   7.250   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       4.830   7.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.822   6.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310   6.668   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.302   5.504   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       9.871   9.288   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.383   8.997   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.392  10.161   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.888   7.541   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.367   6.668   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.879   6.377   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.359   5.504   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9   13                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Acetamido-3-(3'-hydroxypropylthio)propanoic acid	MeSH
3-HMPA	MeSH
3-Hydroxypropylmercapturic acid	MeSH
S-(3-Hydroxypropyl)cysteine N-acetate	MeSH

Chemical Formula

C₈H₁₅NO₄S

Average Molecular Weight

221.27

Monoisotopic Molecular Weight

221.072179141

IUPAC Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-[(3-hydroxypropyl)sulfanyl]propanoic acid

Traditional Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-[(3-hydroxypropyl)sulfanyl]propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CSCCCO)(N=C(C)O)C(O)=O

InChI Identifier

InChI=1S/C8H15NO4S/c1-6(11)9-7(8(12)13)5-14-4-2-3-10/h7,10H,2-5H2,1H3,(H,9,11)(H,12,13)/t7-/m0/s1

InChI Key

FMWPQZPFBAHHMB-ZETCQYMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
Carbonyl group
Organic oxygen compound
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-0.24	ChemAxon
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	1.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.05 m³·mol⁻¹	ChemAxon
Polarizability	22.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

106404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119083

PDB ID

Not Available

ChEBI ID

Not Available

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

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for S-(3-hydroxypropyl)mercapturic acid (HMDB0341392)

MOL for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

3D MOL for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

3D SDF for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

3D-SDF for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

PDB for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

3D PDB for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

SMILES for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

INCHI for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

Structure for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

3D Structure for HMDB0341392 (S-(3-hydroxypropyl)mercapturic acid)

Predicted Kovats Retention Indices