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Showing metabocard for 3-Methylthiopropionic acid (HMDB0001527)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:45 UTC
HMDB IDHMDB0001527
Secondary Accession Numbers
  • HMDB01527
Metabolite Identification
Common Name3-Methylthiopropionic acid
Description3-Methylthiopropionic acid, also known as 3-(methylsulfanyl)propanoate or 3-methylthiopropanoate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Based on a literature review a significant number of articles have been published on 3-Methylthiopropionic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001527 (3-Methylthiopropionic acid)

  Mrv0541 02231219122D          

  7  6  0  0  0  0            999 V2000
   -0.2034   -0.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    0.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    0.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -0.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    0.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240   -0.3552    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9377    0.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for HMDB0001527 (3-Methylthiopropionic acid)

HMDB0001527
     RDKit          3D
3-Methylthiopropionic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.6838    0.4315   -0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.6288   -0.2892 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.9316   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845   -0.5604   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139    0.2695    0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -0.1293    2.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    1.4810    0.7382 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -0.6148   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203    1.0667    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387    0.7975   -1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -1.5617   -1.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -1.4851    0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -1.4824   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941   -0.0604   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.1507    0.0788 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  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0001527 (3-Methylthiopropionic acid)

  Mrv0541 02231219122D          

  7  6  0  0  0  0            999 V2000
   -0.2034   -0.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    0.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    0.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -0.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    0.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240   -0.3552    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9377    0.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001527

> <DATABASE_NAME>
hmdb

> <SMILES>
CSCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2S/c1-7-3-2-4(5)6/h2-3H2,1H3,(H,5,6)

> <INCHI_KEY>
CAOMCZAIALVUPA-UHFFFAOYSA-N

> <FORMULA>
C4H8O2S

> <MOLECULAR_WEIGHT>
120.17

> <EXACT_MASS>
120.02450019

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.221708609515161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(methylsulfanyl)propanoic acid

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.8347975820000002

> <ALOGPS_LOGS>
-0.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676434451839513

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
29.7249

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylthiopropionic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001527 (3-Methylthiopropionic acid)

HMDB0001527
     RDKit          3D
3-Methylthiopropionic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.6838    0.4315   -0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.6288   -0.2892 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.9316   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845   -0.5604   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139    0.2695    0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4934   -0.1293    2.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    1.4810    0.7382 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -0.6148   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203    1.0667    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387    0.7975   -1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -1.5617   -1.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -1.4851    0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -1.4824   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941   -0.0604   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.1507    0.0788 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  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0001527 (3-Methylthiopropionic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.380  -0.663   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.712   0.109   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.953   0.109   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.051  -0.663   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.712   1.648   0.000  0.00  0.00           O+0
HETATM    6  S   UNK     0       2.285  -0.663   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       3.617   0.109   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1    6                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    3    7                                                       
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0001527 (3-Methylthiopropionic acid)

COMPND    HMDB0001527
HETATM    1  C1  UNL     1       2.684   0.432  -0.356  1.00  0.00           C  
HETATM    2  S1  UNL     1       0.912   0.629  -0.289  1.00  0.00           S  
HETATM    3  C2  UNL     1      -0.003  -0.932  -0.240  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.484  -0.560  -0.230  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.814   0.269   0.953  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.493  -0.129   2.080  1.00  0.00           O  
HETATM    7  O2  UNL     1      -2.474   1.481   0.738  1.00  0.00           O  
HETATM    8  H1  UNL     1       3.017  -0.615  -0.184  1.00  0.00           H  
HETATM    9  H2  UNL     1       3.120   1.067   0.457  1.00  0.00           H  
HETATM   10  H3  UNL     1       3.139   0.797  -1.313  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.168  -1.562  -1.115  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.220  -1.485   0.696  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.106  -1.482  -0.139  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.794  -0.060  -1.138  1.00  0.00           H  
HETATM   15  H8  UNL     1      -2.090   2.151   0.079  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for HMDB0001527 (3-Methylthiopropionic acid)

CSCCC(O)=O
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INCHI for HMDB0001527 (3-Methylthiopropionic acid)

InChI=1S/C4H8O2S/c1-7-3-2-4(5)6/h2-3H2,1H3,(H,5,6)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Methylthiopropanoic acidChEBI
3-(Methylthio)propionic acidKegg
3-MethylthiopropionateKegg
3-(Methylsulfanyl)propanoateKegg
3-MethylthiopropanoateGenerator
3-(Methylthio)propionateGenerator
3-(Methylsulfanyl)propanoic acidGenerator
3-(Methylsulphanyl)propanoateGenerator
3-(Methylsulphanyl)propanoic acidGenerator
3-MethylmercaptopropionateMeSH
3-Methylthiopropionate sodium saltMeSH
4-ThiapentanoateHMDB
4-Thiapentanoic acidHMDB
3-Methylthiopropionic acidGenerator
3-Methyl-thiopropionateGenerator, HMDB
Chemical FormulaC4H8O2S
Average Molecular Weight120.17
Monoisotopic Molecular Weight120.02450019
IUPAC Name3-(methylsulfanyl)propanoic acid
Traditional Name3-methylthiopropionic acid
CAS Registry Number646-01-5
SMILES
CSCCC(O)=O
InChI Identifier
InChI=1S/C4H8O2S/c1-7-3-2-4(5)6/h2-3H2,1H3,(H,5,6)
InChI KeyCAOMCZAIALVUPA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point244.00 to 247.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility67370 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.458 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
UrineDetected and Quantified0.036 +/- 0.009 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified0.097 +/- 0.022 umol/mmol creatinineAdult (>18 years old)BothLiver Cirrhosis details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Cirrhosis
  1. Yoshida Y: [Analysis of methionine metabolism studied by the gas chromatographic determination of 3-methylthiopropionate in urine and its clinical application]. Hokkaido Igaku Zasshi. 1985 Mar;60(2):183-94. [PubMed:3997054 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022672
KNApSAcK IDC00001194
Chemspider ID547
KEGG Compound IDC08276
BioCyc IDCPD-7672
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6300
PubChem Compound563
PDB IDNot Available
ChEBI ID1438
Food Biomarker OntologyNot Available
VMH IDC08276
MarkerDB IDMDB00013440
Good Scents IDrw1047451
References
Synthesis ReferenceWhitehead, Ian M.; Ohleyer, Eric. Process for the production of carboxylic acids from alcohols using Saccharomyces. U.S. (1997), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yoshida Y: [Analysis of methionine metabolism studied by the gas chromatographic determination of 3-methylthiopropionate in urine and its clinical application]. Hokkaido Igaku Zasshi. 1985 Mar;60(2):183-94. [PubMed:3997054 ]
  2. Kaji H, Niioka T, Kojima Y, Yoshida Y, Kawakami Y: Urinary 3-methylthiopropionate excretion and the effect of D- or L-methionine ingestion studied in healthy subjects. Res Commun Chem Pathol Pharmacol. 1987 Apr;56(1):101-9. [PubMed:3589145 ]

Enzymes

Enzyme Details
1. 1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase
General function:
Involved in metal ion binding
Specific function:
Catalyzes the formation of formate and 2-keto-4-methylthiobutyrate (KMTB) from 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene). Also down-regulates cell migration mediated by MMP14. Necessary for hepatitis C virus replication in an otherwise non-permissive cell line.
Gene Name:
ADI1
Uniprot ID:
Q9BV57
Molecular weight:
21498.23
Reactions
1,2-Dihydroxy-3-keto-5-methylthiopentene + Oxygen → 3-Methylthiopropionic acid + Formic acid + Carbon monoxidedetails