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Showing metabocard for Ethanethioic acid (HMDB0031188)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:31 UTC
Update Date2023-02-21 17:19:59 UTC
HMDB IDHMDB0031188
Secondary Accession Numbers
  • HMDB31188
Metabolite Identification
Common NameEthanethioic acid
DescriptionEthanethioic acid, also known as thioacetic acid or thioacetate, belongs to the class of organic compounds known as carbothioic s-acids. These are organic acids with the general formula RCS-OH (R=H, organic group). Based on a literature review a significant number of articles have been published on Ethanethioic acid.
Structure
Data?1676999999
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031188 (Ethanethioic acid)


  Mrv0541 05061305472D          

  4  3  0  0  0  0            999 V2000
   -1.3608   -0.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033    0.5767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    0.5767    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
M  END
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3D MOL for HMDB0031188 (Ethanethioic acid)

HMDB0031188
     RDKit          3D
Ethanethioic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
   -1.0003    0.0895   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801   -0.2444    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -0.3356    1.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7253   -0.5322   -0.5475 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.8650   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    0.7833    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.5330   -1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.5714   -0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  4  8  1  0
M  END
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3D SDF for HMDB0031188 (Ethanethioic acid)


  Mrv0541 05061305472D          

  4  3  0  0  0  0            999 V2000
   -1.3608   -0.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033    0.5767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    0.5767    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031188

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(S)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4)

> <INCHI_KEY>
DUYAAUVXQSMXQP-UHFFFAOYSA-N

> <FORMULA>
C2H4OS

> <MOLECULAR_WEIGHT>
76.118

> <EXACT_MASS>
75.99828544

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
7.250941254051985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethanethioic S-acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.29016863866666653

> <ALOGPS_LOGS>
-0.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.624545717190478

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
19.0575

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
schiff reagent

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031188 (Ethanethioic acid)

HMDB0031188
     RDKit          3D
Ethanethioic acid
  8  7  0  0  0  0  0  0  0  0999 V2000
   -1.0003    0.0895   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801   -0.2444    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -0.3356    1.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7253   -0.5322   -0.5475 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.8650   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    0.7833    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.5330   -1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.5714   -0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  4  8  1  0
M  END
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PDB for HMDB0031188 (Ethanethioic acid)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.540  -1.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.540   0.309   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.926   1.077   0.000  0.00  0.00           O+0
HETATM    4  S   UNK     0      -1.308   1.077   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0031188 (Ethanethioic acid)

COMPND    HMDB0031188
HETATM    1  C1  UNL     1      -1.000   0.089  -0.192  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.280  -0.244   0.469  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.409  -0.336   1.675  1.00  0.00           O  
HETATM    4  S1  UNL     1       1.725  -0.532  -0.548  1.00  0.00           S  
HETATM    5  H1  UNL     1      -1.582  -0.865  -0.303  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.573   0.783   0.476  1.00  0.00           H  
HETATM    7  H3  UNL     1      -0.835   0.533  -1.191  1.00  0.00           H  
HETATM    8  H4  UNL     1       2.575   0.571  -0.386  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    3    4
CONECT    4    8
END
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SMILES for HMDB0031188 (Ethanethioic acid)

CC(S)=O
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INCHI for HMDB0031188 (Ethanethioic acid)

InChI=1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Acetyl mercaptanChEBI
CH3COSHChEBI
Thioacetic acidChEBI
Thioacetic S-acidChEBI
ThioacetateGenerator
EthanethioateGenerator
Ethanethioic O-acidHMDB
Ethanethiolic acidHMDB
Methanecarbothiolic acidHMDB
Schiff'S reagentHMDB
Thiacetic acidHMDB
Thio-acetic acidHMDB
Thioacetate estersHMDB
Thiolacetic acidHMDB
Thiolacetic acid?HMDB
Thionoacetic acidHMDB
Thioacetic acid, potassium saltHMDB
Thioacetic acid, sodium saltHMDB
Chemical FormulaC2H4OS
Average Molecular Weight76.118
Monoisotopic Molecular Weight75.99828544
IUPAC Nameethanethioic S-acid
Traditional Nameschiff reagent
CAS Registry Number507-09-5
SMILES
CC(S)=O
InChI Identifier
InChI=1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4)
InChI KeyDUYAAUVXQSMXQP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbothioic s-acids. These are organic acids with the general formula RCS-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarbothioic S-acids
Sub ClassNot Available
Direct ParentCarbothioic S-acids
Alternative Parents
Substituents
  • Carbothioic s-acid
  • Carbodithioic acid
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Alkylthiol
  • 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
Organoleptic effect
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point17 °CNot Available
Boiling Point88.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility101600 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.528 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.2 g/LALOGPS
logP0.78ALOGPS
logP0.29ChemAxon
logS-0.65ALOGPS
pKa (Strongest Acidic)0.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.06 m³·mol⁻¹ChemAxon
Polarizability7.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.38131661259
DarkChem[M-H]-105.09531661259
DeepCCS[M+H]+122.61330932474
DeepCCS[M-H]-120.77930932474
DeepCCS[M-2H]-156.17430932474
DeepCCS[M+Na]+130.12730932474
AllCCS[M+H]+124.032859911
AllCCS[M+H-H2O]+119.632859911
AllCCS[M+NH4]+128.132859911
AllCCS[M+Na]+129.332859911
AllCCS[M-H]-148.132859911
AllCCS[M+Na-2H]-155.032859911
AllCCS[M+HCOO]-162.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202212.971 minutes33406817
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid209.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1611.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid568.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid228.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid430.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid224.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid446.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid570.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)713.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid946.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid273.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1083.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid391.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid427.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate764.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA536.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water216.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethanethioic acidCC(S)=O1099.2Standard polar33892256
Ethanethioic acidCC(S)=O651.2Standard non polar33892256
Ethanethioic acidCC(S)=O655.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethanethioic acid,1TMS,isomer #1CC(=O)S[Si](C)(C)C860.7Semi standard non polar33892256
Ethanethioic acid,1TMS,isomer #1CC(=O)S[Si](C)(C)C868.8Standard non polar33892256
Ethanethioic acid,1TBDMS,isomer #1CC(=O)S[Si](C)(C)C(C)(C)C1101.6Semi standard non polar33892256
Ethanethioic acid,1TBDMS,isomer #1CC(=O)S[Si](C)(C)C(C)(C)C1123.4Standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003208
KNApSAcK IDNot Available
Chemspider ID10052
KEGG Compound IDC01857
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10484
PDB IDNot Available
ChEBI ID16555
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1107971
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yang W, Du DM: Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to alpha,beta-disubstituted nitroalkenes. Org Biomol Chem. 2012 Sep 14;10(34):6876-84. doi: 10.1039/c2ob26068a. Epub 2012 Jul 31. [PubMed:22847715 ]
  2. Piro B, Zhang QD, Reisberg S, Noel V, Dang LA, Duc HT, Pham MC: Direct and rapid electrochemical immunosensing system based on a conducting polymer. Talanta. 2010 Jul 15;82(2):608-12. doi: 10.1016/j.talanta.2010.05.015. Epub 2010 May 19. [PubMed:20602943 ]
  3. Liu M, Deng J, Lai C, Chen Q, Zhao Q, Zhang Y, Li H, Yao S: Synthesis, characterization of conjugated oligo-phenylene-ethynylenes and their supramolecular interaction with beta-cyclodextrin for salicylaldehyde detection. Talanta. 2012 Oct 15;100:229-38. doi: 10.1016/j.talanta.2012.08.008. Epub 2012 Aug 17. [PubMed:23141331 ]
  4. Chauhan HP, Bhatiya S: Synthesis, spectroscopic, thermal and antimicrobial studies of toluene-3,4-dithiolatoarsenic(III) derivatives with some oxygen and sulphur donor ligands. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Nov;97:1133-9. doi: 10.1016/j.saa.2012.07.086. Epub 2012 Aug 3. [PubMed:22940048 ]
  5. Inoue K, Asai N, Mizuo H, Fukuda K, Kusano K, Yoshimura T: Unique metabolic pathway of [(14)C]lenvatinib after oral administration to male cynomolgus monkey. Drug Metab Dispos. 2012 Apr;40(4):662-70. doi: 10.1124/dmd.111.043281. Epub 2011 Dec 29. [PubMed:22207053 ]
  6. Robertson F, Wu J: Convenient synthesis of allylic thioethers from phosphorothioate esters and alcohols. Org Lett. 2010 Jun 4;12(11):2668-71. doi: 10.1021/ol1009202. [PubMed:20441179 ]
  7. Fischer JA, Zoldan VC, Benitez G, Rubert AA, Ramirez EA, Carro P, Salvarezza RC, Pasa AA, Vela ME: Sulfidization of Au(111) from thioacetic acid: an experimental and theoretical study. Langmuir. 2012 Oct 30;28(43):15278-85. doi: 10.1021/la303059u. Epub 2012 Oct 18. [PubMed:23002810 ]
  8. Bendena WG, Zhang J, Burtenshaw SM, Tobe SS: Evidence for differential biosynthesis of juvenile hormone (and related) sesquiterpenoids in Drosophila melanogaster. Gen Comp Endocrinol. 2011 May 15;172(1):56-61. doi: 10.1016/j.ygcen.2011.02.014. Epub 2011 Feb 24. [PubMed:21354154 ]
  9. Cimadevilla F, Garcia ME, Garcia-Vivo D, Ruiz MA, Graiff C, Tiripicchio A: Reactions of the tetrafluoroborate complex [Mo2Cp2(kappa(2)-F2BF2)(mu-PPh2)2(CO)]BF4 with mono- and bidentate ligands having E-H bonds (E = O, S, Se, N, P). Inorg Chem. 2012 Jul 2;51(13):7284-95. doi: 10.1021/ic300626y. Epub 2012 Jun 20. [PubMed:22715993 ]
  10. Hintermann L, Turockin A: Reversible generation of metastable enols in the 1,4-addition of thioacetic acid to alpha,beta-unsaturated carbonyl compounds. J Org Chem. 2012 Dec 21;77(24):11345-8. doi: 10.1021/jo3021709. Epub 2012 Dec 3. [PubMed:23164060 ]
  11. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .