Showing Compound Card for 1,2-Dihydroxy-3-keto-5-methylthiopentene (CDB004996)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:58:35 UTC
Updated at2020-11-18 16:39:11 UTC
CannabisDB IDCDB004996
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,2-Dihydroxy-3-keto-5-methylthiopentene
Description1,2-Dihydroxy-3-keto-5-methylthiopentene, also known as 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one or acireductone, belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom. 1,2-Dihydroxy-3-keto-5-methylthiopentene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-Dihydroxy-3-keto-5-methylthiopentene exists in all living species, ranging from bacteria to humans. Outside of the human body, 1,2-Dihydroxy-3-keto-5-methylthiopentene has been detected, but not quantified in, several different foods, such as nopals, chayotes, mustard spinachs, pigeon pea, and red bell peppers. This could make 1,2-dihydroxy-3-keto-5-methylthiopentene a potential biomarker for the consumption of these foods. 1,2-Dihydroxy-3-keto-5-methylthiopentene is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneChEBI
1,2-Dihydroxy-5-(methylsulphanyl)pent-1-en-3-oneGenerator
AcireductoneChEBI, HMDB
1,2-Dihydroxy-3-keto-5-methylthiopentaneHMDB
1,2-Dihydroxy-3-keto-5-methylthiopentene anionHMDB
1,2-Dihydroxy-5-(methylthio)pent-1-en-3-oneHMDB
Chemical FormulaC6H10O3S
Average Molecular Weight162.21
Monoisotopic Molecular Weight162.0351
IUPAC Name(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
Traditional Name(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
CAS Registry Number746507-19-7
SMILES
CSCCC(=O)C(\O)=C\O
InChI Identifier
InChI=1S/C6H10O3S/c1-10-3-2-5(8)6(9)4-7/h4,7,9H,2-3H2,1H3/b6-4-
InChI KeyCILXJJLQPTUUSS-XQRVVYSFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-branched alpha,beta-unsaturated ketones
Alternative Parents
Substituents
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Vinylogous acid
  • Enone
  • Alpha-hydroxy ketone
  • Acryloyl-group
  • Ketone
  • Enediol
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.07ALOGPS
logP0.81ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.87 m³·mol⁻¹ChemAxon
Polarizability16.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-9300000000-19a09fc38a4607410081Spectrum
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-025c-9170000000-6b6fd50d76488524c888Spectrum
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2-Dihydroxy-3-keto-5-methylthiopentene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-523c47d24f3c45c4f2852016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07xs-9700000000-cbbc0baabd68adaf65ad2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c591ef1f6d20bddce5252016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000000-bd31c9d726fbcfa6d7e12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-4d0c04f4b382ef0d5b9c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-96c889c8c6acb6410bf62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-7900000000-4e7dffabd3e521b59a332021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bta-9000000000-4dee6c63f979437272b02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-9000000000-e4050047631669464d942021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9100000000-6f5f734e698f1dbf5d5c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Enolase-phosphatase E1ENOPH14q21.22Q9UHY7 details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenaseADI12p25.3Q9BV57 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Enolase-phosphatase E1ENOPH14q21.22Q9UHY7 details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenaseADI12p25.3Q9BV57 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012134
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028796
KNApSAcK IDNot Available
Chemspider ID4575316
KEGG Compound IDC15606
BioCyc IDCPD-85
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462190
PDB IDNot Available
ChEBI ID49252
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Enolase-phosphatase E1
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the enolization of 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P) into the intermediate 2-hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (HK-MTPenyl-1-P), which is then dephosphorylated to form the acireductone 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene).
Gene Name:
ENOPH1
Uniprot ID:
Q9UHY7
Molecular weight:
28932.44
Enzyme Details
2. 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