Showing Compound Card for 3-Isopropylmalic acid (CDB005000)

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Record Information
Version1.0
Created at2020-04-17 18:59:00 UTC
Updated at2020-12-07 19:11:25 UTC
CannabisDB IDCDB005000
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Isopropylmalic acid
Description3-Isopropylmalate, also known as IPM, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 3-Isopropylmalate is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Isopropylmalic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3S)-2-Hydroxy-3-isopropylsuccinic acidChEBI
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoic acidChEBI
2-D-Threo-hydroxy-3-carboxy-isocaproateChEBI
2-D-Threo-hydroxy-3-carboxyisocaproic acidChEBI
3-Carboxy-2-hydroxy-4-methylpentanoateChEBI
3-IsopropylmalateChEBI
(2R,3S)-2-Hydroxy-3-isopropylsuccinateGenerator
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoateGenerator
2-D-Threo-hydroxy-3-carboxy-isocaproic acidGenerator
2-D-Threo-hydroxy-3-carboxyisocaproateGenerator
3-Carboxy-2-hydroxy-4-methylpentanoic acidGenerator
3-Isopropylmalic acidGenerator
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioateHMDB
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioic acidHMDB
(2R,3S)-3-IsopropylmalateHMDB
(2R,3S)-3-Isopropylmalic acidHMDB
3-3-Isopropylmalic acidHMDB
IPMHMDB
beta-Isopropylmalate, erythro-(L)-isomerMeSH, HMDB
beta-IsopropylmalateMeSH, HMDB
(2R,3S)-2-Hydroxy-3-(1-methylethyl)butanedioic acidHMDB
2-Hydroxy-3-(1-methylethyl)butanedioic acidHMDB
IsopropylmalateHMDB
Isopropylmalic acidHMDB
beta-Isopropylmalic acidHMDB
β-Isopropylmalic acidHMDB
Chemical FormulaC7H12O5
Average Molecular Weight176.17
Monoisotopic Molecular Weight176.0685
IUPAC Name(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
Traditional Name(2R,3S)-3-isopropylmalic acid
CAS Registry Number126576-14-5
SMILES
CC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)/t4-,5+/m0/s1
InChI KeyRNQHMTFBUSSBJQ-CRCLSJGQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.28ALOGPS
logP0.16ChemAxon
logS-0.33ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.6 m³·mol⁻¹ChemAxon
Polarizability16.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Isopropylmalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-4ec856cc4eb69ab95cccSpectrum
GC-MS3-Isopropylmalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-4ec856cc4eb69ab95cccSpectrum
Predicted GC-MS3-Isopropylmalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9400000000-a5c729805d94db1fb7b3Spectrum
Predicted GC-MS3-Isopropylmalic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00bl-9135000000-1982df651c1931669daeSpectrum
Predicted GC-MS3-Isopropylmalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-1900000000-224a91a676e183e743332015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06sl-7900000000-b06817c1e6edcae6d4252015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9300000000-479bb2145817abc0bf1a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1900000000-acde792ba60cae65a2162015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0far-9700000000-cf8f9dd2b32cfd503f422015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9100000000-138111afc561c6d0a2ec2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ei-3900000000-99922dc6120c0bc9d5ac2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9300000000-6c8d0a906ce3776c47692021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-229b51add43b0209aa102021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-bcc925b37cd5d5f31b5a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q0-7900000000-222a48c445cf7526d6e62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-9100000000-6003ddbcaf34c522b89a2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012156
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028813
KNApSAcK IDC00019691
Chemspider ID4575349
KEGG Compound IDC04411
BioCyc ID2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE
BiGG IDNot Available
Wikipedia LinkIsopropylmalic acid
METLIN IDNot Available
PubChem Compound5462261
PDB IDIPM
ChEBI ID43468
References
General ReferencesNot Available