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Record Information
Version3.6
Creation Date2013-07-09 16:06:39 UTC
Update Date2016-02-11 08:15:14 UTC
HMDB IDHMDB60909
Secondary Accession NumbersNone
Metabolite Identification
Common Name7-alpha-Hydroxy-delta-9-THC
Description7-alpha-Hydroxy-delta-9-THC is a metabolite of dronabinol. Dronabinol is the for a pure isomer of THC, (–)-trans-Δ9-tetrahydrocannabinol, which is the main isomer found in cannabis. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC Name(7S)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-1,7-diol
Traditional Name(7S)-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-1,7-diol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2C3C=C(C)C[C@@H](O)C3C(C)(C)OC2=C1
InChI Identifier
InChI=1/C21H30O3/c1-5-6-7-8-14-11-16(22)19-15-9-13(2)10-17(23)20(15)21(3,4)24-18(19)12-14/h9,11-12,15,17,20,22-23H,5-8,10H2,1-4H3/t15?,17-,20?/s2
InChI KeyInChIKey=DJCKLUPKZRLTPE-IWPGQCKBNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • Alkyl aryl ether
  • Benzenoid
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.018 mg/mLALOGPS
logP5.32ALOGPS
logP4.6ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.3 m3·mol-1ChemAxon
Polarizability39.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00123
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60909
Metagene LinkHMDB60909
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available