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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:06:29 UTC
Update Date2021-09-14 14:58:05 UTC
HMDB IDHMDB0060906
Secondary Accession Numbers
  • HMDB60906
Metabolite Identification
Common Name11-Hydroxy-delta-9-THC
Description11-Hydroxy-delta-9-THC, also known as 11-hydroxy-δ-9-THC, 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. 11-Hydroxy-delta-9-THC is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866121
Synonyms
ValueSource
11-Hydroxy-δ-9-THCGenerator
11-Hydroxy-delta(9)-tetrahydrocannabinolHMDB
11-Hydroxy-delta(9)-THCHMDB
11-Hydroxy-delta(9)-tetrahydrocannabinol, (6ar-trans)-isomerHMDB
11-HydroxytetrahydrocannabinolHMDB
11-Hydroxy-delta(9)-tetrahydrocannabinol, (trans)-isomerHMDB
7-Hydroxy-delta(1)-tetrahydrocannabinolHMDB
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC Name9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
Traditional Name11-Hydroxy-THC
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2C3C=C(CO)CCC3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3
InChI KeyYCBKSSAWEUDACY-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0093 g/LALOGPS
logP5.78ALOGPS
logP4.66ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.51 m³·mol⁻¹ChemAxon
Polarizability39.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+181.83231661259
DarkChem[M-H]-179.0931661259
DeepCCS[M+H]+193.49930932474
DeepCCS[M-H]-191.14130932474
DeepCCS[M-2H]-224.09430932474
DeepCCS[M+Na]+199.7430932474
AllCCS[M+H]+183.532859911
AllCCS[M+H-H2O]+180.532859911
AllCCS[M+NH4]+186.332859911
AllCCS[M+Na]+187.132859911
AllCCS[M-H]-189.232859911
AllCCS[M+Na-2H]-189.832859911
AllCCS[M+HCOO]-190.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11-Hydroxy-delta-9-THCCCCCCC1=CC(O)=C2C3C=C(CO)CCC3C(C)(C)OC2=C13606.1Standard polar33892256
11-Hydroxy-delta-9-THCCCCCCC1=CC(O)=C2C3C=C(CO)CCC3C(C)(C)OC2=C12718.5Standard non polar33892256
11-Hydroxy-delta-9-THCCCCCCC1=CC(O)=C2C3C=C(CO)CCC3C(C)(C)OC2=C12895.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11-Hydroxy-delta-9-THC,1TMS,isomer #1CCCCCC1=CC2=C(C(O[Si](C)(C)C)=C1)C1C=C(CO)CCC1C(C)(C)O22648.4Semi standard non polar33892256
11-Hydroxy-delta-9-THC,1TMS,isomer #2CCCCCC1=CC(O)=C2C(=C1)OC(C)(C)C1CCC(CO[Si](C)(C)C)=CC212644.7Semi standard non polar33892256
11-Hydroxy-delta-9-THC,2TMS,isomer #1CCCCCC1=CC2=C(C(O[Si](C)(C)C)=C1)C1C=C(CO[Si](C)(C)C)CCC1C(C)(C)O22621.3Semi standard non polar33892256
11-Hydroxy-delta-9-THC,1TBDMS,isomer #1CCCCCC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1C=C(CO)CCC1C(C)(C)O22879.0Semi standard non polar33892256
11-Hydroxy-delta-9-THC,1TBDMS,isomer #2CCCCCC1=CC(O)=C2C(=C1)OC(C)(C)C1CCC(CO[Si](C)(C)C(C)(C)C)=CC212892.8Semi standard non polar33892256
11-Hydroxy-delta-9-THC,2TBDMS,isomer #1CCCCCC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1C=C(CO[Si](C)(C)C(C)(C)C)CCC1C(C)(C)O23044.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11-Hydroxy-delta-9-THC GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pxs-5194000000-90688c2be83fa30f8ac72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Hydroxy-delta-9-THC GC-MS (2 TMS) - 70eV, Positivesplash10-05ur-5405900000-79bd0cd65b75242f99052017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Hydroxy-delta-9-THC GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Hydroxy-delta-9-THC GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 10V, Positive-QTOFsplash10-01q9-0229000000-629bcadafa0cc4dd3cdb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 20V, Positive-QTOFsplash10-0229-3393000000-df000475d1979434f7ac2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 40V, Positive-QTOFsplash10-1073-9240000000-07f27f2ea834dcffdafe2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 10V, Negative-QTOFsplash10-004i-0019000000-0f31ad0b33a131cc92c62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 20V, Negative-QTOFsplash10-004j-0359000000-ee7ca2a4145aea16ae242017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 40V, Negative-QTOFsplash10-03dr-0951000000-7a8d3325bcc5b7b782822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 10V, Positive-QTOFsplash10-001i-0009000000-c02b0dd42396d1c408db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 20V, Positive-QTOFsplash10-001i-0129000000-18b8cc8433f72c10684f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 40V, Positive-QTOFsplash10-0udi-3942000000-4477200f5235277398552021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 10V, Negative-QTOFsplash10-004i-0009000000-3acdbd949ad93c49c37e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 20V, Negative-QTOFsplash10-004i-0009000000-c6261126ba628696b19d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxy-delta-9-THC 40V, Negative-QTOFsplash10-0ar9-0191000000-402f5eabda5792af2cfa2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound37482
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available