Record Information
Version1.0
Creation date2015-05-07 21:33:06 UTC
Update date2018-01-25 19:56:12 UTC
Primary IDFDB031309
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameΔ9-tetrahydrocannabinolate
DescriptionΔ9-tetrahydrocannabinolate is also known as thca or δ9-tetrahydrocannabinolic acid. Δ9-tetrahydrocannabinolate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Δ9-tetrahydrocannabinolate can be found in a number of food items such as devilfish, arrowhead, potato, and cereals and cereal products, which makes Δ9-tetrahydrocannabinolate a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylic acidMetaCyc
THCAMetaCyc
Δ9-tetrahydrocannabinolic acidMetaCyc
1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylateGenerator
(6Ar)-2-carboxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-olic acidGenerator
Δ9-tetrahydrocannabinolateGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP4.47ALOGPS
logP6.25ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.54 m³·mol⁻¹ChemAxon
Polarizability41.08 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H29O4
IUPAC name(6aR)-2-carboxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-olate
InChI IdentifierInChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/p-1/t15?,16-/m1/s1
InChI KeyUCONUSSAWGCZMV-OEMAIJDKSA-M
Isomeric SMILES[H][C@@]12CCC(C)=CC1([H])C1=C(OC2(C)C)C=C(CCCCC)C(C(O)=O)=C1[O-]
Average Molecular Weight357.471
Monoisotopic Molecular Weight357.207132994
Classification
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
  • Phenoxide
  • Alkyl aryl ether
  • Benzenoid
  • Vinylogous acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organic anion
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference