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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:Delta(9)-tetrahydrocannabinolic acid
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Accession:CHEBI:67078 term browser browse the term
Definition:A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.
Synonyms:exact_synonym: (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylic acid
 related_synonym: 9-Carboxy-delta(9)-thc;   9-Carboxy-thc;   Formula=C22H30O4;   InChI=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)/t15-,16-/m1/s1;   InChIKey=UCONUSSAWGCZMV-HZPDHXFCSA-N;   SMILES=[H][C@@]12CCC(C)=C[C@@]1([H])c1c(O)c(C(O)=O)c(CCCCC)cc1OC2(C)C
 xref: CAS:23978-85-0
 xref_mesh: MESH:C025351
 xref: MetaCyc:CPD-7169;   PMID:15190053;   PMID:16511162;   Reaxys:1397267
 cyclic_relationship: is_conjugate_acid_of CHEBI:66963


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Delta(9)-tetrahydrocannabinolic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Cnr1 cannabinoid receptor 1 multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol binds to CNR1 protein]; delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol inhibits the reaction [Colforsin results in increased activity of CNR1 protein]]; delta(9)-tetrahydrocannabinolic acid inhibits the reaction [Colforsin results in increased activity of CNR1 protein] CTD PMID:28861508 NCBI chr 5:48,408,543...48,436,099
Ensembl chr 5:48,408,574...48,435,099
JBrowse link
G Cnr2 cannabinoid receptor 2 multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol binds to CNR2 protein] CTD PMID:28861508 NCBI chr 5:148,125,222...148,151,548
Ensembl chr 5:148,125,604...148,151,548
JBrowse link
G Fosb FosB proto-oncogene, AP-1 transcription factor subunit increases expression EXP delta(9)-tetrahydrocannabinolic acid results in increased expression of FOSB protein alternative form CTD PMID:18293355 NCBI chr 1:78,954,312...78,961,492
Ensembl chr 1:78,954,115...78,961,465
JBrowse link
G Il6 interleukin 6 multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-nitropropionic acid results in increased expression of IL6 mRNA] CTD PMID:28853159 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-nitropropionic acid results in increased expression of NOS2 mRNA]; T 0070907 inhibits the reaction [delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-nitropropionic acid results in increased expression of NOS2 mRNA]] CTD PMID:28853159 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions
decreases expression
increases expression
ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [Rosiglitazone results in increased expression of PPARG mRNA]
delta(9)-tetrahydrocannabinolic acid results in decreased expression of PPARG protein
delta(9)-tetrahydrocannabinolic acid results in increased expression of PPARG mRNA
CTD PMID:28853159 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression ISO delta(9)-tetrahydrocannabinolic acid results in increased expression of PPARGC1A mRNA CTD PMID:28853159 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-nitropropionic acid results in increased expression of TNF mRNA]; T 0070907 inhibits the reaction [delta(9)-tetrahydrocannabinolic acid inhibits the reaction [3-nitropropionic acid results in increased expression of TNF mRNA]] CTD PMID:28853159 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link

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  CHEBI ontology 19821
    role 19769
      application 19481
        anti-inflammatory agent 15831
          Delta(9)-tetrahydrocannabinolic acid 8
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  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic group 18737
                              organic divalent group 18728
                                organodiyl group 18728
                                  carbonyl group 18675
                                    carbonyl compound 18675
                                      carboxylic acid 18373
                                        hydroxy carboxylic acid 3650
                                          hydroxy monocarboxylic acid 3650
                                            Delta(9)-tetrahydrocannabinolic acid 8
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