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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]; delta(9)-tetrahydrocannabinolic acid promotes the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol promotes the reaction [Guanosine 5'-O-(3-Thiotriphosphate) binds to CNR1 protein]]; delta(9)-tetrahydrocannabinolic acid promotes the reaction [Guanosine 5'-O-(3-Thiotriphosphate) binds to CNR1 protein] CTD PMID:28861508 PMID:32510591 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]; delta(9)-tetrahydrocannabinolic acid inhibits the reaction [Guanosine 5'-O-(3-Thiotriphosphate) binds to CNR2 protein] CTD PMID:28861508 PMID:32510591 NCBI chr 5:148,125,222...148,151,548
Ensembl chr 5:148,125,604...148,151,548
JBrowse link
G Col3a1 collagen type III alpha 1 chain multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [TGFB1 protein results in increased expression of COL3A1 mRNA] CTD PMID:33341026 NCBI chr 9:47,374,611...47,410,547
Ensembl chr 9:47,374,593...47,410,547
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 Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation
ISO Rimonabant inhibits the reaction [delta(9)-tetrahydrocannabinolic acid results in increased phosphorylation of MAPK1 protein] CTD PMID:32510591 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions
ISO delta(9)-tetrahydrocannabinolic acid results in increased phosphorylation of MAPK3 protein
Rimonabant inhibits the reaction [delta(9)-tetrahydrocannabinolic acid results in increased phosphorylation of MAPK3 protein]
CTD PMID:32510591 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
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 Tgfb1 transforming growth factor, beta 1 multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [TGFB1 protein results in increased expression of COL3A1 mRNA]; delta(9)-tetrahydrocannabinolic acid inhibits the reaction [TGFB1 protein results in increased expression of TNC mRNA] CTD PMID:33341026 NCBI chr 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847
JBrowse link
G Tnc tenascin C multiple interactions ISO delta(9)-tetrahydrocannabinolic acid inhibits the reaction [TGFB1 protein results in increased expression of TNC mRNA] CTD PMID:33341026 NCBI chr 5:77,375,851...77,460,712
Ensembl chr 5:77,375,851...77,460,624
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 20089
    role 20042
      application 19781
        anti-inflammatory agent 16481
          Delta(9)-tetrahydrocannabinolic acid 13
Path 2
Term Annotations click to browse term
  CHEBI ontology 20089
    subatomic particle 20058
      composite particle 20058
        hadron 20088
          baryon 20088
            nucleon 20088
              atomic nucleus 20088
                atom 20058
                  main group element atom 19960
                    p-block element atom 19990
                      carbon group element atom 19916
                        carbon atom 19909
                          organic molecular entity 19909
                            organic group 18988
                              organic divalent group 18950
                                organodiyl group 18974
                                  carbonyl group 18903
                                    carbonyl compound 18925
                                      carboxylic acid 18597
                                        hydroxy carboxylic acid 3728
                                          hydroxy monocarboxylic acid 3723
                                            Delta(9)-tetrahydrocannabinolic acid 13
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