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The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at The data is made available under the Creative Commons License (CC 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.

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Accession:CHEBI:143911 term browser browse the term
Definition:An organic heteropentacyclic compound that is (13aR)-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. It is an alkaloid produced by relatives of the milkweed family and exhibits antiviral, anti-inflammatory, antiadipogenic and antitumorigenic activities.
Synonyms:exact_synonym: (13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
 related_synonym: (13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine;   (R)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline;   (R)-antofine;   2,3,6-trimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene;   2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline;   7-demethoxytylophorine;   9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline;   Formula=C23H25NO3;   InChI=1S/C23H25NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3/t14-/m1/s1;   InChIKey=NCVWJDISIZHFQS-CQSZACIVSA-N;   SMILES=C=1C2=C(C=C(C1OC)OC)C=3C=C(C=CC3C4=C2C[C@]5(CCCN5C4)[H])OC
 xref: CAS:32671-82-2;   KNApSAcK:C00035244
 xref_mesh: MESH:C473343
 xref: PMID:12350151;   PMID:12868894;   PMID:17049857;   PMID:20151387;   PMID:21739223;   PMID:22753104;   PMID:22880628;   PMID:24934681;   PMID:28666888;   PMID:28805975;   PMID:30691129;   PMID:31186319

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Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A decreases expression ISO antofine results in decreased expression of ABCB1 mRNA; antofine results in decreased expression of ABCB1 protein CTD PMID:22120505 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
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G Gja1 gap junction protein, alpha 1 multiple interactions
decreases expression
EXP 1,2-bis(2-aminophenoxy)ethane N,N,N',N'-tetraacetic acid acetoxymethyl ester inhibits the reaction [antofine results in decreased expression of GJA1 protein]; Ammonium Chloride inhibits the reaction [antofine results in decreased expression of GJA1 protein]; benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [antofine results in decreased expression of GJA1 protein] CTD PMID:23403203 NCBI chr20:35,756,007...35,768,481
Ensembl chr20:35,755,991...35,768,582
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  CHEBI ontology 19821
    role 19769
      biological role 19769
        antimicrobial agent 17408
          (-)-antofine 2
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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
                            heteroorganic entity 19294
                              organochalcogen compound 19064
                                organooxygen compound 19014
                                  ether 16919
                                    aromatic ether 16226
                                      (-)-antofine 2
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