CHEBI:143911 - (−)-antofine

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ChEBI Name (−)-antofine
ChEBI ID CHEBI:143911
ChEBI ASCII Name (-)-antofine
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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Rob Nash
Supplier Information
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Formula C23H25NO3
Net Charge 0
Average Mass 363.457
Monoisotopic Mass 363.18344
InChI 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
Metabolite of Species Details
Cryptocarya phyllostemon (IPNI:895989-1) See: DOI
Cynanchum vincetoxicum (NCBI:txid141524) See: PubMed
Vincetoxicum rossicum (NCBI:txid429301) See: PubMed
Vincetoxicum nigrum (NCBI:txid63502) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
phytotoxin
Any toxin produced by a plant.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via alkaloid antibiotic )
antiviral agent
A substance that destroys or inhibits replication of viruses.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-antofine (CHEBI:143911) has role angiogenesis inhibitor (CHEBI:48422)
(−)-antofine (CHEBI:143911) has role anti-inflammatory agent (CHEBI:67079)
(−)-antofine (CHEBI:143911) has role antimicrobial agent (CHEBI:33281)
(−)-antofine (CHEBI:143911) has role antineoplastic agent (CHEBI:35610)
(−)-antofine (CHEBI:143911) has role antiviral agent (CHEBI:22587)
(−)-antofine (CHEBI:143911) has role phytotoxin (CHEBI:38231)
(−)-antofine (CHEBI:143911) has role plant metabolite (CHEBI:76924)
(−)-antofine (CHEBI:143911) is a alkaloid (CHEBI:22315)
(−)-antofine (CHEBI:143911) is a alkaloid antibiotic (CHEBI:86322)
(−)-antofine (CHEBI:143911) is a aromatic ether (CHEBI:35618)
(−)-antofine (CHEBI:143911) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name
(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
Synonyms Sources
(−)-antofine KNApSAcK
(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine SUBMITTER
(R)-(−)-antofine ChEBI
(R)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline ChEBI
(R)-antofine ChEBI
2,3,6-trimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene ChEBI
2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline SUBMITTER
7-demethoxytylophorine ChEBI
9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline ChEBI
antofine ChEBI
Manual Xref Database
C00035244 KNApSAcK
View more database links
Registry Number Type Source
32671-82-2 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
12350151 PubMed citation SUBMITTER
12868894 PubMed citation SUBMITTER
17049857 PubMed citation SUBMITTER
20151387 PubMed citation SUBMITTER
21739223 PubMed citation Europe PMC
22753104 PubMed citation SUBMITTER
22880628 PubMed citation SUBMITTER
24934681 PubMed citation SUBMITTER
28666888 PubMed citation Europe PMC
28805975 PubMed citation SUBMITTER
30691129 PubMed citation Europe PMC
31186319 PubMed citation Europe PMC
Last Modified
21 June 2019