(-)-antofine (CHEBI:143911)

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CHEBI:143911 - (−)-antofine

ChEBI ID	CHEBI:143911
ChEBI Name	(−)-antofine
Stars
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.
Last Modified	21 June 2019
Submitter	rnash
Downloads	Molfile

Formula	C23H25NO3
Net Charge	0
Average Mass	363.457
Monoisotopic Mass	363.18344
SMILES	[H][C@]12CCCN1Cc1c(c3cc(OC)c(OC)cc3c3cc(OC)ccc13)C2
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

Species of Metabolite	Component	Source
Cynanchum vincetoxicum (ncbitaxon:141524)	-	PubMed (12350151)
Cryptocarya phyllostemon (IPNI:895989-1)	-	DOI (10.1071/CH9892243)
Vincetoxicum rossicum (ncbitaxon:429301)	-	PubMed (21739223)
Vincetoxicum nigrum (ncbitaxon:63502)	-	PubMed (21739223)

Roles Classification

Biological Roles:

antiviral agent A substance that destroys or inhibits replication of viruses.

phytotoxin Any toxin produced by a plant.

plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Applications:

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.

anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology

Outgoing Relation(s)
	(−)-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	Source
(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine	SUBMITTER
2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline	SUBMITTER
(−)-antofine	KNApSAcK
(R)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline	ChEBI
2,3,6-trimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene	ChEBI
(R)-antofine	ChEBI

Manual Xrefs	Databases
C00035244	KNApSAcK

Registry Numbers	Sources
CAS:32671-82-2	KNApSAcK

Citations