(−)-antofine

CHEBI:143911 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:22315 CHEBI:22315
CHEBI:35618 CHEBI:35618
CHEBI:38164 CHEBI:38164
CHEBI:86322 CHEBI:86322

Chemical structure

Computed structure properties
Molecular formula	C23H25NO3
Charge	0
Average mass	363.457 Da
Monoisotopic mass	363.18344 Da
Source	ChEBI
InChIKey	NCVWJDISIZHFQS-CQSZACIVSA-N

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

Also called

(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline (EXACT_SYNONYM)— chebi
(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine (EXACT_SYNONYM)— chebi
(R)-(−)-antofine (EXACT_SYNONYM)— chebi
(R)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline (EXACT_SYNONYM)— chebi
(R)-antofine (EXACT_SYNONYM)— chebi
2,3,6-trimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene (EXACT_SYNONYM)— chebi
2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline (EXACT_SYNONYM)— chebi
7-demethoxytylophorine (EXACT_SYNONYM)— chebi
9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline (EXACT_SYNONYM)— chebi
antofine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:32671-82-2
knapsack:C00035244

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:22587 CHEBI:22587
CHEBI:33281 CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:143911`	(−)-antofine	`antibioticmech:chebi-af62c3ea84`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.