benzastatin C

CHEBI:65483 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A quinoline alkaloid that is 1,2,3,4-tetrahydroquinoline-6-carboxamide substituted by a chloro group at position 3 and a 3,4-dimethylpent-3-en-1-yl and a methoxymethyl group at position 2 (the 2R,3R stereoisomer). Isolated from the culture broth of Streptomyces nitrosporeus 30643, it exhibits inhibitory potential against lipid peroxidation and anti-HSV activity. — 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:22702 CHEBI:22702
CHEBI:25698 CHEBI:25698
CHEBI:26509 CHEBI:26509
CHEBI:36683 CHEBI:36683

Chemical structure

Computed structure properties
Molecular formula	C19H27ClN2O2
Charge	0
Average mass	350.89 Da
Monoisotopic mass	350.17611 Da
Source	ChEBI
InChIKey	AHGKSZXKDPGMQU-IEBWSBKVSA-N

SMILES

COC[C@@]1(CCC(C)=C(C)C)Nc2ccc(C(N)=O)cc2C[C@H]1Cl

InChI

InChI=1S/C19H27ClN2O2/c1-12(2)13(3)7-8-19(11-24-4)17(20)10-15-9-14(18(21)23)5-6-16(15)22-19/h5-6,9,17,22H,7-8,10-11H2,1-4H3,(H2,21,23)/t17-,19-/m1/s1

Also called

(2R,3R)-3-chloro-2-(3,4-dimethylpent-3-en-1-yl)-2-(methoxymethyl)-1,2,3,4-tetrahydroquinoline-6-carboxamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:7467320

Activity roles

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

CHEBI:64952 CHEBI:64952

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:65483`	benzastatin C	`antibioticmech:chebi-b9925314ef`	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.