3-(Z)-caffeoyllupeol

CHEBI:65549 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A pentacyclic triterpenoid that is the cinnamate ester obtained by the formal condensation of the carboxylic group of cis-caffeic acid with the hydroxy group of lupeol (the 3β stereoisomer). It is isolated from the fruits of Bruguiera parviflora and exhibits antimalarial 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:25872 CHEBI:25872
CHEBI:33566 CHEBI:33566
CHEBI:36087 CHEBI:36087

Chemical structure

Computed structure properties
Molecular formula	C39H56O4
Charge	0
Average mass	588.873 Da
Monoisotopic mass	588.41786 Da
Source	ChEBI
InChIKey	NIKLINODNHPPMX-JPXCXHODSA-N

SMILES

[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](OC(=O)/C=C\c3ccc(O)c(O)c3)CC[C@]21C

InChI

InChI=1S/C39H56O4/c1-24(2)26-15-18-36(5)21-22-38(7)27(34(26)36)11-13-31-37(6)19-17-32(35(3,4)30(37)16-20-39(31,38)8)43-33(42)14-10-25-9-12-28(40)29(41)23-25/h9-10,12,14,23,26-27,30-32,34,40-41H,1,11,13,15-22H2,2-8H3/b14-10-/t26-,27+,30-,31+,32-,34+,36+,37-,38+,39+/m0/s1

Also called

(3β)-lup-20(29)-en-3-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:10050764

Activity roles

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

CHEBI:38068 CHEBI:38068

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:65549`	3-(Z)-caffeoyllupeol	`antibioticmech:chebi-d3e42a0d46`	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.