2-O-E-p-coumaroyl alphitolic acid

CHEBI:65662 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A pentacyclic triterpenoid that is lup-20(29)-en-28-oic acid substituted by a hydroxy group at position 3 and a [(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy group at position 2 (the 2α,3β-stereoisomer ). It has been isolated from the root bark of Zizyphus jujuba and Ziziphus cambodianus. — 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:35868 CHEBI:35868
CHEBI:36087 CHEBI:36087

Chemical structure

Computed structure properties
Molecular formula	C39H54O6
Charge	0
Average mass	618.855 Da
Monoisotopic mass	618.39204 Da
Source	ChEBI
InChIKey	LCHMSLHVXVQJDG-GLDUGTPFSA-N

SMILES

[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)[C@H](OC(=O)/C=C/c3ccc(O)cc3)C[C@]21C

InChI

InChI=1S/C39H54O6/c1-23(2)26-16-19-39(34(43)44)21-20-37(6)27(32(26)39)13-14-30-36(5)22-28(33(42)35(3,4)29(36)17-18-38(30,37)7)45-31(41)15-10-24-8-11-25(40)12-9-24/h8-12,15,26-30,32-33,40,42H,1,13-14,16-22H2,2-7H3,(H,43,44)/b15-10+/t26-,27+,28+,29-,30+,32+,33-,36-,37+,38+,39-/m0/s1

Also called

(2α,3β)-3-hydroxy-2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}lup-20(29)-en-28-oic acid (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:10410488

Activity roles

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

CHEBI:64915 CHEBI:64915

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:65662`	2-O-E-p-coumaroyl alphitolic acid	`antibioticmech:chebi-caf54041e9`	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.