1β-hydroxymaprounic acid 3-p-hydroxybenzoate

CHEBI:66671 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pentacyclic triterpenoid that is the benzoate ester obtained by the condensation of the 3-hydroxy group of 1β-hydroxymaprounic acid with p-hydroxybenzoic acid. Isolated from Maprounea africana, it exhibits inhibitory activity against HIV-1 reverse transcriptase. — 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:36054 CHEBI:36054

Chemical structure

Computed structure properties
Molecular formula	C37H52O6
Charge	0
Average mass	592.817 Da
Monoisotopic mass	592.37639 Da
Source	ChEBI
InChIKey	VGODRAUARQJBJM-FCWPOGGHSA-N

SMILES

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

InChI

InChI=1S/C37H52O6/c1-32(2)18-19-37(31(41)42)17-14-25-34(5)15-12-24-33(3,4)29(43-30(40)22-8-10-23(38)11-9-22)20-28(39)36(24,7)26(34)13-16-35(25,6)27(37)21-32/h8-11,14,24,26-29,38-39H,12-13,15-21H2,1-7H3,(H,41,42)/t24-,26-,27-,28+,29-,34-,35+,36-,37+/m0/s1

Also called

(4aS,6bR,8aS,10S,12R,12aR,12bS,14aS,14bS)-12-hydroxy-10-[(4-hydroxybenzoyl)oxy]-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-octadecahydropicene-4a(2H)-carboxylic acid (EXACT_SYNONYM)— chebi
1-Hydroxy-3-((4-hydroxybenzoyl)oxy)-D-friedoolean-14-en-28-oic acid (1beta,3beta)- (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:155510-77-3

Activity roles

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

CHEBI:53756 CHEBI:53756

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:66671`	1β-hydroxymaprounic acid 3-p-hydroxybenzoate	`antibioticmech:chebi-6535b57018`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

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.