2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate

CHEBI:66672 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pentacyclic triterpenoid that is the diester obtained by the condensation of the hydroxy groups of 2α-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:36054 CHEBI:36054

Chemical structure

Computed structure properties
Molecular formula	C44H56O8
Charge	0
Average mass	712.924 Da
Monoisotopic mass	712.39752 Da
Source	ChEBI
InChIKey	XPEVLOSUULAUFH-AHHVVZNJSA-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@H](OC(=O)c3ccc(O)cc3)C[C@]21C

InChI

InChI=1S/C44H56O8/c1-39(2)22-23-44(38(49)50)21-18-32-41(5)19-16-31-40(3,4)35(52-37(48)27-10-14-29(46)15-11-27)30(51-36(47)26-8-12-28(45)13-9-26)24-43(31,7)33(41)17-20-42(32,6)34(44)25-39/h8-15,18,30-31,33-35,45-46H,16-17,19-25H2,1-7H3,(H,49,50)/t30-,31+,33+,34+,35+,41+,42-,43+,44-/m1/s1

Also called

(4aS,6bR,8aR,10R,11R,12aR,12bR,14aS,14bS)-10,11-bis[(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
D-Friedoolean-14-en-28-oic acid, 1,3-bis((4-hydroxybenzoyl)oxy)-,(1beta,3beta)- (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:155510-78-4

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:66672`	2α-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate	`antibioticmech:chebi-b0f76aa431`	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.