validamycin A

CHEBI:29703 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its β-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus. — 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:26191 CHEBI:26191
CHEBI:50995 CHEBI:50995
CHEBI:83745 CHEBI:83745
CHEBI:87114 CHEBI:87114

Chemical structure

Computed structure properties
Molecular formula	C20H35NO13
Charge	0
Average mass	497.494 Da
Monoisotopic mass	497.21084 Da
Source	ChEBI
InChIKey	JARYYMUOCXVXNK-CSLFJTBJSA-N

SMILES

OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1

Also called

Validacin (BRAND_NAME)— chebi
Valimon (BRAND_NAME)— chebi
(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl β-D-glucopyranoside (EXACT_SYNONYM)— chebi
(+)-validamycin A (EXACT_SYNONYM)— chebi
(1S-(1α,4α,5β,6α))-1,5,6-trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-D-chiro-inositol (EXACT_SYNONYM)— chebi
1,5,6-trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-D-chiro-inositol (EXACT_SYNONYM)— chebi
1L-(1,3,4/2,6)-2,3-dihydroxy-6-hydroxymethyl-4-((1S,4R,5S,6S)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-enylamino)cyclohexyl β-D-glucopyranoside (EXACT_SYNONYM)— chebi
D-1,5,6-trideoxy-3-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-D-chiroinositol (EXACT_SYNONYM)— chebi
T-7545-A (EXACT_SYNONYM)— chebi
Validamycin (EXACT_SYNONYM)— chebi
jinganmycin A (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

bpdb:677
cas:37248-47-8
hmdb:HMDB0036592
kegg.compound:C12112
knapsack:C00018797
metacyc.compound:VALIDAMYCIN-A
pesticides:validamycin
reaxys:5319831
wikipedia.en:Validamycin

Activity roles

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

CHEBI:24127 CHEBI:24127
CHEBI:33281 CHEBI:33281
CHEBI:35718 CHEBI:35718
CHEBI:86328 CHEBI:86328

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:29703`	validamycin A	`antibioticmech:chebi-e377d60602`	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.