CHROMOMYCIN A3

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C57H82O26
Molecular Weight	1183.2454
Optical Activity	UNSPECIFIED
Defined Stereocenters	25 / 25
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@@H]([C@@H]1CC2=C(C(=O)[C@H]1O[C@H]3C[C@@H](O[C@H]4C[C@@H](O[C@H]5C[C@](C)(O)[C@@H](OC(C)=O)[C@H](C)O5)[C@H](O)[C@@H](C)O4)[C@H](O)[C@@H](C)O3)C(O)=C6C(C=C(O[C@H]7C[C@@H](O[C@@H]8C[C@@H](O)[C@@H](OC)[C@@H](C)O8)[C@@H](OC(C)=O)[C@@H](C)O7)C(C)=C6O)=C2)C(=O)[C@@H](O)[C@@H](C)O

InChI

InChIKey=ZYVSOIYQKUDENJ-WKSBCEQHSA-N

InChI=1S/C57H82O26/c1-21-34(79-40-19-37(53(26(6)75-40)77-28(8)59)82-38-16-33(61)52(70-11)25(5)74-38)15-31-13-30-14-32(54(71-12)51(68)46(63)22(2)58)55(50(67)44(30)49(66)43(31)45(21)62)83-41-18-35(47(64)24(4)73-41)80-39-17-36(48(65)23(3)72-39)81-42-20-57(10,69)56(27(7)76-42)78-29(9)60/h13,15,22-27,32-33,35-42,46-48,52-56,58,61-66,69H,14,16-20H2,1-12H3/t22-,23-,24-,25-,26-,27+,32+,33-,35-,36-,37-,38-,39+,40+,41+,42+,46+,47-,48-,52+,53+,54+,55+,56+,57+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C57H82O26
Molecular Weight	1183.2454
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	25 / 25
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24905484

Chromomycin A3 is an anticancer antibiotic, inhibits DNA synthesis by inhibiting DNA gyrase. The antibiotic has potential reactive centers that could interact with GSH, the most abundant non-protein thiol in eukaryotic cells and a putative cofactor involved in the activation of many antibiotics in vivo. It was found, that chromomycin A3 may be potential drug leads for tumor necrosis factor (TNF)-related apoptosis-inducing ligand, TRAIL-resistant and Wnt signal-related diseases and will be useful chemical tools for use in investigating TRAIL and the Wnt signaling pathway.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase 1 Target ID: DNA gyrase Sources: https://www.ncbi.nlm.nih.gov/pubmed/7926028	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastric adenocarcinoma 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24905484	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Sequence-selective DNA binding drugs mithramycin A and chromomycin A3 are potent inhibitors of neuronal apoptosis induced by oxidative stress and DNA damage in cortical neurons.	2001-03	11261509

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Chromomycins A3 showed potent cytotoxicity against the human gastric adenocarcinoma (AGS) cell line (IC50 22.1 nM), as well as strong inhibitory effects against TCF/β-catenin transcription (IC50 15.9 nM). Chromomycins A3 showed the ability to overcome tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) resistance.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:54 GMT 2025`
Record UNII	DVW027E7NL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-58514

Preferred Name

English

CHROMOMYCIN A3

Common Name

English

ABURAMYCIN B

Common Name

English

CHROMOMYCIN A3 [MI]

Common Name

English

CHROMOMYCIN A3 [JAN]

Common Name

English

TOYOMYCIN

Common Name

English

OLIVOMYCIN D, 3D-O-(4-O-ACETYL-2,6-DIDEOXY-3-C-METHYL-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)-7-METHYL-

Common Name

English

Chromomycin a3 [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C371