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

[H][C@]1(C[C@@H](O)[C@@H](OC)[C@@H](C)O1)O[C@@H]2C[C@H](OC3=C(C)C(O)=C4C(C=C5C[C@@]([H])([C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H](O[C@@]6([H])C[C@@H](O[C@@]7([H])C[C@@H](O[C@@]8([H])C[C@](C)(O)[C@@H](OC(C)=O)[C@H](C)O8)[C@H](O)[C@@H](C)O7)[C@H](O)[C@@H](C)O6)C(=O)C5=C4O)=C3)O[C@H](C)[C@@H]2OC(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 8297

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 Mar	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 `Fri Dec 15 15:34:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:34:57 GMT 2023`
Record UNII	DVW027E7NL
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CHROMOMYCIN A3

Common Name

English

ABURAMYCIN B

Common Name

English

NSC-58514

Code

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