ANTIMYCIN A1B

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H40N2O9
Molecular Weight	548.6252
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC[C@@H]1[C@@H](OC(=O)CC(C)C)[C@H](C)OC(=O)[C@@H](NC(=O)C2=CC=CC(NC=O)=C2O)[C@@H](C)OC1=O

InChI

InChIKey=UIFFUZWRFRDZJC-SBOOETFBSA-N

InChI=1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20-,23+,25+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H40N2O9
Molecular Weight	548.6252
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24367419 | https://www.ncbi.nlm.nih.gov/pubmed/20080599 | https://www.ncbi.nlm.nih.gov/pubmed/22442197 | https://www.ncbi.nlm.nih.gov/pubmed/22493009https://www.ncbi.nlm.nih.gov/pubmed/22339355
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8784423

Antimycin A1b acts as a novel pesticide and fungicide as well is useful in antibiotics. Antimycin A1 is an inhibitor of ACL (ATP Citrate Lyase) against the substrate citrate with promising Ki value: 29.5 uM. ACL is aberrantly expressed in many immortalized cells and tumors, such as breast, liver, colon, lung and prostate cancers, and is correlated reversely with tumor stage and differentiation, serving as a negative prognostic marker. ACL inhibitors, such as Antimycin A1, offer a new insight into their potential application in cancer treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
ATP-citrate synthase 6 Target ID: CHEMBL3720 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22339355 \| https://www.ncbi.nlm.nih.gov/pubmed/9360616	Inhibitor 8297	29.5 µM [Ki]
Saccharomyces cerevisiae 2 Target ID: CHEMBL361 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8784423	Inhibitor 8297
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8784423	Inhibitor 8297
Mucor mucedo 1 Target ID: CHEMBL613767 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8784423	Inhibitor 8297
Pneumocystis carinii 4 Target ID: CHEMBL613064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7726490	Inhibitor 8297
Apoptosis regulator Bcl-2 19 Target ID: P10415 Gene ID: 596.0 Gene Symbol: BCL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11175751	Inhibitor 8297
Bcl-2-like protein 1 3 Target ID: Q07817 Gene ID: 598.0 Gene Symbol: BCL2L1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11175751	Inhibitor 8297
Cytochrome b-c1 complex subunit 7 1 Target ID: CHEMBL1671612 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20080599 \| https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3225892/	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22339355	Primary		Basic research	Unknown Approved Use Unknown
Unknown 2578

PubMed

Title	Date	PubMed
A plasma signature of human mitochondrial disease revealed through metabolic profiling of spent media from cultured muscle cells.	2010 Jan 26	20080599
Mitochondrial reactive oxygen species and calcium uptake regulate activation of phagocytic NADPH oxidase.	2012 May 15	22442197
The regulation and biosynthesis of antimycins.	2013 Nov 19	24367419

Patents

Sample Use Guides

In Vivo Use Guide

Antimycin A LD50 was 28 mg/kg in rat

Route of Administration: Oral

In Vitro Use Guide

The effect of mitochondrial inhibitor antimycin on PMA-dependent activation of phagocytic NADPH oxidase was studied in human lymphoblasts. Lymphoblasts were treated with NADPH oxidase activator PMA or stimulator of mitochondrial O2− antimycin A (10 uM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:22:03 GMT 2023` Edited by `admin` on `Sat Dec 16 10:22:03 GMT 2023`
Record UNII	75G3NMU1TS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANTIMYCIN A1B

Common Name

English

BUTANOIC ACID, 3-METHYL-, 3-((3-(FORMYLAMINO)-2-HYDROXYBENZOYL)AMINO)-8-HEXYL-2,6-DIMETHYL-4,9-DIOXO-1,5-DIOXONAN-7-YL ESTER, (2R-(2R*,3S*,6S*,7R*,8R*))-

Systematic Name

English

BUTANOIC ACID, 3-METHYL-, (2R,3S,6S,7R,8R)-3-((3-(FORMYLAMINO)-2-HYDROXYBENZOYL)AMINO)-8-HEXYL-2,6-DIMETHYL-4,9-DIOXO-1,5-DIOXONAN-7-YL ESTER

Common Name

English

Code System Code Type Description

CHEBI

2762

Created by admin on Sat Dec 16 10:22:03 GMT 2023 , Edited by admin on Sat Dec 16 10:22:03 GMT 2023

PRIMARY

CAS

116095-18-2

Created by admin on Sat Dec 16 10:22:03 GMT 2023 , Edited by admin on Sat Dec 16 10:22:03 GMT 2023

PRIMARY

PUBCHEM

14957

Created by admin on Sat Dec 16 10:22:03 GMT 2023 , Edited by admin on Sat Dec 16 10:22:03 GMT 2023

PRIMARY

FDA UNII

75G3NMU1TS

Created by admin on Sat Dec 16 10:22:03 GMT 2023 , Edited by admin on Sat Dec 16 10:22:03 GMT 2023

PRIMARY

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					75G3NMU1TS

ANTIMYCIN A1B

ACTIVE MOIETY

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

PubMed

Patents

Sample Use Guides