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

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
Effects of atovaquone and other inhibitors on Pneumocystis carinii dihydroorotate dehydrogenase.	1995 Feb	7726490
UK-2A, B, C and D, novel antifungal antibiotics from Streptomyces sp. 517-02. I. Fermentation, isolation, and biological properties.	1996 Jul	8784423

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).

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

ACTIVE MOIETY


					75G3NMU1TS

ANTIMYCIN A1B

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

PubMed

Patents

Sample Use Guides