U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H16O6
Molecular Weight 376.3588
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HELIOMYCIN

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C5=C2C1=C(O)C=C5C(C)(C)C4=O

InChI

InChIKey=ABLACSIRCKEUOB-UHFFFAOYSA-N
InChI=1S/C22H16O6/c1-7-4-9(23)15-18-13(7)10(24)5-8-14(18)19-16(20(15)27)11(25)6-12(26)17(19)21(28)22(8,2)3/h4-6,23-26H,1-3H3

HIDE SMILES / InChI

Description

Heliomycin was isolated as a stable polyketide antibiotic substance produced by Streptomyces resistomycificus. Heliomycin has been shown to demonstrate antibacterial activity against gram-positive bacteria and mycobacteria. Heliomycin preferentially inhibits RNA synthesis in comparison to DNA and protein synthesis in intact bacterial cells. Heliomycin is indicated for the treatment of various dermatological pathologies, including pyoderma, pemphigus or pemphigus of newborns, trophic ulcers infected secondarily, microbial eczema, cracked nipples in women breastfeeding a baby, pseudofurunculosis and others. Since heliomycin is low in toxicity, the only contraindication is increased individual intolerance to the components of the ointment. It is cytotoxic to gastric adenocarcinoma HMO2 cells and hepatic carcinoma HePG2 cells.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity.
1994 Feb
The boat-shaped polyketide resistoflavin results from re-facial central hydroxylation of the discoid metabolite resistomycin.
2006 Nov 15
Orchestration of discoid polyketide cyclization in the resistomycin pathway.
2008 Jul 2
Assessment of resistomycin, as an anticancer compound isolated and characterized from Streptomyces aurantiacus AAA5.
2011 Dec
Interaction studies of resistomycin from Streptomyces aurantiacus AAA5 with calf thymus DNA and bovine serum albumin.
2012 Apr
Phylum-specific regulation of resistomycin production in a Streptomyces sp. via microbial coculture.
2015 Mar 27
Aminomethylation of heliomycin: Preparation and anticancer characterization of the first series of semi-synthetic derivatives.
2018 Jan 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Locally, 1-2 times per day for 5-7 days or more
Route of Administration: Topical
In Vitro Use Guide
Resistomycin inhibited apoptosis induced by actinomycin D (AD) with or without acceleration by colcemid (CL) in human megakaryoblastic leukemia CMK-7 cells, IC50 for inhibition against AD-induced apoptosis was about 0.5 uM and IC50 for inhibition against AD plus CL-induced apoptosis was about 1 uM.
Name Type Language
HELIOMYCIN
INN  
INN  
Official Name English
HELIOMYCIN [INN]
Common Name English
RESISTOMYCIN [MI]
Common Name English
ITAMYCIN
Common Name English
X-340
Common Name English
GELIOMYCIN
Code English
3,5,7,10-TETRAHYDROXY-1,1,9-TRIMETHYL-2H-BENZO(CF)PYRENE-2,6(1H)-DIONE
Systematic Name English
ANTIBIOTIC A-3733A
Code English
RESISTOMYCIN
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C75147
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY
MESH
C007912
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY
CAS
20004-62-0
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY
EVMPD
SUB08013MIG
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY
ChEMBL
CHEMBL1320139
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY
EPA CompTox
20004-62-0
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY
MERCK INDEX
M9542
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY Merck Index
INN
3053
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY
PUBCHEM
5282060
Created by admin on Tue Oct 22 06:14:31 UTC 2019 , Edited by admin on Tue Oct 22 06:14:31 UTC 2019
PRIMARY