HELIOMYCIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H16O6
Molecular Weight	376.3588
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C2C(O)=CC3=C4C2=C(C(O)=C1)C(=O)C5=C4C(=C(O)C=C5O)C(=O)C3(C)C

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

Molecular Formula	C22H16O6
Molecular Weight	376.3588
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/812270 | https://www.rlsnet.ru/mnn_index_id_128.htm | DOI: 10.22259/ijrpb.0402001

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA-directed RNA polymerase 11 Target ID: CHEMBL2364672 Sources: https://www.ncbi.nlm.nih.gov/pubmed/345959 \| https://www.ncbi.nlm.nih.gov/pubmed/812270	Inhibitor 8297
DNA polymerase (bacterial) 1 Target ID: DNA polymerase (bacterial) Sources: https://www.ncbi.nlm.nih.gov/pubmed/812270	Interacts 323

Conditions

Condition	Modality	Highest Phase	Product
Pyoderma 4 Sources: https://www.rlsnet.ru/mnn_index_id_128.htm	Curative	Approved 8429	Heliomycin Approved Use Indicated for the treatment of pyoderma, infected eczema, ulcers, pressure sores, varicose trophic ulcers, cracks (especially in the nipple area of nursing mothers), pemphigus of newborns, rhinitis.
Eczema 46 Sources: https://www.rlsnet.ru/mnn_index_id_128.htm https://www.ncbi.nlm.nih.gov/pubmed/4463876	Primary	Approved 8429	Heliomycin Approved Use Indicated for the treatment of pyoderma, infected eczema, ulcers, pressure sores, varicose trophic ulcers, cracks (especially in the nipple area of nursing mothers), pemphigus of newborns, rhinitis.
Infected skin diseases 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4463876 https://www.ncbi.nlm.nih.gov/pubmed/13989335	Curative	Approved 8429	Heliomycin Approved Use Indicated for the treatment of pyoderma, infected eczema, ulcers, pressure sores, varicose trophic ulcers, cracks (especially in the nipple area of nursing mothers), pemphigus of newborns, rhinitis.

PubMed

Title	Date	PubMed
3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity.	1994 Feb	8150707
The boat-shaped polyketide resistoflavin results from re-facial central hydroxylation of the discoid metabolite resistomycin.	2006 Nov 15	17090047
Orchestration of discoid polyketide cyclization in the resistomycin pathway.	2008 Jul 2	18533655
Assessment of resistomycin, as an anticancer compound isolated and characterized from Streptomyces aurantiacus AAA5.	2011 Dec	22203554
Interaction studies of resistomycin from Streptomyces aurantiacus AAA5 with calf thymus DNA and bovine serum albumin.	2012 Apr	22285949
Phylum-specific regulation of resistomycin production in a Streptomyces sp. via microbial coculture.	2015 Mar 27	25537064
Aminomethylation of heliomycin: Preparation and anticancer characterization of the first series of semi-synthetic derivatives.	2018 Jan 1	29137865

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:29:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:29:17 GMT 2023`
Record UNII	7N3A092A5X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HELIOMYCIN

Official Name

English

heliomycin [INN]

Common Name

English

RESISTOMYCIN [MI]

Common Name

English

ITAMYCIN

Common Name

English

Heliomycin [WHO-DD]

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258