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=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

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 8504
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 8583	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 8583	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 8583	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.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP19A1 429 CYP2C19 2057

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135430323#section=BioAssay-Results Page: 37.0	inconclusive [Activation 6.7412 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135430323#section=BioAssay-Results Page: 39.0	inconclusive [Activation 7.5637 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135430323#section=BioAssay-Results Page: 90.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135430323#section=BioAssay-Results Page: 139.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135430323#section=BioAssay-Results Page: 138.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135430323#section=BioAssay-Results Page: 134.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135430323#section=BioAssay-Results Page: 138.0

PubMed

Title	Date	PubMed
Aminomethylation of heliomycin: Preparation and anticancer characterization of the first series of semi-synthetic derivatives.	2018-01-01	29137865
Phylum-specific regulation of resistomycin production in a Streptomyces sp. via microbial coculture.	2015-03-27	25537064
Interaction studies of resistomycin from Streptomyces aurantiacus AAA5 with calf thymus DNA and bovine serum albumin.	2012-04	22285949
Assessment of resistomycin, as an anticancer compound isolated and characterized from Streptomyces aurantiacus AAA5.	2011-12	22203554
Orchestration of discoid polyketide cyclization in the resistomycin pathway.	2008-07-02	18533655
The boat-shaped polyketide resistoflavin results from re-facial central hydroxylation of the discoid metabolite resistomycin.	2006-11-15	17090047
3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity.	1994-02	8150707

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 `Mon Mar 31 17:58:47 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:47 GMT 2025`
Record UNII	7N3A092A5X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HELIOMYCIN

Official Name

English

RESISTOMYCIN

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C258