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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 of HELIOMYCIN

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
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

Sources: DOI: 10.22259/ijrpb.0402001

Originator

Sources: DOI: 10.1007/BF00622090

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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.
Primary
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.
Curative
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

PubMed

TitleDatePubMed
Orchestration of discoid polyketide cyclization in the resistomycin pathway.
2008 Jul 2
Interaction studies of resistomycin from Streptomyces aurantiacus AAA5 with calf thymus DNA and bovine serum albumin.
2012 Apr
Patents

Patents

Sample Use Guides

Locally, 1-2 times per day for 5-7 days or more
Route of Administration: Topical
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
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
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C75147
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
PRIMARY
MESH
C007912
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
PRIMARY
CAS
20004-62-0
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
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EVMPD
SUB08013MIG
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
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ChEMBL
CHEMBL1320139
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EPA CompTox
DTXSID4046101
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PRIMARY
MERCK INDEX
m9542
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
PRIMARY Merck Index
FDA UNII
7N3A092A5X
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
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SMS_ID
100000083928
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
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INN
3053
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
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PUBCHEM
5282060
Created by admin on Fri Dec 15 15:29:17 UTC 2023 , Edited by admin on Fri Dec 15 15:29:17 UTC 2023
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