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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H37N5O14
Molecular Weight 583.5436
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Anthelmycin

SMILES

[H][C@@](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O)([C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)[C@@]2([H])O[C@H]([C@H](O)[C@@H](O)[C@@H]2N)N3C=CC(N)=NC3=O

InChI

InChIKey=VQQSDVBOXQHCHU-SKPOXZENSA-N
InChI=1S/C21H37N5O14/c22-7-1-2-26(21(37)25-7)19-16(36)12(32)9(24)17(39-19)18(15(35)14(34)10(30)5(29)3-27)40-20-13(33)8(23)11(31)6(4-28)38-20/h1-2,5-6,8-20,27-36H,3-4,23-24H2,(H2,22,25,37)/t5-,6-,8+,9+,10-,11-,12+,13-,14+,15+,16-,17+,18-,19-,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H37N5O14
Molecular Weight 583.5436
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 0
Optical Activity UNSPECIFIED

The antibiotic anthelmycin was first isolated by Hamill and Hoehn from culture filtrates of Streptomyces longissimus. Anthelmycin (hikizimycin) has also been isolated from the fermentation broth of Streptomyces sp., strain A-5 which was obtained from a soil sample collected at the Hikizi river-side, Kanagawa Prefecture, Japan, by Uchida K. et al. Anthelmycin (hikizimycin) is active against fungi, especially phytopathogenic fungi. The drug inhibits the growth of a number of prokaryotic and eukaryotic organisms and also has antihelminthic activity. Anthelmycin inhibits protein synthesis on both pro- and eukaryotic ribosomes by preventing the peptide bond-forming reaction. The drug is structurally similar to certain other 4-aminohexosyl cytosine antibiotics including blasticidin S, gougerotin, amicetin and bamicetin although unlike these compounds anthelmycin lacks an aminoacyl moiety. It is proposed that anthelmycin inhibits the ribosomal peptidyl transferase centre by associating with a site that overlaps the (related) ribosomal receptor site(s) for the other four inhibitors.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:31:31 GMT 2023
Edited
by admin
on Sat Dec 16 04:31:31 GMT 2023
Record UNII
7PB008085S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Anthelmycin
USAN  
USAN  
Official Name English
antelmycin [INN]
Common Name English
ANTHELMYCIN [USAN]
Common Name English
NSC-337588
Code English
HIKIZIMYCIN
Common Name English
(-)-HIKIZIMYCIN
Common Name English
ANTELMYCIN
INN  
INN  
Official Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-(4-AMINO-6-O-(3-AMINO-3-DEOXY-.BETA.-D-GLUCOPYRANOSYL)-4-DEOXY-D-GLYCERO-D-GALACTO-.BETA.-D-GLUCO-UNDECOPYRANOSYL)-
Systematic Name English
Code System Code Type Description
FDA UNII
7PB008085S
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
PUBCHEM
75905628
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
NCI_THESAURUS
C171714
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
NSC
337588
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
CAS
1402-84-2
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
SUPERSEDED
CAS
12706-94-4
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
SMS_ID
300000036890
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
CHEBI
88275
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104016
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
INN
1842
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID101318176
Created by admin on Sat Dec 16 04:31:31 GMT 2023 , Edited by admin on Sat Dec 16 04:31:31 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY