PICROMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H47NO8
Molecular Weight	525.6747
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]2(O[C@H]1[C@@H](C)C[C@@H](C)C(=O)\C=C\[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)C(=O)[C@@H]1C)O[C@H](C)C[C@@H]([C@H]2O)N(C)C

InChI

InChIKey=UZQBOFAUUTZOQE-VSLWXVDYSA-N

InChI=1S/C28H47NO8/c1-10-22-28(7,34)12-11-21(30)15(2)13-16(3)25(18(5)23(31)19(6)26(33)36-22)37-27-24(32)20(29(8)9)14-17(4)35-27/h11-12,15-20,22,24-25,27,32,34H,10,13-14H2,1-9H3/b12-11+/t15-,16+,17-,18+,19-,20+,22-,24-,25+,27+,28+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H47NO8
Molecular Weight	525.6747
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13123945
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19027305 | https://www.ncbi.nlm.nih.gov/pubmed/14353806

Picromycin was studied by Brokmann and Hekel in 1951 and was the first antibiotic macrolide to be isolated. Picromycin is not a clinically useful antibiotic, it can be used as a raw material to synthesize antibiotic ketolide compounds such as ertythromycins and new epothilones. Picromycin is an antibiotic active mainly against gram-positive bacteria.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Streptococcus pneumoniae 25 Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13123945	Inhibitor 8297
Streptococcus pyogenes 6 Target ID: CHEMBL356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13123945	Inhibitor 8297
Mycobacterium tuberculosis 21 Target ID: CHEMBL360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13123945	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gram-positive bacterial infections 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13123945 https://www.ncbi.nlm.nih.gov/pubmed/14353806	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antibiotic properties of picromycin.	1953	13123945
The methymycin/pikromycin pathway: a model for metabolic diversity in natural product biosynthesis.	2009 Mar 15	19027305

Patents

Sample Use Guides

In Vivo Use Guide

50 mg/kg daily for 7 days

Route of Administration: Other

In Vitro Use Guide

Picromycin weakly inhibited Streptococcus pneumoniae with MIC 0.1 ug/ml

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:08:03 GMT 2023` Edited by `admin` on `Sat Dec 16 10:08:03 GMT 2023`
Record UNII	FBM8G3Z439
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PICROMYCIN

Common Name

English

ALBOMYCETIN

Common Name

English

OXACYCLOTETRADEC-11-ENE-2,4,10-TRIONE, 14-ETHYL-13-HYDROXY-3,5,7,9,13-PENTAMETHYL-6-((3,4,6-TRIDEOXY-3-(DIMETHYLAMINO)-.BETA.-D-XYLO-HEXOPYRANOSYL)OXY)-, (3R,5R,6S,7S,9R,11E,13S,14R)-

Systematic Name

English

ANTIBIOTIC B-62169A

Code

English

PICROMYCIN [MI]

Common Name

English

(3R-(3R*,5R*,6S*,7S*,9R*,11E,13S*,14R*))-14-ETHYL-13-HYDROXY-3,5,7,9,13-PENTAMETHYL-6-((3,4,6-TRIDEOXY-3-(DIMETHYLAMINO)-.BETA.-D-XYLO-HEXOPYRANOSYL)OXY)OXACYCLOTETRADEC-11-ENE-2,4,10-TRIONE

Systematic Name

English

AMAROMYCIN

Common Name

English

Code System Code Type Description

MERCK INDEX

m8795