PLATENSIMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H27NO7
Molecular Weight	441.4737
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12C[C@]34C[C@H]1C[C@H](O2)[C@H]3[C@](C)(CCC(=O)NC5=C(O)C=CC(C(O)=O)=C5O)C(=O)C=C4

InChI

InChIKey=CSOMAHTTWTVBFL-OFBLZTNGSA-N

InChI=1S/C24H27NO7/c1-22(7-6-17(28)25-18-14(26)4-3-13(19(18)29)21(30)31)16(27)5-8-24-10-12-9-15(20(22)24)32-23(12,2)11-24/h3-5,8,12,15,20,26,29H,6-7,9-11H2,1-2H3,(H,25,28)(H,30,31)/t12-,15+,20+,22-,23+,24+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C24H27NO7
Molecular Weight	441.4737
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Concise formal total synthesis of platensimycin mediated by a stereoselective autoxidation and hydroxyl group directed conjugative reduction.	2010-12-17	21090652
A bismuth(III)-catalyzed Friedel-Crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin.	2010-12-03	21033748
An oxidative Prins-pinacol tandem process and its application to the synthesis of (-)-platensimycin.	2010-10-04	20740509
New antibiotic structures from fermentations.	2010-10	20653459
Isolation, structure and biological activities of platencin A(2)-A(4) from Streptomyces platensis.	2010-04-01	20299229
Discovery and syntheses of "superbug challengers"-platensimycin and platencin.	2010-04-01	20209576
7-Phenylplatensimycin and 11-methyl-7-phenylplatensimycin: more potent analogs of platensimycin.	2010-04-01	20207542
Novel anti-infective compounds from marine bacteria.	2010-03-05	20411112
Improvement of secondary metabolite production in Streptomyces by manipulating pathway regulation.	2010-03	20091304
Coping with antibiotic resistance: contributions from genomics.	2010-02-25	20236502
Recent advances on platensimycin: a potential antimicrobial agent.	2010	20158476
Isolation, structure and biological activities of platensimycin B4 from Streptomyces platensis.	2009-12	19911028
Total synthesis of platensimycin and related natural products.	2009-11-25	19874023
Total syntheses of (+/-)-platencin and (-)-platencin.	2009-11-04	19824676
Synthesis and biological evaluation of chromium bioorganometallics based on the antibiotic platensimycin lead structure.	2009-11	19784974
Isoplatensimycin: Synthesis and biological evaluation.	2009-08-15	19604693
Isolation, enzyme-bound structure and antibacterial activity of platencin A1 from Streptomyces platensis.	2009-08-15	19581087
An apoA-I mimetic peptide increases LCAT activity in mice through increasing HDL concentration.	2009-07-28	19680471
Platensimycin activity against mycobacterial beta-ketoacyl-ACP synthases.	2009-07-17	19609444
Stereoelectronic effect for the selectivity in C-H insertion of alkylidene carbenes and its application to the synthesis of platensimycin.	2009-06-24	19473019
Di-tert-butyl N-[2,6-bis-(methoxy-meth-oxy)phen-yl]imino-diacetate.	2009-03-25	21582540
Synthesis and biological evaluation of platensimycin analogs.	2009-03-15	19233644
From nature to the laboratory and into the clinic.	2009-03-15	19028103
Total synthesis of (-)-platensimycin, a novel antibacterial agent.	2009-02-06	19123842
A concise ring-expansion route to the compact core of platensimycin.	2009	19798708
Rhodium-catalyzed asymmetric enyne cycloisomerization of terminal alkynes and formal total synthesis of (-)-platensimycin.	2009	19606433
Efforts towards the identification of simpler platensimycin analogues--the total synthesis of oxazinidinyl platensimycin.	2009	19212990
Isolation, structure and fatty acid synthesis inhibitory activities of platensimycin B1-B3 from Streptomyces platensis.	2008-10-28	18931777
Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity.	2008-10-01	18771264
Stereocontrolled formal synthesis of (+/-)-platensimycin.	2008-09-18	18702494
A simple, efficient, and enantiocontrolled synthesis of a near-structural mimic of platensimycin.	2008-09-04	18665602
Synthesis of platensimycin analogues and their antibiotic potency.	2008-06	18442030
Structure and semisynthesis of platensimide A, produced by Streptomyces platensis.	2008-05-01	18393511
High-pressure entry into platencin.	2008	18666193
A carbonyl ylide cycloaddition approach to platensimycin.	2008	18412205
Platensimycin: a promising antimicrobial targeting fatty acid synthesis.	2008	18336284
Synthesis of platensimycin.	2008	18327757
A chiral pool based synthesis of platensimycin.	2008	18176919
Biosynthetic studies of platensimycin.	2007-12-19	18034483
Total synthesis and antibacterial properties of carbaplatensimycin.	2007-12-05	17988130
Structure-assisted discovery of an aminothiazole derivative as a lead molecule for inhibition of bacterial fatty-acid synthesis.	2007-12	18084068
An effective enantioselective route to the platensimycin core.	2007-11-08	17929829
New approaches to filling the gap in tuberculosis drug discovery.	2007-11-06	17988169
Antibacterial targets in fatty acid biosynthesis.	2007-10	17707686
Enantioselective synthesis of (-)-platensimycin oxatetracyclic core by using an intramolecular Diels-Alder reaction.	2007-09-27	17764196
Hitting bacteria at the heart of the central dogma: sequence-specific inhibition.	2007-08-10	17692125
Enantioselective route to platensimycin: an intramolecular Robinson annulation approach.	2007-08-08	17630748
Mining and engineering natural-product biosynthetic pathways.	2007-07	17576425
Formal synthesis of (+/-)-platensimycin.	2007-05-21	17695230
Protecting-group-free formal synthesis of platensimycin.	2007	17854110

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:43:40 GMT 2025` Edited by `admin` on `Mon Mar 31 22:43:40 GMT 2025`
Record UNII	Q3DQ78KOFY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PLATENSIMYCIN

Common Name

English

(-)-PLATENSIMYCIN

Preferred Name

English

3-((3-((1S,3S,4S,5AS,9S,9AR)-1,4,5,8,9,9A-HEXAHYDRO-3,9-DIMETHYL-8-OXO-3H-1,4:3,5A-DIMETHANO-2-BENZOXEPIN-9-YL)-1-OXOPROPYL)AMINO)-2,4-DIHYDROXYBENZOIC ACID

Systematic Name

English

BENZOIC ACID, 3-((3-((1S,3S,4S,5AS,9S,9AR)-1,4,5,8,9,9A-HEXAHYDRO-3,9-DIMETHYL-8-OXO-3H-1,4:3,5A-DIMETHANO-2-BENZOXEPIN-9-YL)-1-OXOPROPYL)AMINO)-2,4-DIHYDROXY-

Systematic Name

English

PLATENSIMYCIN [MI]

Common Name

English

PLATENSIMYCIN, (-)-

Common Name

English

Code System Code Type Description

PUBCHEM

6857724