N-BENZOYL-3-PHENYLISOSERINE, (2R,3S)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H15NO4
Molecular Weight	285.2946
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of N-BENZOYL-3-PHENYLISOSERINE, (2R,3S)-

SMILES

O[C@H]([C@@H](NC(=O)C1=CC=CC=C1)C2=CC=CC=C2)C(O)=O

InChI

InChIKey=HYJVYOWKYPNSTK-UONOGXRCSA-N

InChI=1S/C16H15NO4/c18-14(16(20)21)13(11-7-3-1-4-8-11)17-15(19)12-9-5-2-6-10-12/h1-10,13-14,18H,(H,17,19)(H,20,21)/t13-,14+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H15NO4
Molecular Weight	285.2946
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

(2R,3S)-N-Benzoyl-3-phenylisoserine (also known as the “taxol side chain”) is a structural component of the antimicrotubular drug paclitaxel.

Approval Year

Conditions

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2,596

PubMed

Show entries

Title	Date	PubMed
Effect of antiproliferative agents on vascular function in normal and in vitro balloon-injured porcine coronary arteries.	2003 Nov 14	14637181
Characterization of an abeo-taxane: brevifoliol and derivatives.	2004 May	15165147
Cytotoxic, antiviral (in-vitro and in-vivo), immunomodulatory activity and influence on mitotic divisions of three taxol derivatives: 10-deacetyl-baccatin III, methyl (N-benzoyl-(2'R,3'S)-3'-phenylisoserinate) and N-benzoyl-(2'R,3'S)-3'-phenylisoserine.	2005 Jun	15969936
Clinical trials and progress with paclitaxel in ovarian cancer.	2010 Nov 19	21270965
Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine.	2013 Jul 11	24900723

Showing 1 to 5 of 5 entries

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Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	D998Q2WJCM
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

N-BENZOYL-3-PHENYLISOSERINE, (2R,3S)-

Systematic Name

English

BENZENEPROPANOIC ACID, .BETA.-(BENZOYLAMINO)-.ALPHA.-HYDROXY-, (.ALPHA.R,.BETA.S)-

Preferred Name

English

(2R,3S)-N-BENZOYL-3-PHENYLISOSERINE

Systematic Name

English

Showing 1 to 3 of 3 entries

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Code System

Code

Type

Description

CAS

132201-33-3

PRIMARY

PUBCHEM

2762289

PRIMARY

FDA UNII

D998Q2WJCM

PRIMARY

EPA CompTox

DTXSID10157433

PRIMARY

Showing 1 to 4 of 4 entries

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.ncbi.nlm.nih.gov/pubmed/24900723">https://www.ncbi.nlm.nih.gov/pubmed/24900723</a></span></span></div></div>

Approval Year

Conditions

PubMed

Patents

Sample Use Guides

Description