N-Benzoyl-(2R,3S)-3-phenylisoserine - ≥98% , CAS No.132201-33-3

CAS: 132201-33-3 Cat. No.: I166958 Molecular Weight: 285.29 EC Number: 631-348-7

GRADE & PURITY ≥98%

Synonyms

Q27276267 | s9395 | SCHEMBL6277 | (2R,3S)-3-BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONIC ACID | (2R,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid | HYJVYOWKYPNSTK-UONOGXRCSA-N | BP-22968 | D998Q2WJCM | F14253 | AC-9033 | BENZENEPROPANOIC ACID, .BETA.-(

Storage

Room temperature

Shipped In

Normal

Overview

It has been proven that the presence of this chiral side chain is essential for the biological activity of paclitaxel. The complex synthesis process of paclitaxel has attracted attention to attaching C-13 side chains to naturally derived taxanes (for example, baccatin III).

Specifications

Synonyms

Q27276267 | s9395 | SCHEMBL6277 | (2R, 3S)-3-BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONIC ACID | (2R, 3S)-3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid | HYJVYOWKYPNSTK-UONOGXRCSA-N | BP-22968 | D998Q2WJCM | F14253 | AC-9033 | BENZENEPROPANOIC ACID, .BETA.-(

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488193280
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488193280
• Canonical Smiles: C1=CC=C(C=C1)C(C(C(=O)O)O)NC(=O)C2=CC=CC=C2
• IUPAC Name: (2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoic acid
• 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
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@H](C(=O)O)O)NC(=O)C2=CC=CC=C2
• WGK Germany: 3
• Molecular Weight: 285.29
• Reaxy-Rn: 3383978
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3383978&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Benzamides
          • Level6 N-benzylbenzamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Benzamides
• Direct Parent: N-benzylbenzamides
• Alternative Parents: Phenylpropanoic acids Beta amino acids and derivatives Benzoyl derivatives Monosaccharides Alpha hydroxy acids and derivatives Secondary carboxylic acid amides Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: N-benzylbenzamide - Beta amino acid or derivatives - 3-phenylpropanoic-acid - Benzoyl - Alpha-hydroxy acid - Hydroxy acid - Monosaccharide - Carboxamide group - Secondary carboxylic acid amide - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-benzylbenzamides. These are compounds containing a benzamide moiety that is N-linked to a benzyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

B16 (5829 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

L6 (7924 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: -40°, c = 1.0 in ethanol
• Melt Point(°C): 169-172°C
• Molecular Weight: 285.290 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 285.1 Da
• Monoisotopic Mass: 285.1 Da
• Topological Polar Surface Area: 86.600 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 359.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Kui Zhang, Liangqin Zhou, Fan Chen, Yuanwei Chen, Xianglin Luo.  (2019)  Injectable gel self-assembled by paclitaxel itself for in situ inhibition of tumor growth.  JOURNAL OF CONTROLLED RELEASE,      [PMID:31669210] [10.1016/j.jconrel.2019.10.002]