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132201-33-3 molecular structure
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(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoic acid

ChemBase ID: 146887
Molecular Formular: C16H15NO4
Molecular Mass: 285.2946
Monoisotopic Mass: 285.10010797
SMILES and InChIs

SMILES:
c1ccc(cc1)[C@@H]([C@H](C(=O)O)O)NC(=O)c1ccccc1
Canonical SMILES:
O=C(c1ccccc1)N[C@H]([C@H](C(=O)O)O)c1ccccc1
InChI:
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
InChIKey:
HYJVYOWKYPNSTK-UONOGXRCSA-N

Cite this record

CBID:146887 http://www.chembase.cn/molecule-146887.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoic acid
IUPAC Traditional name
(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoic acid
Synonyms
N-Benzoyl-(2R,3S)-3-phenylisoserine
(αR,βS)-β-(Benzoylamino)-α-hydroxybenzenepropanoic Acid
[R-(R*,S*)]-β-(benzoylamino)-α-hydroxybenzenepropanoic Acid
(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropionic Acid
(2R,3S)-N-Benzoyl-3-phenylisoserine
(2R,3S)-N-Benzoyl-3-phenyl Isoserine
(2R,3S)-3-Benzamido-2-hydroxy-3-phenylpropanoic acid
N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸
CAS Number
132201-33-3
MDL Number
MFCD00274633
PubChem SID
162241079
24868119
PubChem CID
2762289

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 2762289 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.6921208  H Acceptors
H Donor LogD (pH = 5.5) 0.025214426 
LogD (pH = 7.4) -1.4769937  Log P 1.83164 
Molar Refractivity 76.4381 cm3 Polarizability 29.423927 Å3
Polar Surface Area 86.63 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
169-172 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -40°, c = 1.0 in ethanol expand Show data source
Storage Condition
Refrigerator expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
95+% expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
C6H5CONHCH(C6H5)CH(OH)CO2H expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 444375 external link
Packaging
500 mg in glass bottle
Application
The presence of this chiral side chain has proven to be essential for the biological activity of taxol,1,2,3 one of the most promising anticancer agents being investigated.4,5 The challenging synthesis of taxol has stimulated interest in the attachment of the C-13 side chain to naturally derived taxanes like baccatin III.6,7,8
Toronto Research Chemicals - B208550 external link
(2R,3S)-N-Benzoyl-3-phenylisoserine is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-N-Benzoyl-3-phenylisoserine shows cytotoxic, antiviral and immunomodulatory

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Paal, K. et al.: Bioorg. Med. Chem., 15, 1323 (2007)
  • • Krawczyk, E. et al.: J. Pharm. Pharmacol., 57, 791 (2007)
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PATENTS

PATENTS

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INTERNET

INTERNET

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