p-benzoyl-L-phenylalanine

HCID 7020128

Substructure search Find similar structures

Basic information

CAS: 104504-45-2
Standard SMILES: N[C@@H](Cc1ccc(C(=O)c2ccccc2)cc1)C(=O)O
InChIKey: TVIDEEHSOPHZBR-AWEZNQCLSA-N
Molecular formula: C16H15NO3
Average molar mass: 269.29 g/mol
Monoisotopic mass: 269.10519334

Overview

4-benzoyl-L-phenylalanine is a L-phenylalanine derivative that is L-phenylalanine substituted by a benzoyl group at position 4 of the phenyl ring. It is a photoreactive unnatural amino acid that acts as a photo cross-linking probe when incorporated into proteins. It is a member of benzenes, an aromatic ketone and a L-phenylalanine derivative.

Names & identifiers

Preferred name: p-benzoyl-L-phenylalanine
IUPAC: (2S)-2-amino-3-(4-benzoylphenyl)propanoic acid
English name: L-4-Benzoylphenylalanine
Molecular formula: C16H15NO3
Molecular weight: 269.3

Names & synonyms

104504-45-24-benzoyl-l-phenylalaninePara-(Benzoyl)-Phenylalaninep-benzoyl-l-phenylalanineL-Phenylalanine, 4-benzoyl-(2S)-2-amino-3-(4-benzoylphenyl)propanoic acid9RU6KQ9WYDRefChem:169287L-4-Benzoylphenylalanine(S)-2-Amino-3-(4-benzoylphenyl)propanoic acid4-benzoylphenylalanineH-Bpa-OH

Show more names

H-PHE(4-BZ)-OHAl660-1H-4-Bz-Phe-Oh

H-p-Bz-Phe-OHMFCD00238102H-Bpa-OH H-Phe(4-Bz)-OHL-p-Benzoylphenylalanine4-(phenylcarbonyl)-L-phenylalanineH-L-Bpa-OH(2S)-2-Azaniumyl-3-(4-benzoylphenyl)propanoateL-Bpa-OH

Database identifiers

CAS: 104504-45-2
PubChem CID: 7020128
DTXSID: DTXSID20909021
ChEBI: CHEBI:44718
UNII: 9RU6KQ9WYD
EC Number: 811-535-1
Nikkaji: J632.372C

Properties

Computed structural properties

XLogP: 0.2
Topological polar surface area: 80.4 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 5
Heavy atoms: 20
Formal charge: 0
Complexity: 342

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Boiling point: 467.6 · 467.6±40.0 °C(Predicted)
Density: 1.249 · 1.249±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: DMF: insol; DMSO: insol; Ethanol: insol; PBS (pH 7.2): insol
form: A solid
pka: 2.16 · 2.16±0.10(Predicted)
color: White to light yellow
InChI: InChI=1S/C16H15NO3/c17-14(16(19)20)10-11-6-8-13(9-7-11)15(18)12-4-2-1-3-5-12/h1-9,14H,10,17H2,(H,19,20)/t14-/m0/s1
InChIKey: TVIDEEHSOPHZBR-AWEZNQCLSA-N
SMILES: C(O)(=O)[C@H](CC1=CC=C(C(=O)C2=CC=CC=C2)C=C1)N
FDA UNII: 9 RU6KQ9WYD · 9RU6KQ9WYD
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H227
Precautionary statements: 501 · P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235
Safety Statements: 24 · 24/25
HS Code: 29225090 · 29225090

Safety & regulation

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Safety data

hs_code: 29225090
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Hazard statements: H315-H319-H227
Precautionary statements: P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235

Chemistry & industry

Applications · 1 item

Uses4-Benzoyl-L-phenylalanine is a photoreactive amino acid which can easily be incorporated into a peptide by solid-phase synthesis and finds application as phtolabel. It is an important raw material as well as an intermediate in organic synthesis.