L-Aspartyl-L-phenylalanine

HCID 93078

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Basic information

CAS: 13433-09-5
Standard SMILES: N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O
InChIKey: YZQCXOFQZKCETR-UWVGGRQHSA-N
Molecular formula: C13H16N2O5
Average molar mass: 280.28 g/mol
Monoisotopic mass: 280.10592161

Overview

Asp-Phe is a dipeptide formed from L-alpha-aspartyl and L-phenylalanine residues. It is obtained after the hydrolysis of aspartame in intestinal lumen. It has a role as a human xenobiotic metabolite and a human blood serum metabolite.

Names & identifiers

Preferred name: L-Aspartyl-L-phenylalanine
IUPAC: (3S)-3-amino-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobutanoic acid
English name: H-Asp-Phe-OH
Molecular formula: C13H16N2O5
Molecular weight: 280.28

Names & synonyms

13433-09-5L-Aspartyl-L-phenylalanineAspartyl-phenylalanineAspartylphenylalanineN-L-alpha-aspartyl-L-PhenylAlanineDTXSID20928570(3S)-3-amino-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobutanoic acid(3S)-3-amino-4-(((1S)-1-carboxy-2-phenylethyl)amino)-4-oxobutanoic acidRefChem:114637DTXCID801357335236-557-3H-ASP-PHE-OH

Show more names

AI311009AI3 11009AI3-11009Asp-Phe-OHL-Asp-L-PheAsp-Phe 96%ASPARTAME ACID

ASP-PHE(S)-3-Amino-4-(((S)-1-carboxy-2-phenylethyl)amino)-4-oxobutanoic acidDemethylaspartameAspartame EP Impurity BL-alpha-Aspartyl-L-phenylalanineMFCD00063155CHEMBL170376alpha-L-Aspartyl-L-phenylalanine

Database identifiers

CAS: 13433-09-5
PubChem CID: 93078
DTXSID: DTXSID20928570
ChEMBL: CHEMBL170376
ChEBI: CHEBI:73830
EC Number: 236-557-3
Nikkaji: J27.535B

Properties

Computed structural properties

XLogP: -3.3
Topological polar surface area: 130 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 6
Rotatable bonds: 7
Heavy atoms: 20
Formal charge: 0
Complexity: 366

Experimental & physicochemical properties

Melting Point236 - 239 °C

Physical DescriptionSolid

Collision Cross Section164.9 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Melting point: 236 · 236-239 °C(lit.)
Boiling point: 423 °C · 423°C (rough estimate)
Density: 1.2419 · 1.2419 (rough estimate)
refractive index: 1.645 · 1.6450 (estimate)
storage temp.: 2 · Keep in dark place,Sealed in dry,2-8°C
solubility: 5 · DMSO:5.0(Max Conc. mg/mL);17.84(Max Conc. mM)DMSO:PBS (pH 7.2) (1:2):0.3(Max Conc. mg/mL);1.07(Max Conc. mM)
form: Powder
pka: 3.35 · 3.35±0.10(Predicted)
color: Off-white to yellow to beige to orange to tan
optical activity: 20 · [α]20/D +12.5°, c = 1 in 0.5 M HCl
BRN: 2817528 · 2817528
Major Application: peptide synthesis
InChI: InChI=1/C13H16N2O5/c14-9(7-11(16)17)12(18)15-10(13(19)20)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,14H2,(H,15,18)(H,16,17)(H,19,20)/t9-,10-/s3
InChIKey: YZQCXOFQZKCETR-DPIMBTEZNA-N
SMILES: C1(=CC=CC=C1)C[C@@H](C(=O)O)NC(=O)[C@@H](N)CC(=O)O |&1:7,14,r|
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P271-P280
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
HS Code: 29242990 · 29242990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29242990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P271-P280

Chemistry & industry

Applications

UsesL-Aspartyl-L-phenylalanine is an impurity of Thiamine (T344185). Thiamine Impurity B.

Suppliers100 total

郑州阿尔法化工有限公司+86-18530059196 · [email protected]

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

济南百隆化学有限公司[email protected] · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

Additional notes

DefinitionChEBI: A dipeptide formed from L-alpha-aspartyl and L-phenylalanine residues. It is obtained after the hydrolysis of aspartame in intestinal lumen.