benzyl N-{2-[(2S)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]pyrrolidin-1-yl]-2-oxoethyl}carbamate

• ChemBase ID: 103288
• Molecular Formular: C25H25N3O6
• Molecular Mass: 463.4825
• Monoisotopic Mass: 463.17433554
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)OCc1ccccc1)c2
• Canonical SMILES: O=C(OCc1ccccc1)NCC(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• InChI: InChI=1S/C25H25N3O6/c1-16-12-23(30)34-21-13-18(9-10-19(16)21)27-24(31)20-8-5-11-28(20)22(29)14-26-25(32)33-15-17-6-3-2-4-7-17/h2-4,6-7,9-10,12-13,20H,5,8,11,14-15H2,1H3,(H,26,32)(H,27,31)/t20-/m0/s1
• InChIKey: YWOXKKRKNGWXEG-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-{2-[(2S)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]pyrrolidin-1-yl]-2-oxoethyl}carbamate
• IUPAC Traditional name: benzyl N-{2-[(2S)-2-[(4-methyl-2-oxochromen-7-yl)carbamoyl]pyrrolidin-1-yl]-2-oxoethyl}carbamate
• Synonyms: Z-Gly-Pro-4-methyl-7-coumarinylamide; Z-Gly-Pro 7-amido-4-methylcoumarin; GLYCYL-L-PROLINE 4-METHYL-COUMARYL-7-AMIDE; Z-Gly-Pro-AMC; Z-GP-AMC; Z-Gly-Pro-7-Amino-4-Methylcoumarin

Database IDs

• CAS Number: 68542-93-8
• MDL Number: MFCD00038082
• Beilstein Number: 466316
• PubChem SID: 162090448; 24890280
• PubChem CID: 125702

CALCULATED PROPERTIES

• Acid pKa: 12.80138
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.295092
• LogD (pH = 7.4): 2.2950907
• Log P: 2.295092
• Molar Refractivity: 124.7198 cm^3
• Polarizability: 47.328156 Å^3
• Polar Surface Area: 114.04 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 96-102 °C(lit.)
• Optical Rotation: [α]20/D -123±6°, c = 1% in DMF

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Grade: for fluorescence
• Suitability: in accordance for fluorescence
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C25H25N3O6

DETAILS

MP Biomedicals - 02151203

Substrate for X-prolyl dipeptidyl-aminopeptidase

Sigma Aldrich - 96280

Other Notes
Fluorogenic substrate for post-proline cleaving enzyme (prolyl endopeptidase1

REFERENCES

• Imai, K., et al., J. Biochem. (Tokyo), 93: 431, (1983).