2-{2-[(2S)-2-[(2E)-3-(furan-2-yl)prop-2-enamido]-3-phenylpropanamido]acetamido}acetic acid

• ChemBase ID: 133376
• Molecular Formular: C20H21N3O6
• Molecular Mass: 399.39724
• Monoisotopic Mass: 399.14303541
• SMILES: c1ccc(cc1)C[C@@H](C(=O)NCC(=O)NCC(=O)O)NC(=O)/C=C/c1ccco1
• Canonical SMILES: O=C(NCC(=O)O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)/C=C/c1ccco1
• InChI: InChI=1S/C20H21N3O6/c24-17(9-8-15-7-4-10-29-15)23-16(11-14-5-2-1-3-6-14)20(28)22-12-18(25)21-13-19(26)27/h1-10,16H,11-13H2,(H,21,25)(H,22,28)(H,23,24)(H,26,27)/b9-8+/t16-/m0/s1
• InChIKey: ZDLZKMDMBBMJLI-FDMDGMSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(2S)-2-[(2E)-3-(furan-2-yl)prop-2-enamido]-3-phenylpropanamido]acetamido}acetic acid; 2-{2-[(2S)-2-[3-(furan-2-yl)prop-2-enamido]-3-phenylpropanamido]acetamido}acetic acid
• IUPAC Traditional name: {2-[(2S)-2-[(2E)-3-(furan-2-yl)prop-2-enamido]-3-phenylpropanamido]acetamido}acetic acid; {2-[(2S)-2-[3-(furan-2-yl)prop-2-enamido]-3-phenylpropanamido]acetamido}acetic acid
• Synonyms: FAPGG; N-[3-(2-Furyl)acryloyl]-L-phenylalanyl-glycyl-glycine; N-[3-(2-Furyl)acryloyl]-Phe-Gly-Gly

Database IDs

• CAS Number: 64967-39-1
• MDL Number: MFCD00036816
• PubChem SID: 162227653; 24894929
• PubChem CID: 6438387

CALCULATED PROPERTIES

• Acid pKa: 3.6463664
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.7454594
• LogD (pH = 7.4): -3.2208865
• Log P: 0.105573796
• Molar Refractivity: 102.9742 cm^3
• Polarizability: 39.274113 Å^3
• Polar Surface Area: 137.74 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M NH4OH: soluble50 mg/mL, clear to slightly turbid, yellow

Safety Information

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

Pharmacology Properties

• Gene Information: human ... ACE(1636), ACE2(59272)mouse ... ACE3(217246)rat ... ACE(11421), ACE2(70008), ACE3(498012)

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C20H21N3O6

DETAILS

Sigma Aldrich - F7131

Amino Acid Sequence
FA-Phe-Gly-Gly
Substrates
A substrate for continuous spectrophotometric assay of angiotensin converting enzyme (ACE).

Sigma Aldrich - 48176

Amino Acid Sequence
FA-Phe-Gly-Gly
Other Notes
Substrate for the continuous spectrophotometric assay of angiotensin converting enzyme1