(3S)-3-[(2S)-2-[(2S)-2-[(2S)-3-carboxy-2-[(2S)-2-acetamido-3-methylbutanamido]propanamido]-3-methylbutanamido]propanamido]-4-oxobutanoic acid

• ChemBase ID: 153615
• Molecular Formular: C23H37N5O10
• Molecular Mass: 543.56738
• Monoisotopic Mass: 543.25404241
• SMILES: C[C@@H](C(=O)N[C@@H](CC(=O)O)C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)C
• Canonical SMILES: O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)C)CC(=O)O)C)CC(=O)O
• InChI: InChI=1S/C23H37N5O10/c1-10(2)18(25-13(6)30)23(38)27-15(8-17(33)34)21(36)28-19(11(3)4)22(37)24-12(5)20(35)26-14(9-29)7-16(31)32/h9-12,14-15,18-19H,7-8H2,1-6H3,(H,24,37)(H,25,30)(H,26,35)(H,27,38)(H,28,36)(H,31,32)(H,33,34)/t12-,14-,15-,18-,19-/m0/s1
• InChIKey: OOGHGBCRVSBUHH-GOYXDOSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-3-carboxy-2-[(2S)-2-acetamido-3-methylbutanamido]propanamido]-3-methylbutanamido]propanamido]-4-oxobutanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-3-carboxy-2-[(2S)-2-acetamido-3-methylbutanamido]propanamido]-3-methylbutanamido]propanamido]-4-oxobutanoic acid
• Synonyms: Ac-VDVAD-CHO; N-Acetyl-Val-Asp-Val-Ala-Asp-CHO

Database IDs

• CAS Number: 194022-51-0
• MDL Number: MFCD01862574
• PubChem SID: 162247754
• PubChem CID: 9850347

CALCULATED PROPERTIES

• Acid pKa: 3.7495322
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -5.418324
• LogD (pH = 7.4): -8.761124
• Log P: -2.5731902
• Molar Refractivity: 128.2673 cm^3
• Polarizability: 50.619812 Å^3
• Polar Surface Area: 237.17 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• 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: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C22H33N5O11

DETAILS

Sigma Aldrich - A2222

Amino Acid Sequence
Ac-Val-Asp-Val-Ala-Asp-CHO
Substrates
Caspase-2 inhibitor. May also show some inhibitory activity against caspase-3.1