(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-3-carboxy-2-[(2S)-2-[(2S)-4-carboxy-2-[(2S)-3-carboxy-2-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamido]propanamido]butanamido]-3-methylbutanamido]propanamido]propanoyl]pyrrolidin-2-yl]formamido}-6-[(2,4-dinitrophenyl)amino]hexanoic acid

• ChemBase ID: 132289
• Molecular Formular: C50H62N10O22
• Molecular Mass: 1155.08108
• Monoisotopic Mass: 1154.40401367
• SMILES: C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)Cc1cc(=O)oc2c1ccc(c2)OC
• Canonical SMILES: COc1ccc2c(c1)oc(=O)cc2CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)O)CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C)CC(=O)O)C(C)C)CCC(=O)O)CC(=O)O
• InChI: InChI=1S/C50H62N10O22/c1-24(2)43(57-44(69)31(14-15-39(62)63)54-46(71)33(22-40(64)65)53-38(61)18-26-19-42(68)82-37-21-28(81-4)11-12-29(26)37)48(73)56-34(23-41(66)67)45(70)52-25(3)49(74)58-17-7-9-35(58)47(72)55-32(50(75)76)8-5-6-16-51-30-13-10-27(59(77)78)20-36(30)60(79)80/h10-13,19-21,24-25,31-35,43,51H,5-9,14-18,22-23H2,1-4H3,(H,52,70)(H,53,61)(H,54,71)(H,55,72)(H,56,73)(H,57,69)(H,62,63)(H,64,65)(H,66,67)(H,75,76)/t25-,31-,32-,33-,34-,35-,43-/m0/s1
• InChIKey: YOUVSUDOGAVRQX-AEAFXXELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S)-3-carboxy-2-[(2S)-2-[(2S)-4-carboxy-2-[(2S)-3-carboxy-2-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamido]propanamido]butanamido]-3-methylbutanamido]propanamido]propanoyl]pyrrolidin-2-yl]formamido}-6-[(2,4-dinitrophenyl)amino]hexanoic acid
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S)-3-carboxy-2-[(2S)-2-[(2S)-4-carboxy-2-[(2S)-3-carboxy-2-[2-(7-methoxy-2-oxochromen-4-yl)acetamido]propanamido]butanamido]-3-methylbutanamido]propanamido]propanoyl]pyrrolidin-2-yl]formamido}-6-[(2,4-dinitrophenyl)amino]hexanoic acid
• Synonyms: 7-Methoxycoumarin-4-acetyl-Asp-Glu-Val-Asp-Ala-Pro-(2,4-dinitrophenyl)Lys

Database IDs

• CAS Number: 189696-20-6
• MDL Number: MFCD00798785
• PubChem SID: 162226566
• PubChem CID: 71308540

CALCULATED PROPERTIES

• Acid pKa: 3.062973
• H Acceptors: 22
• H Donor: 11
• LogD (pH = 5.5): -7.635818
• LogD (pH = 7.4): -13.710357
• Log P: -0.71328634
• Molar Refractivity: 277.4825 cm^3
• Polarizability: 105.89873 Å^3
• Polar Surface Area: 483.31 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

DETAILS

Sigma Aldrich - M1169

Amino Acid Sequence
MCA-Asp-Glu-Val-Asp-Ala-Pro-Lys-DNP
Biochem/physiol Actions
Fluorogenic substrate for caspase 3 and caspase 3-like enzymes. Cleavage at the P1 Asp residue results in continuous fluorescence at 392 nm.