(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-hydroxypropanamido]-3-methylbutanamido]-3-carbamoylpropanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-3-hydroxypropanamido]acetamido}-4-methylpentanamido]-5-carbamimidamidopentanamido]hexanamido]-4-(methylsulfanyl)butanamido]propanoic acid

• ChemBase ID: 154124
• Molecular Formular: C66H119N21O22S
• Molecular Mass: 1590.84356
• Monoisotopic Mass: 1589.85592555
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)N)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)C)CCSC)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)N)CO)CC(=O)N)CO)CC(C)C)CCC(=O)N)CO)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C66H119N21O22S/c1-30(2)23-40(57(100)78-37(16-14-21-73-66(71)72)55(98)77-36(15-12-13-20-67)54(97)80-39(19-22-110-11)53(96)75-34(9)65(108)109)76-48(94)26-74-52(95)43(27-88)83-56(99)38(17-18-46(68)92)79-58(101)41(24-31(3)4)81-64(107)51(35(10)91)87-61(104)44(28-89)84-59(102)42(25-47(69)93)82-63(106)50(33(7)8)86-60(103)45(29-90)85-62(105)49(70)32(5)6/h30-45,49-51,88-91H,12-29,67,70H2,1-11H3,(H2,68,92)(H2,69,93)(H,74,95)(H,75,96)(H,76,94)(H,77,98)(H,78,100)(H,79,101)(H,80,97)(H,81,107)(H,82,106)(H,83,99)(H,84,102)(H,85,105)(H,86,103)(H,87,104)(H,108,109)(H4,71,72,73)/t34-,35+,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,49-,50-,51-/m0/s1
• InChIKey: KPAXWJVUQQAPFD-KZVXTNNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-hydroxypropanamido]-3-methylbutanamido]-3-carbamoylpropanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-3-hydroxypropanamido]acetamido}-4-methylpentanamido]-5-carbamimidamidopentanamido]hexanamido]-4-(methylsulfanyl)butanamido]propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-hydroxypropanamido]-3-methylbutanamido]-3-carbamoylpropanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-3-hydroxypropanamido]acetamido}-4-methylpentanamido]-5-carbamimidamidopentanamido]hexanamido]-4-(methylsulfanyl)butanamido]propanoic acid
• Synonyms: L-Valyl-L-seryl-L-valyl-L-asparaginyl-L-seryl-L-threonyl-L-leucyl-L-glutaminyl-L-serylglycyl-L-leucyl-L-arginyl-L-lysyl-L-methionyl-L-alanine; Val-Ser-Val-Asn- Ser-Thr-Leu-Gln-Ser-Gly-Leu-Arg-Lys-Met-Ala; SARS Protease Substrate

Database IDs

• CAS Number: 587886-51-9
• MDL Number: MFCD08274404
• PubChem SID: 162248263
• PubChem CID: 71311797

CALCULATED PROPERTIES

• Acid pKa: -1.0091264
• H Acceptors: 27
• H Donor: 26
• LogD (pH = 5.5): -18.362513
• LogD (pH = 7.4): -16.267036
• Log P: -13.064628
• Molar Refractivity: 402.3959 cm^3
• Polarizability: 154.46211 Å^3
• Polar Surface Area: 725.74 Å^2
• Rotatable Bonds: 55
• 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

Product Information

• Purity: ≥85% (HPLC)
• Empirical Formula (Hill Notation): C66H119N21O22S

DETAILS

Sigma Aldrich - 07859

Application
Enzyme substrate for the assays of the SARS coronavirus main protease2
Biochem/physiol Actions
A study for determining substrate specificity for the SARS main protease indicated that the best substrates contained residues with high β-sheet propensity at positions P5 and P3., small hydrophobic residues at P4, hydrophobic residues without β-branching at residue P2 and a GLN for residue P1. 1