(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-(2-{[(2S)-1-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-5-yl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-4-methylpentanamido]hexanoyl]pyrrolidin-2-yl]formamido}acetamido)-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanamido]-3-(4-hydroxyphenyl)propanoic acid

• ChemBase ID: 103386
• Molecular Formular: C82H114N20O17S
• Molecular Mass: 1683.97136
• Monoisotopic Mass: 1682.83915329
• SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccc(O)cc1)CCSC)[C@H]1N(C(=O)[C@@H](NC(=O)CNC(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)Cc3c4ccccc4[nH]c3)Cc3[nH]cnc3)Cc3c4ccccc4[nH]c3)CC(C)C)CCC(=O)N)CC(C)C)CCCCN)CCC2)CCC(=O)N)CCC1
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)O)CCSC)CCC(=O)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)N)Cc1[nH]cnc1)CC(C)C)CCC(=O)N)CC(C)C
• InChI: InChI=1S/C82H114N20O17S/c1-45(2)34-61(98-76(112)63(38-49-41-89-56-17-9-7-15-53(49)56)99-77(113)64(39-50-42-87-44-91-50)96-71(107)54(84)37-48-40-88-55-16-8-6-14-52(48)55)74(110)93-57(25-27-68(85)104)72(108)97-62(35-46(3)4)75(111)95-59(18-10-11-30-83)80(116)101-31-12-19-66(101)78(114)90-43-70(106)92-60(26-28-69(86)105)81(117)102-32-13-20-67(102)79(115)94-58(29-33-120-5)73(109)100-65(82(118)119)36-47-21-23-51(103)24-22-47/h6-9,14-17,21-24,40-42,44-46,54,57-67,88-89,103H,10-13,18-20,25-39,43,83-84H2,1-5H3,(H2,85,104)(H2,86,105)(H,87,91)(H,90,114)(H,92,106)(H,93,110)(H,94,115)(H,95,111)(H,96,107)(H,97,108)(H,98,112)(H,99,113)(H,100,109)(H,118,119)/t54-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-/m0/s1
• InChIKey: SBKVPJHMSUXZTA-MEJXFZFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-(2-{[(2S)-1-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-5-yl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-4-methylpentanamido]hexanoyl]pyrrolidin-2-yl]formamido}acetamido)-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanamido]-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-(2-{[(2S)-1-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(3H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]-4-carbamoylbutanamido]-4-methylpentanamido]hexanoyl]pyrrolidin-2-yl]formamido}acetamido)-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanamido]-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: Trp-His-Trp-Leu-Gln-Leu-Lys-Pro-Gly-Gln-Pro-Met-Tyr; α₁-MATING FACTOR

Database IDs

• CAS Number: 59401-28-4
• PubChem SID: 162103295
• PubChem CID: 71299812

CALCULATED PROPERTIES

• Acid pKa: 3.2628043
• H Acceptors: 20
• H Donor: 19
• LogD (pH = 5.5): -7.137754
• LogD (pH = 7.4): -5.013163
• Log P: -4.6617117
• Molar Refractivity: 441.4963 cm^3
• Polarizability: 174.17435 Å^3
• Polar Surface Area: 587.63 Å^2
• Rotatable Bonds: 48
• Lipinski's Rule of Five: false

REFERENCES

• Matsui, Y., et al., Biochem. Biophys. Res. Commun., 78: 534, (1977).