(4S)-4-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{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]-3-hydroxypropanamido}-3-phenylpropanamido]-3-hydroxypropanamido]hexanamido]acetamido}-5-[(2S)-2-{[(1S)-1-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}pyrrolidin-1-yl]-5-oxopentanoic acid

• ChemBase ID: 103885
• Molecular Formular: C81H106N18O19S
• Molecular Mass: 1667.88254
• Monoisotopic Mass: 1666.76023426
• SMILES: CSCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)C(CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H](N)Cc1c[nH]c2ccccc12)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O
• Canonical SMILES: NCCCC[C@@H](C(=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)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(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)CO)Cc1ccccc1)CO
• InChI: InChI=1S/C81H106N18O19S/c1-45(2)32-60(93-75(111)62(36-49-39-86-56-19-10-8-17-53(49)56)95-76(112)63(37-50-40-84-44-88-50)92-70(106)54(83)35-48-38-85-55-18-9-7-16-52(48)55)73(109)97-66(43-101)78(114)94-61(33-46-14-5-4-6-15-46)74(110)98-65(42-100)77(113)90-57(20-11-12-29-82)71(107)87-41-68(103)89-59(26-27-69(104)105)80(116)99-30-13-21-67(99)79(115)91-58(28-31-119-3)72(108)96-64(81(117)118)34-47-22-24-51(102)25-23-47/h4-10,14-19,22-25,38-40,44-45,54,57-67,85-86,100-102H,11-13,20-21,26-37,41-43,82-83H2,1-3H3,(H,84,88)(H,87,107)(H,89,103)(H,90,113)(H,91,115)(H,92,106)(H,93,111)(H,94,114)(H,95,112)(H,96,108)(H,97,109)(H,98,110)(H,104,105)(H,117,118)/t54-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66?,67-/m0/s1
• InChIKey: UHCQKQGHSBZHIZ-SJIJVUAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{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]-3-hydroxypropanamido}-3-phenylpropanamido]-3-hydroxypropanamido]hexanamido]acetamido}-5-[(2S)-2-{[(1S)-1-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}pyrrolidin-1-yl]-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-4-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{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]-3-hydroxypropanamido}-3-phenylpropanamido]-3-hydroxypropanamido]hexanamido]acetamido}-5-[(2S)-2-{[(1S)-1-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}pyrrolidin-1-yl]-5-oxopentanoic acid
• Synonyms: α-SK2-Mating Factor; TRP-HIS-TRP-LEU-SER-PHE-SER-LYS-GLY-GLU-PRO-MET-TYR

Database IDs

• CAS Number: 89718-47-8
• PubChem SID: 162091400
• PubChem CID: 71299699

CALCULATED PROPERTIES

• Acid pKa: 3.0996273
• H Acceptors: 22
• H Donor: 21
• LogD (pH = 5.5): -7.2896976
• LogD (pH = 7.4): -6.997807
• Log P: -6.9694667
• Molar Refractivity: 433.4052 cm^3
• Polarizability: 170.96501 Å^3
• Polar Surface Area: 588.0 Å^2
• Rotatable Bonds: 48
• Lipinski's Rule of Five: false

REFERENCES

• Sakurai, A., et al., FEBS Lett., 166: 339, (1984).