(4S,7R,10R,13S,16R,19S,22S,25S,28R,31R,34R,37R)-19,34-bis(4-aminobutyl)-37-{2-[(2R)-2-aminopropanamido]acetamido}-13,25,28-tribenzyl-31-(carbamoylmethyl)-10,16-bis[(1R)-1-hydroxyethyl]-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontane-4-carboxylic acid

• ChemBase ID: 103827
• Molecular Formular: C76H104N18O19S2
• Molecular Mass: 1637.87816
• Monoisotopic Mass: 1636.7166552
• SMILES: C[C@@H](N)C(=O)NCC(=O)N[C@@H]1CSSC[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3c2cccc3)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](CC(=O)N)NC(=O)[C@H](CCCCN)NC1=O)[C@@H](C)O)[C@@H](C)O)C(=O)O
• Canonical SMILES: NCCCC[C@@H]1NC(=O)[C@@H](CSSC[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CC(=O)N)Cc1ccccc1)Cc1ccccc1)Cc1c[nH]c2c1cccc2)CCCCN)[C@H](O)C)[C@H](O)C)C(=O)O)NC(=O)CNC(=O)[C@H](N)C
• InChI: InChI=1S/C76H104N18O19S2/c1-41(79)64(100)82-37-61(99)83-58-39-114-115-40-59(76(112)113)92-72(108)57(38-95)91-75(111)63(43(3)97)94-71(107)54(33-46-23-11-6-12-24-46)90-74(110)62(42(2)96)93-66(102)51(28-16-18-30-78)84-69(105)55(34-47-36-81-49-26-14-13-25-48(47)49)88-68(104)53(32-45-21-9-5-10-22-45)86-67(103)52(31-44-19-7-4-8-20-44)87-70(106)56(35-60(80)98)89-65(101)50(85-73(58)109)27-15-17-29-77/h4-14,19-26,36,41-43,50-59,62-63,81,95-97H,15-18,27-35,37-40,77-79H2,1-3H3,(H2,80,98)(H,82,100)(H,83,99)(H,84,105)(H,85,109)(H,86,103)(H,87,106)(H,88,104)(H,89,101)(H,90,110)(H,91,111)(H,92,108)(H,93,102)(H,94,107)(H,112,113)/t41-,42-,43-,50-,51+,52-,53+,54+,55+,56-,57-,58+,59-,62-,63-/m1/s1
• InChIKey: NHXLMOGPVYXJNR-NZDSOPRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,7R,10R,13S,16R,19S,22S,25S,28R,31R,34R,37R)-19,34-bis(4-aminobutyl)-37-{2-[(2R)-2-aminopropanamido]acetamido}-13,25,28-tribenzyl-31-(carbamoylmethyl)-10,16-bis[(1R)-1-hydroxyethyl]-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontane-4-carboxylic acid
• IUPAC Traditional name: (4S,7R,10R,13S,16R,19S,22S,25S,28R,31R,34R,37R)-19,34-bis(4-aminobutyl)-37-{2-[(2R)-2-aminopropanamido]acetamido}-13,25,28-tribenzyl-31-(carbamoylmethyl)-10,16-bis[(1R)-1-hydroxyethyl]-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontane-4-carboxylic acid
• Synonyms: Ala-Gly-Cys-Lys-Asn-Phe-Phe-D-Trp-Lys-Thr-Phe-Thr-Ser-Cys; [D-Trp^8]-SOMATOSTATIN

Database IDs

• CAS Number: 58976-46-8
• PubChem SID: 162091353
• PubChem CID: 71299696

CALCULATED PROPERTIES

• Acid pKa: 2.8840423
• H Acceptors: 22
• H Donor: 22
• LogD (pH = 5.5): -13.368184
• LogD (pH = 7.4): -11.055386
• Log P: -8.234492
• Molar Refractivity: 420.26 cm^3
• Polarizability: 165.9829 Å^3
• Polar Surface Area: 613.23 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02152994

Contains a disulfide bond between Cys3 and Cys14. A potent somatostatin analog.

REFERENCES

• Rivier, J., et al., Biochem. Biophys. Res. Commun., 65: 746, (1975).
• Brown, M., et al., Science, 196: 1467, (1977).
• Reubl, J.C., et al., Endocrinology, 110: 1049, (1982).