19-[2-amino-3-(2H5)phenyl(2H3)propanamido]-10-(4-aminobutyl)-16-benzyl-N-(1,3-dihydroxybutan-2-yl)-7-(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide

• ChemBase ID: 175803
• Molecular Formular: C49H66N10O10S2
• Molecular Mass: 1019.23934
• Monoisotopic Mass: 1018.44048036
• SMILES: C1(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC1C(O)C)CCCCN)Cc1c2c([nH]c1)cccc2)Cc1ccccc1)NC(=O)C(Cc1ccccc1)N)C(=O)NC(C(O)C)CO
• Canonical SMILES: NCCCCC1NC(=O)C(NC(=O)C(Cc2ccccc2)NC(=O)C(CSSCC(NC(=O)C(NC1=O)C(O)C)C(=O)NC(C(O)C)CO)NC(=O)C(Cc1ccccc1)N)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)
• InChIKey: DEQANNDTNATYII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 19-[2-amino-3-(^2H₅)phenyl(^2H₃)propanamido]-10-(4-aminobutyl)-16-benzyl-N-(1,3-dihydroxybutan-2-yl)-7-(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
• IUPAC Traditional name: 19-[2-amino-3-(^2H₅)phenyl(^2H₃)propanamido]-10-(4-aminobutyl)-16-benzyl-N-(1,3-dihydroxybutan-2-yl)-7-(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
• Synonyms: D-(Phenylalanyl-d8)-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-L-cysteinamide Cyclic (2-7)-Disulfide di-Trifluoroacetic Acid Salt; SMS 201-995-d8 di-Trifluoroacetic Acid Salt; Sandostatin-d8 di-Trifluoroacetic Acid Salt; Sandostatin LAR-d8 di-Trifluoroacetic Acid Salt; Octreotide-phenylalanine-d8 di-Trifluoroacetic Acid Salt

Database IDs

• PubChem SID: 164231713
• PubChem CID: 46782611

CALCULATED PROPERTIES

• Acid pKa: 11.401009
• H Acceptors: 12
• H Donor: 13
• LogD (pH = 5.5): -6.369599
• LogD (pH = 7.4): -4.2777534
• Log P: -1.4112649
• Molar Refractivity: 269.7696 cm^3
• Polarizability: 107.01645 Å^3
• Polar Surface Area: 332.22 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O239952

Labelled octapeptide analog of Somatostatin. A gastric antisecretory agent. Used in treatment of acromegaly.

REFERENCES

• Bauer, W., et al.: Life Sci., 31, 1133 (1982)
• Plewe, G., et al.: Lancet, 2, 782 (1982)
• Kraenzlin, M.E., et al.: Experientia, 41, 738 (1982)
• del Pozo, E., et al.: Acta Endocrinol., 111, 433 (1982)