(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-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: 130475
• Molecular Formular: C49H66N10O10S2
• Molecular Mass: 1019.23934
• Monoisotopic Mass: 1018.44048036
• SMILES: C[C@@H](O)[C@@H](CO)NC(=O)[C@H]1CSSC[C@H](NC(=O)[C@H](N)Cc2ccccc2)C(=O)N[C@H](Cc2ccccc2)C(=O)N[C@H](Cc2c[nH]c3ccccc23)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(C)O)C(=O)N1
• Canonical SMILES: NCCCC[C@@H]1NC(=O)[C@H](NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CSSC[C@@H](NC(=O)[C@H](NC1=O)C(O)C)C(=O)N[C@@H]([C@H](O)C)CO)NC(=O)[C@@H](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)/t28-,29?,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1
• InChIKey: DEQANNDTNATYII-RRCPSWKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-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: (4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-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
• Brand Name: Sandostatin
• Synonyms: Octreotide

Database IDs

• CAS Number: 83150-76-9
• PubChem SID: 162224754
• PubChem CID: 6400441; 54373
• ATC CODE: H01CB02
• CHEMBL: 1680
• Chemspider ID: 10482007
• DrugBank ID: DB00104
• KEGG ID: D00442
• Unique Ingredient Identifier: RWM8CCW8GP
• Wikipedia Title: Octreotide

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: 106.99345 Å^3
• Polar Surface Area: 332.22 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Subcutaneous, intramuscular, intravenous
• Bioavailability: 100%; I.M.: 60% to 63% of subcutaneous dose
• Half Life: 1.7–1.9 hours
• Metabolism: Hepatic
• Protein Bound: 65%
• Legal Status: Rx
• Pregnancy Category: B (US)