(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-[(1R)-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: 153754
• Molecular Formular: C49H66N10O10S2
• Molecular Mass: 1019.23934
• Monoisotopic Mass: 1018.44048036
• SMILES: C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N1)CCCCN)Cc1c[nH]c2c1cccc2)Cc1ccccc1)NC(=O)[C@@H](Cc1ccccc1)N)C(=O)N[C@H](CO)[C@@H](C)O)O
• 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@H](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-OULOTJBUSA-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-[(1R)-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-[(1R)-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: SMS 201-995; Octreotide

Database IDs

• CAS Number: 83150-76-9
• MDL Number: MFCD00871400
• PubChem SID: 162247893
• PubChem CID: 448601

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

Physical Property

• Solubility: H2O: soluble

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C49H66N10O10S2

DETAILS

Sigma Aldrich - O1014

Amino Acid Sequence
Phe-Cys-Phe-Trp-Lys-Thr-Cys-Thr-ol [Disulfide bridge: 2-7]
Biochem/physiol Actions
Somatostatin analog that is 3-times more potent than the native hormone in inhibiting the secretion of growth hormone.