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

• ChemBase ID: 133967
• Molecular Formular: C81H113N19O19S2
• Molecular Mass: 1721.00982
• Monoisotopic Mass: 1719.79015449
• SMILES: C[C@H]([C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[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)Cc1ccccc1)CC(=O)N)CCCCN)NC(=O)[C@@H]1CCCN1)C(=O)N[C@@H](CCCCN)C(=O)O)CO)CO)Cc1ccccc1)O
• Canonical SMILES: NCCCC[C@@H](C(=O)O)NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@@H]2CCCN2)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CO)CO)Cc1ccccc1)[C@H](O)C)CCCCN)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C81H113N19O19S2/c1-46(103)67-80(117)95-59(38-49-24-9-4-10-25-49)73(110)96-62(42-101)76(113)97-63(43-102)77(114)99-65(79(116)90-56(81(118)119)30-15-18-34-84)45-121-120-44-64(98-68(105)53-31-19-35-86-53)78(115)89-54(28-13-16-32-82)69(106)94-61(40-66(85)104)75(112)92-57(36-47-20-5-2-6-21-47)71(108)91-58(37-48-22-7-3-8-23-48)72(109)93-60(39-50-41-87-52-27-12-11-26-51(50)52)74(111)88-55(70(107)100-67)29-14-17-33-83/h2-12,20-27,41,46,53-65,67,86-87,101-103H,13-19,28-40,42-45,82-84H2,1H3,(H2,85,104)(H,88,111)(H,89,115)(H,90,116)(H,91,108)(H,92,112)(H,93,109)(H,94,106)(H,95,117)(H,96,110)(H,97,113)(H,98,105)(H,99,114)(H,100,107)(H,118,119)/t46-,53+,54+,55+,56+,57+,58+,59+,60+,61+,62+,63+,64+,65+,67+/m1/s1
• InChIKey: DDRPLNQJNRBRNY-WYYADCIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-{[(4R,7S,10S,13S,16S,19S,22S,25S,28S,31S,34S,37R)-19,34-bis(4-aminobutyl)-13,25,28-tribenzyl-31-(carbamoylmethyl)-16-[(1R)-1-hydroxyethyl]-7,10-bis(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-37-[(2S)-pyrrolidine-2-amido]-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontan-4-yl]formamido}hexanoic acid
• IUPAC Traditional name: (2S)-6-amino-2-{[(4R,7S,10S,13S,16S,19S,22S,25S,28S,31S,34S,37R)-19,34-bis(4-aminobutyl)-13,25,28-tribenzyl-31-(carbamoylmethyl)-16-[(1R)-1-hydroxyethyl]-7,10-bis(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-37-[(2S)-pyrrolidine-2-amido]-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontan-4-yl]formamido}hexanoic acid
• Synonyms: CST-14; Pro-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Ser-Ser-Cys-Lys [Disulfide bridge: 2–13]; Cortistatin-14

Database IDs

• CAS Number: 186901-48-4
• MDL Number: MFCD01075120
• PubChem SID: 162228244
• PubChem CID: 16133803

CALCULATED PROPERTIES

• Acid pKa: 3.3097928
• H Acceptors: 23
• H Donor: 23
• LogD (pH = 5.5): -16.608707
• LogD (pH = 7.4): -14.366776
• Log P: -7.9703474
• Molar Refractivity: 445.2143 cm^3
• Polarizability: 175.95757 Å^3
• Polar Surface Area: 625.26 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

PROPERTIES

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: ≥97% (HPLC)
• Packaging: vial of 0.5 mg

DETAILS

Sigma Aldrich - C5808

Biochem/physiol Actions
Somatostatin-like neuropeptide with neuronal depressant and sleep modulating properties. Exogenous cortistatin impairs short-term memory processing.1