(3S,6S,9S,12R,15S,18S)-9-(4-aminobutyl)-3-benzyl-15-[(4-hydroxyphenyl)methyl]-12-(1H-indol-3-ylmethyl)-1,18-dimethyl-6-(propan-2-yl)-1,4,7,10,13,16-hexaazacyclooctadecane-2,5,8,11,14,17-hexone

• ChemBase ID: 153123
• Molecular Formular: C44H56N8O7
• Molecular Mass: 808.96484
• Monoisotopic Mass: 808.42719617
• SMILES: C[C@H]1C(=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)N1C)Cc1ccccc1)C(C)C)CCCCN)Cc1c[nH]c2c1cccc2)Cc1ccc(cc1)O
• Canonical SMILES: NCCCC[C@H]1NC(=O)[C@@H](NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@@H](N(C(=O)[C@H](NC(=O)[C@@H](NC1=O)C(C)C)Cc1ccccc1)C)C)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C44H56N8O7/c1-26(2)38-43(58)50-37(23-28-12-6-5-7-13-28)44(59)52(4)27(3)39(54)48-35(22-29-17-19-31(53)20-18-29)41(56)49-36(24-30-25-46-33-15-9-8-14-32(30)33)42(57)47-34(40(55)51-38)16-10-11-21-45/h5-9,12-15,17-20,25-27,34-38,46,53H,10-11,16,21-24,45H2,1-4H3,(H,47,57)(H,48,54)(H,49,56)(H,50,58)(H,51,55)/t27-,34-,35-,36+,37-,38-/m0/s1
• InChIKey: NPJIOCBFOAHEDO-AVWFULIKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,12R,15S,18S)-9-(4-aminobutyl)-3-benzyl-15-[(4-hydroxyphenyl)methyl]-12-(1H-indol-3-ylmethyl)-1,18-dimethyl-6-(propan-2-yl)-1,4,7,10,13,16-hexaazacyclooctadecane-2,5,8,11,14,17-hexone
• IUPAC Traditional name: (3S,6S,9S,12R,15S,18S)-9-(4-aminobutyl)-3-benzyl-15-[(4-hydroxyphenyl)methyl]-12-(1H-indol-3-ylmethyl)-6-isopropyl-1,18-dimethyl-1,4,7,10,13,16-hexaazacyclooctadecane-2,5,8,11,14,17-hexone
• Synonyms: Cyclic(N-methyl-Ala-Tyr-D-Trp-Lys-Val-Phe); MK 678; Seglitide

Database IDs

• MDL Number: MFCD00872233
• PubChem SID: 24278692; 162247263
• PubChem CID: 5311430

CALCULATED PROPERTIES

• Acid pKa: 9.382595
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -0.49411798
• LogD (pH = 7.4): 0.059519157
• Log P: 1.5899932
• Molar Refractivity: 221.9133 cm^3
• Polarizability: 87.5762 Å^3
• Polar Surface Area: 227.85 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble26 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... SSTR1(6751), SSTR2(6752), SSTR3(6753), SSTR4(6754), SSTR5(6755)mouse ... Sstr3(20607)rat ... Sstr2(54305)

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C44H56N8O7

DETAILS

Sigma Aldrich - S1316

Amino Acid Sequence
NMe-Ala-Tyr-Trp-Lys-Val-Phe
Biochem/physiol Actions
Selective sst2 somatostatin receptor agonist.