(2S,3R)-2-{[(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(3-aminopropyl)-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]formamido}-3-hydroxybutanamide

• ChemBase ID: 134090
• Molecular Formular: C50H67N11O11S2
• Molecular Mass: 1062.26408
• Monoisotopic Mass: 1061.44629402
• SMILES: C[C@H]([C@H]1C(=O)N[C@@H](C(SSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCN)Cc1c[nH]c2c1cccc2)Cc1ccc(cc1)O)NC(=O)[C@@H](Cc1ccccc1)N)(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N)O
• Canonical SMILES: NCCC[C@@H]1NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](CSSC([C@H](NC(=O)[C@@H](NC1=O)[C@H](O)C)C(=O)N[C@H](C(=O)N)[C@H](O)C)(C)C)NC(=O)[C@@H](Cc1ccccc1)N)Cc1ccc(cc1)O)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C50H67N11O11S2/c1-26(62)39(42(53)65)59-49(72)41-50(3,4)74-73-25-38(58-43(66)33(52)21-28-11-6-5-7-12-28)47(70)56-36(22-29-16-18-31(64)19-17-29)45(68)57-37(23-30-24-54-34-14-9-8-13-32(30)34)46(69)55-35(15-10-20-51)44(67)60-40(27(2)63)48(71)61-41/h5-9,11-14,16-19,24,26-27,33,35-41,54,62-64H,10,15,20-23,25,51-52H2,1-4H3,(H2,53,65)(H,55,69)(H,56,70)(H,57,68)(H,58,66)(H,59,72)(H,60,67)(H,61,71)/t26-,27-,33-,35+,36+,37-,38+,39+,40+,41-/m1/s1
• InChIKey: PZWWYAHWHHNCHO-FGHAYEPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-{[(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(3-aminopropyl)-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]formamido}-3-hydroxybutanamide
• IUPAC Traditional name: (2S,3R)-2-{[(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(3-aminopropyl)-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]formamido}-3-hydroxybutanamide
• Synonyms: CTOP

Database IDs

• CAS Number: 103429-31-8
• MDL Number: MFCD00076708
• PubChem SID: 162228367
• PubChem CID: 5311058

CALCULATED PROPERTIES

• Acid pKa: 9.254615
• H Acceptors: 13
• H Donor: 14
• LogD (pH = 5.5): -6.6993213
• LogD (pH = 7.4): -4.136709
• Log P: -2.2762504
• Molar Refractivity: 277.7301 cm^3
• Polarizability: 110.06569 Å^3
• Polar Surface Area: 375.31 Å^2
• Rotatable Bonds: 16
• 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

Pharmacology Properties

• Gene Information: mouse ... Pnoc(18155)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - P5296

Amino Acid Sequence
Phe-Cys-Tyr-Trp-Orn-Thr-Pen-Thr-NH2 [Disulfide Bridge: 2-7]
Biochem/physiol Actions
Selective ligand for μ-opioid receptors.
Linkage
Somatostatin analog