13-[2-amino-3-(4-hydroxyphenyl)propanamido]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid

• ChemBase ID: 103366
• Molecular Formular: C30H39N5O7S2
• Molecular Mass: 645.78996
• Monoisotopic Mass: 645.22909061
• SMILES: CC1(C)SSC(C)(C)C(NC(=O)C(N)Cc2ccc(O)cc2)C(=O)NCC(=O)NC(Cc2ccccc2)C(=O)NC1C(=O)O
• Canonical SMILES: O=C1CNC(=O)C(NC(=O)C(Cc2ccc(cc2)O)N)C(C)(C)SSC(C(NC(=O)C(N1)Cc1ccccc1)C(=O)O)(C)C
• InChI: InChI=1S/C30H39N5O7S2/c1-29(2)23(34-25(38)20(31)14-18-10-12-19(36)13-11-18)27(40)32-16-22(37)33-21(15-17-8-6-5-7-9-17)26(39)35-24(28(41)42)30(3,4)44-43-29/h5-13,20-21,23-24,36H,14-16,31H2,1-4H3,(H,32,40)(H,33,37)(H,34,38)(H,35,39)(H,41,42)
• InChIKey: MCMMCRYPQBNCPH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-[2-amino-3-(4-hydroxyphenyl)propanamido]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid
• IUPAC Traditional name: 13-[2-amino-3-(4-hydroxyphenyl)propanamido]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid
• Synonyms: Tyr-D-Pen-Gly-Phe-D-Pen; [D-Pen^2,5]-ENKEPHALIN

Database IDs

• CAS Number: 88373-73-3
• PubChem SID: 162090675
• PubChem CID: 14679811

CALCULATED PROPERTIES

• Polarizability: 66.06673 Å^3
• Polar Surface Area: 199.95 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false
• Acid pKa: 3.3853018
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -1.0157453
• LogD (pH = 7.4): -1.1687614
• Log P: -1.0190731
• Molar Refractivity: 168.0711 cm^3

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02151510

An analog with increased δ-receptor activity.

REFERENCES

• Mosberg, H.I., et al., Proc. Natl. Acad. Sci. USA, 80: 5871 (1983).