(4S,7S,13S)-13-[(2S)-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: 155485
• Molecular Formular: C30H39N5O7S2
• Molecular Mass: 645.78996
• Monoisotopic Mass: 645.22909061
• SMILES: CC1([C@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](C(SS1)(C)C)C(=O)O)Cc1ccccc1)NC(=O)[C@H](Cc1ccc(cc1)O)N)C
• Canonical SMILES: O=C1CNC(=O)[C@H](NC(=O)[C@H](Cc2ccc(cc2)O)N)C(C)(C)SSC([C@@H](NC(=O)[C@H](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)/t20-,21-,23-,24-/m0/s1
• InChIKey: MCMMCRYPQBNCPH-WMIMKTLMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,7S,13S)-13-[(2S)-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: (4S,7S,13S)-13-[(2S)-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: DPDPE; [D-Pen2,5]-Enkephalin hydrate

Database IDs

• MDL Number: MFCD00076430
• PubChem SID: 162249623
• PubChem CID: 104787

CALCULATED PROPERTIES

• 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
• Polarizability: 66.06673 Å^3
• Polar Surface Area: 199.95 Å^2
• Rotatable Bonds: 7
• 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: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C30H39N5O7S2 · xH2O

DETAILS

Sigma Aldrich - E3888

Amino Acid Sequence
Tyr-Pen-Gly-Phe-Pen [Disulfide Bridge: 2-5]
Biochem/physiol Actions
Antinociceptive activity mediated through the δ1 receptor while the modulatory activity is mediated through the δ2 receptor. Tritiated [D-Pen2,5]-enkephalin is used as a δ1 ligand.