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

• ChemBase ID: 131387
• Molecular Formular: C30H38ClN5O7S2
• Molecular Mass: 680.23502
• Monoisotopic Mass: 679.19011826
• SMILES: CC1([C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(SS1)(C)C)C(=O)O)Cc1ccc(cc1)Cl)NC(=O)[C@H](Cc1ccc(cc1)O)N)C
• Canonical SMILES: Oc1ccc(cc1)C[C@@H](C(=O)N[C@H]1C(=O)NCC(=O)N[C@@H](Cc2ccc(cc2)Cl)C(=O)N[C@H](C(SSC1(C)C)(C)C)C(=O)O)N
• InChI: InChI=1S/C30H38ClN5O7S2/c1-29(2)23(35-25(39)20(32)13-16-7-11-19(37)12-8-16)27(41)33-15-22(38)34-21(14-17-5-9-18(31)10-6-17)26(40)36-24(28(42)43)30(3,4)45-44-29/h5-12,20-21,23-24,37H,13-15,32H2,1-4H3,(H,33,41)(H,34,38)(H,35,39)(H,36,40)(H,42,43)/t20-,21-,23-,24-/m0/s1
• InChIKey: VTVUYFFDQHWCTJ-WMIMKTLMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,7S,13S)-13-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-7-[(4-chlorophenyl)methyl]-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-[(4-chlorophenyl)methyl]-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid
• Synonyms: [pCl-Phe4]-DPDPE; [D-Pen2,5, p-Cl-Phe4]-Enkephalin

Database IDs

• CAS Number: 122507-47-5
• MDL Number: MFCD00080350
• PubChem SID: 162225665
• PubChem CID: 159564

CALCULATED PROPERTIES

• Acid pKa: 3.2922864
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -0.411854
• LogD (pH = 7.4): -0.5657047
• Log P: -0.4155536
• Molar Refractivity: 172.8759 cm^3
• Polarizability: 67.9766 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

Pharmacology Properties

• Gene Information: human ... OPRD1(4985)mouse ... OPRD1(18386)rat ... OPRD1(24613)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - E6264

Amino Acid Sequence
Tyr-D-Pen-Gly-p-Chloro-Phe-D-Pen [Disulfide Bridge: 2-5]
Biochem/physiol Actions
Selective agonist at the δ opioid receptor.