(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-3-phenylpropanamido]hexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid

• ChemBase ID: 132989
• Molecular Formular: C74H115N21O17
• Molecular Mass: 1570.8354
• Monoisotopic Mass: 1569.87798133
• SMILES: C[C@H]([C@@H](C(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)[C@H](O)C)C(C)C)C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N)CC(C)C)CCCNC(=N)N)CCCNC(=N)N)CCC(=O)N)Cc1ccccc1
• InChI: InChI=1S/C74H115N21O17/c1-40(2)34-53(91-68(107)54(36-44-18-10-8-11-19-44)86-58(100)39-84-57(99)38-85-62(101)48(76)35-46-25-27-47(97)28-26-46)67(106)89-51(24-17-33-83-74(80)81)63(102)87-50(23-16-32-82-73(78)79)64(103)90-52(29-30-56(77)98)65(104)92-55(37-45-20-12-9-13-21-45)69(108)88-49(22-14-15-31-75)66(105)93-59(41(3)4)70(109)94-60(42(5)6)71(110)95-61(43(7)96)72(111)112/h8-13,18-21,25-28,40-43,48-55,59-61,96-97H,14-17,22-24,29-39,75-76H2,1-7H3,(H2,77,98)(H,84,99)(H,85,101)(H,86,100)(H,87,102)(H,88,108)(H,89,106)(H,90,103)(H,91,107)(H,92,104)(H,93,105)(H,94,109)(H,95,110)(H,111,112)(H4,78,79,82)(H4,80,81,83)/t43-,48+,49+,50+,51+,52+,53+,54+,55+,59+,60+,61+/m1/s1
• InChIKey: AGTSSZRZBSNTGQ-ITZCFHCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-3-phenylpropanamido]hexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid
• IUPAC Traditional name: (2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-3-phenylpropanamido]hexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid
• Synonyms: Prodynorphin 228-240; Rimorphin; Dynorphin B porcine

Database IDs

• CAS Number: 85006-82-2
• MDL Number: MFCD00076372
• PubChem SID: 162227266
• PubChem CID: 25075991

CALCULATED PROPERTIES

• Acid pKa: -1.3101517
• H Acceptors: 25
• H Donor: 24
• LogD (pH = 5.5): -13.462449
• LogD (pH = 7.4): -11.362707
• Log P: -8.043679
• Molar Refractivity: 429.3199 cm^3
• Polarizability: 159.4686 Å^3
• Polar Surface Area: 645.89 Å^2
• Rotatable Bonds: 51
• 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: pig ... PDYN(445529)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - D1398

Amino Acid Sequence
Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Gln-Phe-Lys-Val-Val-Thr
Biochem/physiol Actions
Endogenous κ1b opioid receptor agonist.