(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-4-methylpentanamido]-3-phenylpropanamido]-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]pentanediamide

• ChemBase ID: 132798
• Molecular Formular: C54H76N14O10
• Molecular Mass: 1081.26904
• Monoisotopic Mass: 1080.5868847
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)[C@H](Cc1ccccc1)N
• Canonical SMILES: NC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CCCNC(=N)N)CCC(=O)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)N)CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C54H76N14O10/c1-32(2)28-41(66-47(72)36(55)29-33-14-6-3-7-15-33)50(75)67-42(31-35-18-10-5-11-19-35)51(76)64-39(23-25-45(57)70)53(78)68-27-13-21-43(68)52(77)63-38(22-24-44(56)69)49(74)62-37(20-12-26-61-54(59)60)48(73)65-40(46(58)71)30-34-16-8-4-9-17-34/h3-11,14-19,32,36-43H,12-13,20-31,55H2,1-2H3,(H2,56,69)(H2,57,70)(H2,58,71)(H,62,74)(H,63,77)(H,64,76)(H,65,73)(H,66,72)(H,67,75)(H4,59,60,61)/t36-,37-,38-,39-,40-,41-,42-,43-/m0/s1
• InChIKey: HWYCFZUSOBOBIN-AQJXLSMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-4-methylpentanamido]-3-phenylpropanamido]-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]pentanediamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-4-methylpentanamido]-3-phenylpropanamido]-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]pentanediamide
• Synonyms: F-8-F-NH2; Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe amide

Database IDs

• CAS Number: 99566-27-5
• MDL Number: MFCD00076704
• PubChem SID: 162227075; 24897882
• PubChem CID: 9854861

CALCULATED PROPERTIES

• Acid pKa: 11.476593
• H Acceptors: 14
• H Donor: 13
• LogD (pH = 5.5): -6.4421473
• LogD (pH = 7.4): -4.766168
• Log P: -2.621044
• Molar Refractivity: 297.272 cm^3
• Polarizability: 111.82687 Å^3
• Polar Surface Area: 412.1 Å^2
• Rotatable Bonds: 32
• 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: rat ... Npffr1(64107)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - P3293

Biochem/physiol Actions
Attenuates analgesic effects of morphine
Other Notes
Endogenous peptide found in periaqueductal grey and in dorsal spinal cord