(2S)-6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13,16-dibenzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide

• ChemBase ID: 127393
• Molecular Formular: C46H65N13O11S2
• Molecular Mass: 1040.2188
• Monoisotopic Mass: 1039.43679197
• SMILES: NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1NC(=O)[C@@H](NC(=O)[C@@H](CCC(=O)N)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@@H](N)CSSC1)CC(=O)N
• Canonical SMILES: NCCCC[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1CSSC[C@H](N)C(=O)N[C@H](Cc2ccccc2)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)CCC(=O)N)Cc1ccccc1
• InChI: InChI=1S/C46H65N13O11S2/c47-18-8-7-14-29(40(64)52-23-38(51)62)54-45(69)35-15-9-19-59(35)46(70)34-25-72-71-24-28(48)39(63)55-31(20-26-10-3-1-4-11-26)43(67)56-32(21-27-12-5-2-6-13-27)42(66)53-30(16-17-36(49)60)41(65)57-33(22-37(50)61)44(68)58-34/h1-6,10-13,28-35H,7-9,14-25,47-48H2,(H2,49,60)(H2,50,61)(H2,51,62)(H,52,64)(H,53,66)(H,54,69)(H,55,63)(H,56,67)(H,57,65)(H,58,68)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
• InChIKey: SFKQVVDKFKYTNA-DZCXQCEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13,16-dibenzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide
• IUPAC Traditional name: felypressin
• Synonyms: 2-L-Phenylalanine-8-L-lysinevasopressin; 2,3-Bis(phenylalanine)-8-lysineoxytocin; 2-(Phenylalanine)-8-lysinevasopressin; 2-Phenylalanine-8-lysine-vasopressin; Felypressin; Octapressin; PLV 2; Phelypressin; Felypressin

Database IDs

• CAS Number: 56-59-7
• PubChem SID: 162221714
• PubChem CID: 5956; 14257662
• CHEBI ID: 60564
• CHEMBL: 1697764
• Chemspider ID: 16736539
• DrugBank ID: DB00093
• Unique Ingredient Identifier: 17N2918V6G
• Wikipedia Title: Felypressin

CALCULATED PROPERTIES

• Acid pKa: 11.38535
• H Acceptors: 13
• H Donor: 12
• LogD (pH = 5.5): -10.749746
• LogD (pH = 7.4): -8.668554
• Log P: -5.8353696
• Molar Refractivity: 264.7915 cm^3
• Polarizability: 103.83951 Å^3
• Polar Surface Area: 405.32 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F245200

Felypressin(Octapressin) is a vasopressin 1 agonist and a peptide containing eight amino acids including cystine. Felypressin is used as a vasoconstrictor.

REFERENCES

• Boissonnas, G., et al.: Helv. Chim. Acta, 43, 190 (1960)
• Farkas, D., et al.: Curr. Drug Metab., 6, 111 (1960)
• Elferink, M., et al.: Toxicol. Appl. Pharmacol., 229, 300 (1960)