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

• ChemBase ID: 128743
• Molecular Formular: C45H63N13O12S2
• Molecular Mass: 1042.19162
• Monoisotopic Mass: 1041.41605652
• SMILES: NC(=O)CNC(=O)[C@H](CCCN)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](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC1)CC(=O)N
• Canonical SMILES: NCCC[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1CSSC[C@H](N)C(=O)N[C@H](Cc2ccc(cc2)O)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/C45H63N13O12S2/c46-16-4-8-28(39(64)51-21-37(50)62)53-44(69)34-9-5-17-58(34)45(70)33-23-72-71-22-27(47)38(63)54-30(19-25-10-12-26(59)13-11-25)42(67)55-31(18-24-6-2-1-3-7-24)41(66)52-29(14-15-35(48)60)40(65)56-32(20-36(49)61)43(68)57-33/h1-3,6-7,10-13,27-34,59H,4-5,8-9,14-23,46-47H2,(H2,48,60)(H2,49,61)(H2,50,62)(H,51,64)(H,52,66)(H,53,69)(H,54,63)(H,55,67)(H,56,65)(H,57,68)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
• InChIKey: MUNMIGOEDGHVLE-LGYYRGKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: ornipressin
• Synonyms: 8-L-Ornithine-vasopressin; Orn8-vasopressin; Ornipressin; Ornithine-vasopressin; POR 8; [8-Ornithine]vasopressin; Ornipressin

Database IDs

• CAS Number: 3397-23-7
• PubChem SID: 162223049
• PubChem CID: 14257660
• ATC CODE: H01BA05
• Chemspider ID: 16736525
• MeSH Name: Ornipressin
• Wikipedia Title: Ornipressin

CALCULATED PROPERTIES

• Acid pKa: 9.254841
• H Acceptors: 14
• H Donor: 13
• LogD (pH = 5.5): -11.467028
• LogD (pH = 7.4): -8.915116
• Log P: -7.0813503
• Molar Refractivity: 262.1714 cm^3
• Polarizability: 102.6616 Å^3
• Polar Surface Area: 425.55 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O688800

Ornipressin is an analogue of Vasopressin. Ornipressin is used as a vasoconstrictor, haemostatic and renal agent.

REFERENCES

• Fruhstofer, H. et al.: Br. J. Anaesth., 73, 220 (1994)
• De Kock, M. et al.: Aneth. Analg., 90, 1301 (1994)
• Nolte, H. et al.: Anaethesist, 21, 398 (1994)