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

• ChemBase ID: 133295
• Molecular Formular: C46H65N13O11S2
• Molecular Mass: 1040.2188
• Monoisotopic Mass: 1039.43679197
• SMILES: CC(C)[C@H]1C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1)Cc1ccccc1)Cc1ccc(cc1)O)C(=O)N1CCC[C@H]1C(=O)N[C@H](CCCNC(=N)N)C(=O)NCC(=O)N)CC(=O)N
• Canonical SMILES: NC(=N)NCCC[C@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSCCC(=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)C(C)C)Cc1ccccc1
• InChI: InChI=1S/C46H65N13O11S2/c1-25(2)38-44(69)56-32(22-35(47)61)41(66)57-33(45(70)59-18-7-11-34(59)43(68)54-29(10-6-17-51-46(49)50)39(64)52-23-36(48)62)24-72-71-19-16-37(63)53-30(21-27-12-14-28(60)15-13-27)40(65)55-31(42(67)58-38)20-26-8-4-3-5-9-26/h3-5,8-9,12-15,25,29-34,38,60H,6-7,10-11,16-24H2,1-2H3,(H2,47,61)(H2,48,62)(H,52,64)(H,53,63)(H,54,68)(H,55,65)(H,56,69)(H,57,66)(H,58,67)(H4,49,50,51)/t29-,30+,31+,32+,33+,34+,38+/m1/s1
• InChIKey: KEBRFHAVFOSSOX-WSFLLCRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(2S)-1-[(4R,7S,10S,13S,16S)-13-benzyl-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-10-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: (2R)-2-{[(2S)-1-[(4R,7S,10S,13S,16S)-13-benzyl-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-10-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• Synonyms: Val4-dDAVP; [deamino-Cys1, Val4, D-Arg8]-Vasopressin

Database IDs

• MDL Number: MFCD00080166
• PubChem SID: 162227572
• PubChem CID: 44419026

CALCULATED PROPERTIES

• Acid pKa: 9.497647
• H Acceptors: 14
• H Donor: 13
• LogD (pH = 5.5): -6.0114813
• LogD (pH = 7.4): -5.734285
• Log P: -4.0801163
• Molar Refractivity: 276.1629 cm^3
• Polarizability: 103.21037 Å^3
• Polar Surface Area: 392.32 Å^2
• Rotatable Bonds: 17
• 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 ... AVPR2(554)mouse ... AVPR2(12000)rat ... AVPR2(25108)

Product Information

• Purity: ≥95%

DETAILS

Sigma Aldrich - V2013

Amino Acid Sequence
Mpa-Tyr-Phe-Val-Asn-Cys-Pro-Arg-Gly-NH2
Biochem/physiol Actions
Selective V2 vasopressin receptor agonist.