2-({1-[5-benzyl-8-(2-carbamoylethyl)-11-(carbamoylmethyl)-2-[(4-hydroxyphenyl)methyl]-3,6,9,12,20-pentaoxo-1,4,7,10,13-pentaazacycloicosane-14-carbonyl]pyrrolidin-2-yl}formamido)-5-carbamimidamido-N-(carbamoylmethyl)pentanamide

• ChemBase ID: 103821
• Molecular Formular: C48H68N14O12
• Molecular Mass: 1033.14012
• Monoisotopic Mass: 1032.51411369
• SMILES: NC(=N)NCCCC(NC(=O)C1CCCN1C(=O)C1CCCCCC(=O)NC(Cc2ccc(O)cc2)C(=O)NC(Cc2ccccc2)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)N)C(=O)N1)C(=O)NCC(=O)N
• Canonical SMILES: NC(=O)CC1NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(NC(=O)CCCCCC(NC1=O)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCNC(=N)N)Cc1ccc(cc1)O
• InChI: InChI=1S/C48H68N14O12/c49-37(64)20-19-31-42(69)61-35(25-38(50)65)45(72)59-32(47(74)62-22-8-13-36(62)46(73)58-30(12-7-21-54-48(52)53)41(68)55-26-39(51)66)11-5-2-6-14-40(67)56-33(24-28-15-17-29(63)18-16-28)43(70)60-34(44(71)57-31)23-27-9-3-1-4-10-27/h1,3-4,9-10,15-18,30-36,63H,2,5-8,11-14,19-26H2,(H2,49,64)(H2,50,65)(H2,51,66)(H,55,68)(H,56,67)(H,57,71)(H,58,73)(H,59,72)(H,60,70)(H,61,69)(H4,52,53,54)
• InChIKey: RNZNNGJIIRKABQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({1-[5-benzyl-8-(2-carbamoylethyl)-11-(carbamoylmethyl)-2-[(4-hydroxyphenyl)methyl]-3,6,9,12,20-pentaoxo-1,4,7,10,13-pentaazacycloicosane-14-carbonyl]pyrrolidin-2-yl}formamido)-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: 2-({1-[5-benzyl-8-(2-carbamoylethyl)-11-(carbamoylmethyl)-2-[(4-hydroxyphenyl)methyl]-3,6,9,12,20-pentaoxo-1,4,7,10,13-pentaazacycloicosane-14-carbonyl]pyrrolidin-2-yl}formamido)-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• Synonyms: Tyr-Phe-Gln-Asn-Asu-Pro-Arg-Gly-NH₂; [Asu^1,6,Arg^8]-VASOPRESSIN; [Asu1,6, Arg8]-Vasopressin

Database IDs

• CAS Number: 40944-53-4
• MDL Number: MFCD00133943
• PubChem SID: 162090881
• PubChem CID: 168160

CALCULATED PROPERTIES

• Acid pKa: 9.498462
• H Acceptors: 15
• H Donor: 14
• LogD (pH = 5.5): -7.335095
• LogD (pH = 7.4): -7.0583644
• Log P: -5.402244
• Molar Refractivity: 273.1049 cm^3
• Polarizability: 101.98032 Å^3
• Polar Surface Area: 435.41 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H332
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

DETAILS

MP Biomedicals - 02152964

Contains bond between Tyr and Asu.
An analog of arginine vasopressin.

Sigma Aldrich - V6254

Amino Acid Sequence
Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly [Disulfide Bridge: 1-6]

REFERENCES

• Hase, S., et al., J. Am. Chem. Soc., 94: 3590, (1972).