2-({1-[13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-methoxyphenyl)methyl]-20,20-dimethyl-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

• ChemBase ID: 103822
• Molecular Formular: C49H70N14O12S2
• Molecular Mass: 1111.2967
• Monoisotopic Mass: 1110.47390575
• SMILES: COc1ccc(CC2NC(=O)CC(C)(C)SSCC(NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(Cc3ccccc3)NC2=O)C(=O)N2CCCC2C(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)N)cc1
• Canonical SMILES: COc1ccc(cc1)CC1NC(=O)CC(C)(C)SSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)Cc1ccccc1)CCC(=O)N)CC(=O)N)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCNC(=N)N
• InChI: InChI=1S/C49H70N14O12S2/c1-49(2)24-40(67)57-32(22-28-13-15-29(75-3)16-14-28)43(70)60-33(21-27-9-5-4-6-10-27)44(71)58-31(17-18-37(50)64)42(69)61-34(23-38(51)65)45(72)62-35(26-76-77-49)47(74)63-20-8-12-36(63)46(73)59-30(11-7-19-55-48(53)54)41(68)56-25-39(52)66/h4-6,9-10,13-16,30-36H,7-8,11-12,17-26H2,1-3H3,(H2,50,64)(H2,51,65)(H2,52,66)(H,56,68)(H,57,67)(H,58,71)(H,59,73)(H,60,70)(H,61,69)(H,62,72)(H4,53,54,55)
• InChIKey: HNOGCDKPALYUIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({1-[13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-methoxyphenyl)methyl]-20,20-dimethyl-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
• IUPAC Traditional name: 2-({1-[13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-methoxyphenyl)methyl]-20,20-dimethyl-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: [deamino-Pen1, O-Me-Tyr2, Arg8]-Vasopressin; 3-Mercapto-3-methylbutyryl-Tyr[O-Methyl]-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH₂; [Deamino-Pen^1,O-Me-Tyr^2,Arg^8]-VASOPRESSIN

Database IDs

• CAS Number: 67269-08-3
• MDL Number: MFCD00076745
• PubChem SID: 162103284; 24900721
• PubChem CID: 119517

CALCULATED PROPERTIES

• Acid pKa: 11.267652
• H Acceptors: 15
• H Donor: 13
• LogD (pH = 5.5): -7.2725616
• LogD (pH = 7.4): -7.262874
• Log P: -5.5173593
• Molar Refractivity: 293.2636 cm^3
• Polarizability: 110.05094 Å^3
• Polar Surface Area: 424.41 Å^2
• Rotatable Bonds: 20
• 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

Pharmacology Properties

• Gene Information: human ... AVPI1(60370)mouse ... AVPI1(69534)rat ... AVPI1(171386), LOC689723(689723)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 02152967

Contains disulfide bond between 3-mercapto group and Cys.

Sigma Aldrich - V1880

Amino Acid Sequence
3-Mercapto-3-methylbutyryl-Tyr-OMet-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
Potent V1 (vasopressor) antagonist with low antidiuretic activity.