(2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-13-(carbamoylmethyl)-22-[(4-ethoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-16-(propan-2-yl)-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide

• ChemBase ID: 134347
• Molecular Formular: C53H77N13O11S2
• Molecular Mass: 1136.38898
• Monoisotopic Mass: 1135.53069235
• SMILES: CCOc1ccc(cc1)C[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC2(CCCCC2)CC(=O)N1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N)CC(=O)N)C(C)C)Cc1ccccc1
• Canonical SMILES: CCOc1ccc(cc1)C[C@@H]1NC(=O)CC2(CCCCC2)SSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccccc1)C(C)C)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCNC(=N)N
• InChI: InChI=1S/C53H77N13O11S2/c1-4-77-34-19-17-33(18-20-34)26-36-46(71)62-37(25-32-13-7-5-8-14-32)48(73)65-44(31(2)3)50(75)63-38(27-41(54)67)47(72)64-39(30-78-79-53(28-43(69)60-36)21-9-6-10-22-53)51(76)66-24-12-16-40(66)49(74)61-35(15-11-23-58-52(56)57)45(70)59-29-42(55)68/h5,7-8,13-14,17-20,31,35-40,44H,4,6,9-12,15-16,21-30H2,1-3H3,(H2,54,67)(H2,55,68)(H,59,70)(H,60,69)(H,61,74)(H,62,71)(H,63,75)(H,64,72)(H,65,73)(H4,56,57,58)/t35-,36-,37-,38-,39-,40-,44-/m0/s1
• InChIKey: SDFJYGJKEXYVCG-ZZTMPEIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-13-(carbamoylmethyl)-22-[(4-ethoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-16-(propan-2-yl)-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-13-(carbamoylmethyl)-22-[(4-ethoxyphenyl)methyl]-16-isopropyl-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• Synonyms: [β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Et-Tyr2, Val4, Arg8]-Vasopressin

Database IDs

• CAS Number: 77453-01-1
• MDL Number: MFCD00076752
• PubChem SID: 162228623
• PubChem CID: 9963507

CALCULATED PROPERTIES

• Acid pKa: 11.301616
• H Acceptors: 14
• H Donor: 12
• LogD (pH = 5.5): -3.8422856
• LogD (pH = 7.4): -3.833208
• Log P: -2.1002018
• Molar Refractivity: 306.242 cm^3
• Polarizability: 115.37771 Å^3
• Polar Surface Area: 381.32 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

Pharmacology Properties

• Gene Information: human ... AVPR1A(552), AVPR2(554), OXT(5020), OXTR(5021)mouse ... AVPR1A(54140), AVPR2(12000)rat ... AVPR1A(25107), AVPR2(25108), OXT(18429), OXTR(18430)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - V4253

Amino Acid Sequence
(1-Mercaptocyclohexyl)acetyl-Tyr(O-Ethyl)-Phe-Val-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
Potent V1a and V2 vasopressin receptor and oxytocin receptor antagonist.