(2S)-N-[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-5-amino-1-carbamoylpentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}pyrrolidin-1-yl]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-carbamoylethyl]-2-[(2S)-2-[(2R)-3-(4-methoxyphenyl)-2-(2-phenylacetamido)propanamido]-3-phenylpropanamido]pentanediamide

• ChemBase ID: 155652
• Molecular Formular: C59H86N18O12
• Molecular Mass: 1239.42754
• Monoisotopic Mass: 1238.66726028
• SMILES: COc1ccc(cc1)C[C@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N)NC(=O)Cc1ccccc1
• Canonical SMILES: NCCCC[C@@H](C(=O)N)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)Cc1ccccc1)Cc1ccc(cc1)OC)Cc1ccccc1)CCC(=O)N)CC(=O)N)CCCNC(=N)N)CCCNC(=N)N
• InChI: InChI=1S/C59H86N18O12/c1-89-38-23-21-37(22-24-38)32-43(70-49(80)33-36-15-6-3-7-16-36)53(84)75-44(31-35-13-4-2-5-14-35)54(85)72-41(25-26-47(61)78)52(83)76-45(34-48(62)79)55(86)74-42(19-11-29-69-59(66)67)57(88)77-30-12-20-46(77)56(87)73-40(18-10-28-68-58(64)65)51(82)71-39(50(63)81)17-8-9-27-60/h2-7,13-16,21-24,39-46H,8-12,17-20,25-34,60H2,1H3,(H2,61,78)(H2,62,79)(H2,63,81)(H,70,80)(H,71,82)(H,72,85)(H,73,87)(H,74,86)(H,75,84)(H,76,83)(H4,64,65,68)(H4,66,67,69)/t39-,40-,41-,42-,43+,44-,45-,46-/m0/s1
• InChIKey: ARYIFIDWSDPRCG-LABPQDBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-5-amino-1-carbamoylpentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}pyrrolidin-1-yl]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-carbamoylethyl]-2-[(2S)-2-[(2R)-3-(4-methoxyphenyl)-2-(2-phenylacetamido)propanamido]-3-phenylpropanamido]pentanediamide
• IUPAC Traditional name: (2S)-N-[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-5-amino-1-carbamoylpentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}pyrrolidin-1-yl]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-carbamoylethyl]-2-[(2S)-2-[(2R)-3-(4-methoxyphenyl)-2-(2-phenylacetamido)propanamido]-3-phenylpropanamido]pentanediamide
• Synonyms: [Phenylacetyl1, O-Me-D-Tyr2, Arg6,8, Lys9]-Vasopressin amide

Database IDs

• MDL Number: MFCD00237315
• PubChem SID: 162249790
• PubChem CID: 71312187

CALCULATED PROPERTIES

• Acid pKa: 12.148964
• H Acceptors: 19
• H Donor: 17
• LogD (pH = 5.5): -12.476457
• LogD (pH = 7.4): -12.046418
• Log P: -5.207448
• Molar Refractivity: 345.5913 cm^3
• Polarizability: 126.014656 Å^3
• Polar Surface Area: 512.33 Å^2
• Rotatable Bonds: 39
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

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 ... AVPR1A(552)mouse ... AVPR1A(54140)rat ... AVPR1A(25107)

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C59H86N18O12

DETAILS

Sigma Aldrich - V2138

Amino Acid Sequence
Phenylac-MeTyr-Phe-Gln-Asn-Arg-Pro-Arg-Lys-NH2
Biochem/physiol Actions
Selective antagonist having an extremely high affinity for the V-1a vasopressin receptors.