(2R)-2-amino-3-{[(2R)-3-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(carbamoylmethyl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-2-[(2S)-3-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-oxopropyl]disulfanyl}propanoic acid; acetic acid

• ChemBase ID: 155210
• Molecular Formular: C30H50N12O12S2
• Molecular Mass: 834.9212
• Monoisotopic Mass: 834.3112571
• SMILES: CC(=O)O.C1C[C@H](N(C1)C(=O)[C@H](CSSC[C@@H](C(=O)O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N
• Canonical SMILES: NC(=O)C[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCNC(=N)N)CSSC[C@@H](C(=O)O)N)NC(=O)[C@@H]1CCC(=O)N1.CC(=O)O
• InChI: InChI=1S/C28H46N12O10S2.C2H4O2/c29-13(27(49)50)11-51-52-12-17(39-24(46)16(9-19(30)41)38-23(45)15-5-6-21(43)36-15)26(48)40-8-2-4-18(40)25(47)37-14(3-1-7-34-28(32)33)22(44)35-10-20(31)42;1-2(3)4/h13-18H,1-12,29H2,(H2,30,41)(H2,31,42)(H,35,44)(H,36,43)(H,37,47)(H,38,45)(H,39,46)(H,49,50)(H4,32,33,34);1H3,(H,3,4)/t13-,14-,15-,16-,17-,18-;/m0./s1
• InChIKey: JCYUTVYWHXRGEB-ANMSZRTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[(2R)-3-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(carbamoylmethyl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-2-[(2S)-3-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-oxopropyl]disulfanyl}propanoic acid; acetic acid
• IUPAC Traditional name: (2R)-2-amino-3-{[(2R)-3-[(2S)-2-{[(1S)-4-carbamimidamido-1-(carbamoylmethylcarbamoyl)butyl]carbamoyl}pyrrolidin-1-yl]-2-[(2S)-3-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-oxopropyl]disulfanyl}propanoic acid; acetic acid
• Synonyms: [pGlu4, (Cys2)6, Arg8]-Vasopressin Fragment 4-9 acetate salt

Database IDs

• CAS Number: 100930-16-3
• MDL Number: MFCD00133973
• PubChem SID: 162249348
• PubChem CID: 71312103

CALCULATED PROPERTIES

• Acid pKa: -1.0166963
• H Acceptors: 14
• H Donor: 12
• LogD (pH = 5.5): -12.388971
• LogD (pH = 7.4): -11.10673
• Log P: -9.575138
• Molar Refractivity: 195.2501 cm^3
• Polarizability: 72.216034 Å^3
• Polar Surface Area: 377.21 Å^2
• Rotatable Bonds: 22
• 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 ... AVP(551)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C28H46N12O10S2 · xC2H4O2

DETAILS

Sigma Aldrich - V0255

Amino Acid Sequence
pGlu-Asn-Cys(Cys)-Pro-Arg-Gly-NH2
Biochem/physiol Actions
A more potent neuropeptide than AVP with selective effects on memory and related processes.