(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid

• ChemBase ID: 153607
• Molecular Formular: C40H54N8O8
• Molecular Mass: 774.90556
• Monoisotopic Mass: 774.40646073
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](C(C)C)N
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)O)Cc1ccccc1)Cc1nc[nH]c1)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)N)Cc1ccc(cc1)O)C
• InChI: InChI=1S/C40H54N8O8/c1-5-24(4)34(47-35(50)29(44-37(52)33(41)23(2)3)18-26-13-15-28(49)16-14-26)38(53)45-30(20-27-21-42-22-43-27)39(54)48-17-9-12-32(48)36(51)46-31(40(55)56)19-25-10-7-6-8-11-25/h6-8,10-11,13-16,21-24,29-34,49H,5,9,12,17-20,41H2,1-4H3,(H,42,43)(H,44,52)(H,45,53)(H,46,51)(H,47,50)(H,55,56)/t24-,29-,30-,31-,32-,33-,34-/m0/s1
• InChIKey: QSBGWDDCOJYQGY-KOQODJNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
• Synonyms: [des-Arg1]-Angiotensin III; Ang IV; Angiotensin II (3-8); Angiotensin IV trifluoroacetate salt

Database IDs

• CAS Number: 12676-15-2(freebase)
• MDL Number: MFCD00167496
• PubChem SID: 162247746
• PubChem CID: 123814

CALCULATED PROPERTIES

• Acid pKa: 3.5196147
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -1.1983631
• LogD (pH = 7.4): -0.48865023
• Log P: -0.5180567
• Molar Refractivity: 205.4805 cm^3
• Polarizability: 80.406 Å^3
• Polar Surface Area: 248.94 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ~1 mg/mL
• Apperance: lyophilized powder; white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C40H54N8O8; C40H54N8O8 · xC2HF3O2

DETAILS

Sigma Aldrich - A0230

Amino Acid Sequence
Val-Tyr-Ile-His-Pro-Phe
Biochem/physiol Actions
AT4 angiotensin receptor agonist. The AT4 receptor appears to be important in synaptic plasticity and thus in learning and memory.

Sigma Aldrich - A1599

Amino Acid Sequence
Val-Tyr-Ile-His-Pro-Phe