2-[(5S,11S,14S)-11-(3-carbamimidamidopropyl)-14-methyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-5-yl]acetic acid

• ChemBase ID: 155608
• Molecular Formular: C23H32N8O7
• Molecular Mass: 532.54958
• Monoisotopic Mass: 532.2393954
• SMILES: C[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)NCc2cccc(c2)C(=O)N1)CC(=O)O)CCCNC(=N)N
• Canonical SMILES: NC(=N)NCCC[C@@H]1NC(=O)[C@H](C)NC(=O)c2cccc(c2)CNC(=O)[C@@H](NC(=O)CNC1=O)CC(=O)O
• InChI: InChI=1S/C23H32N8O7/c1-12-19(35)31-15(6-3-7-26-23(24)25)21(37)28-11-17(32)30-16(9-18(33)34)22(38)27-10-13-4-2-5-14(8-13)20(36)29-12/h2,4-5,8,12,15-16H,3,6-7,9-11H2,1H3,(H,27,38)(H,28,37)(H,29,36)(H,30,32)(H,31,35)(H,33,34)(H4,24,25,26)/t12-,15-,16-/m0/s1
• InChIKey: HRASXYOWQQTBAQ-RCBQFDQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5S,11S,14S)-11-(3-carbamimidamidopropyl)-14-methyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-5-yl]acetic acid
• IUPAC Traditional name: [(5S,11S,14S)-11-(3-carbamimidamidopropyl)-14-methyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-5-yl]acetic acid
• Synonyms: XJ735; Cyclo(Ala-Arg-Gly-Asp-3-Aminomethylbenzoyl)

Database IDs

• CAS Number: 153381-95-4
• MDL Number: MFCD11046000
• PubChem SID: 162249746
• PubChem CID: 71312170

CALCULATED PROPERTIES

• Acid pKa: 3.5370579
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -5.116934
• LogD (pH = 7.4): -5.1133304
• Log P: -5.1132526
• Molar Refractivity: 142.7446 cm^3
• Polarizability: 50.513756 Å^3
• Polar Surface Area: 244.7 Å^2
• Rotatable Bonds: 6
• 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 ... NPY(4852)

Product Information

• Purity: ≥96% (HPLC)
• Empirical Formula (Hill Notation): C23H32N8O7

DETAILS

Sigma Aldrich - C9357

Amino Acid Sequence
Ala-Arg-Gly-Asp-3-Aminomethylbenzoyl
Biochem/physiol Actions
Antagonist of RGD peptidomimetic αVβ3 integrin containing both anionic and cationic binding sites that straddle the RGD binding domain.
Cyclo(Ala-Arg-Gly-Asp-3-Aminomethylbenzoyl) (XJ735) is an RGD containing cyclic peptide (peptidomimetic) used as an antagonist specific to integrin αvβ3. XJ735 is used to study the role of integrin αvβ3 in cell-matrix interactions and processes.