2-[(2S,5R,8S,11S)-5-benzyl-11-{3-[(diaminomethylidene)amino]propyl}-7-methyl-3,6,9,12,15-pentaoxo-8-(propan-2-yl)-1,4,7,10,13-pentaazacyclopentadecan-2-yl]acetic acid

• ChemBase ID: 126595
• Molecular Formular: C27H40N8O7
• Molecular Mass: 588.6559
• Monoisotopic Mass: 588.30199566
• SMILES: O=C1N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C(=O)N(C)[C@H]1C(C)C)Cc1ccccc1)CC(=O)O)CCCN=C(N)N
• Canonical SMILES: OC(=O)C[C@@H]1NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N(C(=O)[C@H](NC1=O)Cc1ccccc1)C)C(C)C
• InChI: InChI=1S/C27H40N8O7/c1-15(2)22-25(41)33-17(10-7-11-30-27(28)29)23(39)31-14-20(36)32-18(13-21(37)38)24(40)34-19(26(42)35(22)3)12-16-8-5-4-6-9-16/h4-6,8-9,15,17-19,22H,7,10-14H2,1-3H3,(H,31,39)(H,32,36)(H,33,41)(H,34,40)(H,37,38)(H4,28,29,30)/t17-,18-,19+,22-/m0/s1
• InChIKey: AMLYAMJWYAIXIA-VWNVYAMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,5R,8S,11S)-5-benzyl-11-{3-[(diaminomethylidene)amino]propyl}-7-methyl-3,6,9,12,15-pentaoxo-8-(propan-2-yl)-1,4,7,10,13-pentaazacyclopentadecan-2-yl]acetic acid
• IUPAC Traditional name: cilengitide
• Synonyms: Cilengitide

Database IDs

• CAS Number: 188968-51-6
• PubChem SID: 162220925
• PubChem CID: 176873
• CHEMBL: 429876
• Chemspider ID: 154046
• KEGG ID: D03497
• MeSH Name: Cilengitide
• Wikipedia Title: Cilengitide

CALCULATED PROPERTIES

• Acid pKa: 3.675578
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -3.7401316
• LogD (pH = 7.4): -3.735223
• Log P: -3.7350945
• Molar Refractivity: 149.6728 cm^3
• Polarizability: 58.017895 Å^3
• Polar Surface Area: 238.41 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Density: 1.417 g/mL