2-{2-[2-(2-{2-[2-(2-amino-4-methylpentanamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido}propanamido)-3-hydroxypropanamido]-3-methylbutanamido}propanoic acid

• ChemBase ID: 155629
• Molecular Formular: C32H61N13O9
• Molecular Mass: 771.90844
• Monoisotopic Mass: 771.4715206
• SMILES: CC(C)CC(C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(C)C(=O)NC(CO)C(=O)NC(C(C)C)C(=O)NC(C)C(=O)O)N
• Canonical SMILES: OCC(C(=O)NC(C(=O)NC(C(=O)O)C)C(C)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(CC(C)C)N)CCCNC(=N)N)CCCNC(=N)N)C
• InChI: InChI=1S/C32H61N13O9/c1-15(2)13-19(33)25(48)42-21(10-8-12-39-32(36)37)27(50)43-20(9-7-11-38-31(34)35)26(49)40-17(5)24(47)44-22(14-46)28(51)45-23(16(3)4)29(52)41-18(6)30(53)54/h15-23,46H,7-14,33H2,1-6H3,(H,40,49)(H,41,52)(H,42,48)(H,43,50)(H,44,47)(H,45,51)(H,53,54)(H4,34,35,38)(H4,36,37,39)
• InChIKey: PPBZOEOSJVJLRX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-(2-{2-[2-(2-amino-4-methylpentanamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido}propanamido)-3-hydroxypropanamido]-3-methylbutanamido}propanoic acid
• IUPAC Traditional name: 2-{2-[2-(2-{2-[2-(2-amino-4-methylpentanamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido}propanamido)-3-hydroxypropanamido]-3-methylbutanamido}propanoic acid
• Synonyms: (-)-TAN 2162; Kendomycin from Streptomyces violaceoruber

Database IDs

• CAS Number: 183202-73-5
• MDL Number: MFCD00076711
• PubChem SID: 162249767; 24896208
• PubChem CID: 3604670

CALCULATED PROPERTIES

• Acid pKa: 3.4128976
• H Acceptors: 16
• H Donor: 15
• LogD (pH = 5.5): -11.054921
• LogD (pH = 7.4): -9.3580885
• Log P: -6.71397
• Molar Refractivity: 215.3462 cm^3
• Polarizability: 75.88815 Å^3
• Polar Surface Area: 381.95 Å^2
• Rotatable Bonds: 25
• 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

Product Information

• Empirical Formula (Hill Notation): C29H42O6

DETAILS

Sigma Aldrich - K1513

Biochem/physiol Actions
Potent endothelin receptor antagonist. Antiosteoporotic compound. Shows also remarkable antibacterial and cytotoxic activity. A putative cellular target for cytotoxicity has been identified: inhibition or altered regulation of the proteasome.1