8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate

• ChemBase ID: 105151
• Molecular Formular: C30H42N2O9
• Molecular Mass: 574.66248
• Monoisotopic Mass: 574.28903093
• SMILES: COC1CC(C)C(OC)C2=CC(=O)C=C(NC(=O)/C(=C\C=C\C(OC)C(OC(=O)N)/C(=C/C(C)C1OC)/C)/C)C2=O
• Canonical SMILES: COC1C(C)/C=C(\C)/C(OC(=O)N)C(OC)/C=C/C=C(\C(=O)NC2=CC(=O)C=C(C(C(CC1OC)C)OC)C2=O)/C
• InChI: InChI=1S/C30H42N2O9/c1-16-10-9-11-23(37-5)28(41-30(31)36)18(3)12-17(2)27(40-8)24(38-6)13-19(4)26(39-7)21-14-20(33)15-22(25(21)34)32-29(16)35/h9-12,14-15,17,19,23-24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)
• InChIKey: MCAHMSDENAOJFZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
• IUPAC Traditional name: 8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
• Synonyms: HERBIMYCIN A

Database IDs

• CAS Number: 70563-58-5
• PubChem SID: 162092063
• PubChem CID: 5477282

CALCULATED PROPERTIES

• Acid pKa: 12.811985
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 2.6904206
• LogD (pH = 7.4): 2.6904192
• Log P: 2.6904206
• Molar Refractivity: 156.9016 cm^3
• Polarizability: 59.414272 Å^3
• Polar Surface Area: 152.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C, Protect from light
• RTECS: LX8930000

DETAILS

MP Biomedicals - 02158928

From Streptomyces hygroscopicus
Irreversibly inhibits tyrosine kinsases. Also, inhibits thrombin-stimulated tyrosine phosphorylation of phospholipase C. Antibiotic against Src, Yes, Fps, Ros, and, Erb oncongene reagents.

REFERENCES

• Satoh, T., et al., J. Biol. Chem. , 267 : 2537, (1992).
• Weiss, R. and Nuccitelli, R., J. Biol. Chem. , 267 : 5608, (1992).
• Uehara, Y. and Fukazawa, H., Methods Enzymol. , 201 : 370, (1991).
• Fukazawa, H., et al., Biochem. Pharmacol. , 42 : 1661, (1991).