10-({5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid

• ChemBase ID: 106091
• Molecular Formular: C26H34O7
• Molecular Mass: 458.54396
• Monoisotopic Mass: 458.23045343
• SMILES: COC1C(CCC2(CO2)C1C1(C)OC1CC=C(C)C)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O
• Canonical SMILES: COC1C(CCC2(C1C1(C)OC1CC=C(C)C)CO2)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O
• InChI: InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)
• InChIKey: NGGMYCMLYOUNGM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-({5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid; (2E,4E,6E,8E)-10-({5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: 10-({5-methoxy-4-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid; fumagillin
• Synonyms: FUMAGILLIN; Fumagillin from Aspergillus fumigatus

Database IDs

• CAS Number: 23110-15-8
• EC Number: 245-433-8
• MDL Number: MFCD03990453
• PubChem SID: 24894920; 162092889
• PubChem CID: 5353634

CALCULATED PROPERTIES

• LogD (pH = 7.4): 1.5717199
• Log P: 4.048655
• Molar Refractivity: 128.3748 cm^3
• Polarizability: 48.59852 Å^3
• Polar Surface Area: 97.89 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true
• Acid pKa: 4.884221
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.339205

PROPERTIES

Physical Property

• Solubility: ethanol: soluble1 mg/mL
• Apperance: white powder

Safety Information

• Storage Condition: 2-8°C
• RTECS: HE1750000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%; 98%

DETAILS

MP Biomedicals - 02199027

Purity: 98%
From Aspergillus fumigatus

Sigma Aldrich - F6771

Biochem/physiol Actions
Methionine aminopeptidase-2 (MetAP-2) inhibitor; inhibits endothelial cell proliferation and angiogenesis.