(1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one

• ChemBase ID: 4999
• Molecular Formular: C16H24O4
• Molecular Mass: 280.35936
• Monoisotopic Mass: 280.16745925
• SMILES: O[C@H]1C[C@@H]2[C@@H](C1)[C@@H](/C=C/C(=O)O[C@H](CCC/C=C/2)C)O
• Canonical SMILES: O[C@@H]1C[C@@H]2[C@@H](C1)/C=C/CCC[C@@H](OC(=O)/C=C/[C@H]2O)C
• InChI: InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
• InChIKey: KQNZDYYTLMIZCT-KQPMLPITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one
• IUPAC Traditional name: brefeldin A
• Synonyms: BFA; 1,6,7,8,9,11A,12,13,14,14A-DECAHYDRO-1,13-DIHYDROXY-6-METHYL-4H-CYCLOPENT[F]OXACYCLOTRIDECIN-4-ONE; γ-4-Dihdyroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic Acid, λ-Lactone, BFA, Cyanein, Ascotoxin, Decumbin; NSC 244390; NSC 56310; NSC 89671; Nectrolide; Synergisidin; Brefeldin A

Database IDs

• CAS Number: 20350-15-6
• PubChem SID: 99443819; 160968431
• PubChem CID: 5287620

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.419293
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.007216
• LogD (pH = 7.4): 2.007216
• Log P: 2.007216
• Molar Refractivity: 78.7488 cm^3
• Polarizability: 30.270922 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.73
• LOG S: -2.54
• Solubility (Water): 8.12e-01 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 206-208°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: ATPase

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB07348

Drug information: experimental

Toronto Research Chemicals - B677240

A macrolide isolated from Penicillium brefeldianum. It affects the vesticular transport of the Golgi apparatus and induces DNA fragmentation which leads to apoptosis.

REFERENCES

• Misumi, Y., et al.: J. Biol. Chem., 261 (1986)
• Mordente, J.A., et al.: J. Urol., 159, 275 (1986)
• Erokhina, M.V., et al.: Membr. Cell Biol., 12, 871 (1986)
• Nojiri, H., et al.: FEBS Letters, 453, 140 (1986)