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Bigelovin

Bigelovin structure

Bigelovin 

structure
  • CAS No:

    3668-14-2

  • Formula:

    C17H20O5

  • Chemical Name:

    Bigelovin

  • Synonyms:

    Azuleno[6,5-b]furan-2,5-dione,4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-,(3aR,4S,4aR,7aR,8R,9aS)-;Ambrosa-2,11(13)-dien-12-oic acid,6α,8α-dihydroxy-4-oxo-,12,8-lactone,acetate;Bigelovin;Azuleno[6,5-b]furan-2,5-dione,4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-,[3aR-(3aα,4α,4aβ,7aα,8α,9aβ)]-;(3aR,4S,4aR,7aR,8R,9aS)-4-(Acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione;Bigelovine;48191-72-6

  • Categories:

    Natural Products  >  Flavonoids

Description

ChEBI: A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupe ensis, it exhibits antineoplastic activity.


Bigelovin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity. It has a role as an apoptosis inducer, an immunomodulator, an antineoplastic agent and a plant metabolite. It is an acetate ester, an organic heterotricyclic compound, a sesquiterpene lactone, a cyclic ketone and a gamma-lactone.

Bigelovin Basic Attributes

304.3377

304.34

DTXSID80190130

Characteristics

69.7

2

180-182 °C @ Solvent: Acetone, Dichloromethane

Drug Information

bigelovin

Computed Properties

Molecular Weight:304.34
XLogP3:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:304.13107373
Monoisotopic Mass:304.13107373
Topological Polar Surface Area:69.7
Heavy Atom Count:22
Complexity:604
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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