Structure Database (LMSD)

Common Name
Amentoflavone
Systematic Name
(4',5,7-Trihydroxyflavone)-(3'-8)-(4',5,7-trihydroxyflavone)
Synonyms
  • 3',8''-biapigenin
LM ID
LMPK12040009
Formula
Exact Mass
Calculate m/z
538.09
Status
Curated




Classification

Biological Context

Amentoflavone is a biflavonoid originally isolated from Selaginella. It has a wide variety of biological effects including antibacterial, antioxidant, antiviral, antidiabetic, and neuroprotective activities.1,2,3,4 Amentoflavone has antiviral activity against the influenza A subtypes H1N1 and H3N2, influenza B, and herpes simplex virus 1 (EC50s = 3.1 and 4.3, 0.56, and 17.9 µg/ml, respectively).5 It has antidiabetic effects such that it dose-dependently increases insulin receptor phosphorylation and activation and inhibits hydrolysis of p-nitrophenyl phosphate (p-NPP) catalyzed by protein tyrosine phosphatase 1B (PTP1B; IC50 = 7.3 µM).6 Amentoflavone reduces the time mice spend immobile in the forced swim test, a measure of antidepressant efficacy, in a dose-dependent manner.7

This information has been provided by Cayman Chemical

References

4. Lee, S., Kim, H., Kang, J.-W., et al. The biflavonoid amentoflavone induces apoptosis via suppressing E7 expression, cell cycle arrest at sub-G₁ phase, and mitochondria-emanated intrinsic pathways in human cervical cancer cells. J. Med. Chem. 14(7), 808-816 (2011).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ginkgo biloba (#3311)
Ginkgoopsida (#29811)
Flavonoids of Ginkgo biloba,
Ginkgo Biloba A Global Treasure, 1997

String Representations

InChiKey (Click to copy)
YUSWMAULDXZHPY-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC(O)=C(C4=C(O)C=C(O)C5C(=O)C=C(C6=CC=C(O)C=C6)OC4=5)C=3)=CC(=O)C=2C(O)=C1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 6
Aromatic Rings 6
Rotatable Bonds 3
Van der Waals Molecular Volume 433.66
Topological Polar Surface Area 181.80
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 10
logP 6.93
Molar Refractivity 145.04

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Created at
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Updated at
12th Jun 2024