Structure Database (LMSD)

Common Name
Neobavaisoflavone
Systematic Name
Synonyms
LM ID
LMPK12050027
Formula
C20H18O4
Exact Mass
Calculate m/z
322.12051
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Isoflavonoids [PK1205]

Biological Context

Neobavaisoflavone is a natural isoflavone that was first isolated from seeds of P. corylifolia, which are used in traditional herbal medicine to treat various skin diseases. Neobavaisoflavone has been found to have diverse effects in isolated mammalian cells, including inhibiting DNA polymerase and carboxylesterase 1 (Ki = 5.3 µM).1,2 It also displays antibiotic activity against Gram-negative multidrug resistant bacteria.3

This information has been provided by Cayman Chemical

References

1. Sun, N.J., Woo, S.H., Cassady, J.M., et al. DNA polymerase and topoisomerase II inhibitors from Psoralea corylifolia. J. Nat. Prod. 61(3), 362-366 (1998).
2. Mbaveng, A.T., Sandjo, L.P., Tankeo, S.B., et al. Antibacterial activity of nineteen selected natural products against multi-drug resistant Gram-negative phenotypes. SpringerPlus 4:823, (2015).
3. Sun, D.X., Ge, G.B., Dong, P.P., et al. Inhibition behavior of fructus psoraleae’s ingredients towards human carboxylesterase 1 (hCES1). Xenobiotica 46(6), 503-510 (2016).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
OBGPEBYHGIUFBN-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H18O4/c1-12(2)3-4-14-9-13(5-8-18(14)22)17-11-24-19-10-15(21)6-7-16(19)20(17)23/h3,5-11,21-22H,4H2,1-2H3
SMILES (Click to copy)
C1(O)=CC2OC=C(C3C=CC(O)=C(C/C=C(/C)\C)C=3)C(=O)C=2C=C1

Other Databases

CHEBI ID
66614
METABOLOMICS ID
FLIA1ANI0001
PubChem CID
5320053
Cayman ID
19852

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 3
Aromatic Rings 3
Rotatable Bonds 3
Van der Waals Molecular Volume 296.18
Topological Polar Surface Area 70.67
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 5.28
Molar Refractivity 94.49

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