Structure Database (LMSD)

Systematic Name
7,3',4'-Trihydroxyflavone
Synonyms
LM ID
LMPK12110042
Formula
C15H10O5
Exact Mass
Calculate m/z
270.052825
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

7,3’,4’-Trihydroxyflavone is a flavonoid that has been found in A. julibrissin bark and has diverse biological activities.1,2,3,4 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) and peroxynitrite radicals in cell-free assays (IC50s = 2.2 and 5.78 µM, respectively), as well as reduces total reactive oxygen species in rat kidney homogenates (IC50 = 3.9 µM).1 7,3’,4’-Trihydroxyflavone inhibits COX-1 (IC50 = 36.7 µM).2 It is active against M. tuberculosis (MIC = 50 µg/ml).3 It decreases mRNA expression of the osteoclastic marker genes encoding the calcitonin receptor, cathepsin K1 V-ATPase V0 subunit d2 (Atp6v0d2), and dendritic cell specific transmembrane protein (Dcstamp) in and inhibits RANKL-induced osteoclastic differentiation of mouse bone marrow-derived macrophages (BMDMs).4

This information has been provided by Cayman Chemical

References

1. Jung, M.J., Chung, H.Y., Kang, S.S., et al. Antioxidant activity from the stem bark of Albizzia julibrissin. Arch. Pharm. Res. 26(6), 458-462 (2003).
2. Selvam, C., Jachak, S.M., and Bhutani, K.K. Cyclooxygenase inhibitory flavonoids from the stem bark of Semecarpus anacardium Linn. Phytother. Res. 18(7), 582-584 (2004).
3. Chokchaisiri, R., Suaisom, C., Sriphota, S., et al. Bioactive flavonoids of the flowers of Butea monosperma. Chem. Pharm. Bull. (Tokyo) 57(4), 428-432 (2009).
4. Kang, J.H., Lee, J., Moon, M., et al. 3'4'7-Trihydroxyflavone inhibits RANKL-induced osteoclast formation via NFATc1. Pharmazie 70(10), 661-667 (2015).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
PVFGJHYLIHMCQD-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-7,16-17,19H
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(O)C(O)=CC=3)=CC(=O)C=2C=C1

Other Databases

HMDB ID
HMDB0133311
CHEBI ID
196247
METABOLOMICS ID
FL3F1CNS0001
PubChem CID
5322065
Cayman ID
29880
PDB ID
15Z

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 3
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 221.11
Topological Polar Surface Area 90.90
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 3.48
Molar Refractivity 73.02

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