Structure Database (LMSD)

Common Name
Psoralidin
Systematic Name
3,9-Dihydroxy-2-prenylcoumestan
Synonyms
LM ID
LMPK12090007
Formula
C20H16O5
Exact Mass
Calculate m/z
336.099775
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]
Coumestan flavonoids [PK1209]

Biological Context

Psoralidin is a furanocoumarin isolated from the seeds of P. corylifolia, a medicinal plant found in southeastern Asia, that has been shown to induce cytotoxicity against various cancer cells.1 Through TNF-related apoptosis-inducing ligand-mediated events, psoralidin at 50 μM can induce the death of HeLa cancer cells.2 It also can induce apoptosis of androgen-dependent (LNCaP, C4-2B) and androgen-independent (DU-145, PC-3) prostate cancer cells and inhibit the growth of PC-3 xenograft tumors in nude mice.3

This information has been provided by Cayman Chemical

References

1. Kumar, R., Srinivasan, S., Pahari, P., et al. Activating SAPK-mediated cell death and inhibiting EGFR signaling: A promising therapeutic strategy for prostate cancer. Mol. Cancer Ther. 9(9), 2488-2496 (2010).
2. Pahari, P., and Rohr, J. Total synthesis of psoralidin, an anticancer natural product. J. Org. Chem. 74(7), 2750-2754 (2009).
3. Bronikowska, J., Szliszka, E., Jaworska, D., et al. The coumarin psoralidin enhances anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). Molecules 17(6), 6449-6464 (2012).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
YABIJLLNNFURIJ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3
SMILES (Click to copy)
C1(O)=CC2OC(=O)C3C4C=CC(O)=CC=4OC=3C=2C=C1C/C=C(/C)\C

Other Databases

KEGG ID
C10523
HMDB ID
HMDB0034050
CHEBI ID
8616
METABOLOMICS ID
FLIE1ANI0001
PubChem CID
5281806
Cayman ID
15119

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 4
Aromatic Rings 4
Rotatable Bonds 2
Van der Waals Molecular Volume 281.71
Topological Polar Surface Area 83.81
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 5.51
Molar Refractivity 96.33

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Updated at
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