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Details

Stereochemistry ACHIRAL
Molecular Formula C20H16O5
Molecular Weight 336.338
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PSORALIDIN

SMILES

CC(C)=CCC1=C(O)C=C2OC(=O)C3=C(OC4=CC(O)=CC=C34)C2=C1

InChI

InChIKey=YABIJLLNNFURIJ-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Psoralidin (1) was first isolated from seeds of Psoralea corylifolia Linn. It was found to be an active ingredient of many Indian and Chinese traditional herbal medicines. Psoralidin exhibits a variety of biological activities like antineoplastic, antioxidant, antibacterial, antidepressant activities. Psoralidin inhibits protein tyrosine phosphatase 1B activity. Psoralidin may act as a estrogen receptor agonist. In addition psoralidin showed potent and noncompetitive inhibition against UDP- glucuronosyltransferase (UGT) or cytochrome p450 (CYP450) enzymes.

CNS Activity

Curator's Comment: Psoralidin is CNS active in animals. No human data available.

Originator

Sources: Chakravarti KK, Bose AK, Siddiqui S. J Sci Ind Res. 1948;7B:24–26.
Curator's Comment: Psoralidin was first isolated from seeds of Psoralea corylifolia Linn in 1948 by Chakravarti et al. and later its structure was corrected by Khastgir et al. in 1961. reference was retrieved from https://www.ncbi.nlm.nih.gov/pubmed/19254011

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia.
2005 Jan
[Isolation and structure identification of a new isoflavone from Psoralea corylifolias].
2006 Jan
Identification of a potent herbal molecule for the treatment of breast cancer.
2009 Jan 30
Psoralidin, an herbal molecule, inhibits phosphatidylinositol 3-kinase-mediated Akt signaling in androgen-independent prostate cancer cells.
2009 Mar

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In vivo, psoralidin effectively suppressed CTPE xenografts growth, without any observable toxicity.
Unknown
Route of Administration: Oral
A cytotoxic coumestan derivative, psoralidin was isolated from the seed of Psoralea corylifolia. The IC50 values of 1 against SNU-1 and SNU-16 carcinoma cell lines were 53 and 203 micrograms/ml, respectively, indicating cytotoxic activity against stomach carcinoma cell lines. Psoralidin was found to be a cytotoxic with the IC50 values of 0.3 and 0.4 microg/ml against the HT-29 (colon) and MCF-7 (breast) human cancer cell lines, respectively.
Name Type Language
PSORALIDIN
MI  
Common Name English
6H-BENZOFURO(3,2-C)(1)BENZOPYRAN-6-ONE, 3,9-DIHYDROXY-2-(3-METHYL-2-BUTENYL)-
Systematic Name English
PSORALIDIN [MI]
Common Name English
3-BENZOFURANCARBOXYLIC ACID, 2-(2,4-DIHYDROXY-5-(3-METHYL-2-BUTENYL)PHENYL)-6-HYDROXY-, .DELTA.-LACTONE
Systematic Name English
Code System Code Type Description
FDA UNII
G16ZUQ069L
Created by admin on Sat Dec 16 09:32:21 GMT 2023 , Edited by admin on Sat Dec 16 09:32:21 GMT 2023
PRIMARY
PUBCHEM
5281806
Created by admin on Sat Dec 16 09:32:21 GMT 2023 , Edited by admin on Sat Dec 16 09:32:21 GMT 2023
PRIMARY
CAS
18642-23-4
Created by admin on Sat Dec 16 09:32:21 GMT 2023 , Edited by admin on Sat Dec 16 09:32:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID20171903
Created by admin on Sat Dec 16 09:32:21 GMT 2023 , Edited by admin on Sat Dec 16 09:32:21 GMT 2023
PRIMARY
MERCK INDEX
m442
Created by admin on Sat Dec 16 09:32:21 GMT 2023 , Edited by admin on Sat Dec 16 09:32:21 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
Psoralidin
Created by admin on Sat Dec 16 09:32:21 GMT 2023 , Edited by admin on Sat Dec 16 09:32:21 GMT 2023
PRIMARY