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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H14O4
Molecular Weight 270.28
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEDICARPIN

SMILES

[H][C@@]12COC3=C(C=CC(O)=C3)[C@]1([H])OC4=CC(OC)=CC=C24

InChI

InChIKey=NSRJSISNDPOJOP-BBRMVZONSA-N
InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3/t13-,16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H14O4
Molecular Weight 270.28
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Medicarpin, is a pterocarpan-type phytoalexin which is also classified as methoxylated isoflavonoid and is one of the major constituents of dietary legumes. Medicarpin is present in chickpea (Cicer arietinum), peanut (Arachis hypogaea), alfalfa (Medicago sativa), red clover (Trifolium pratense) and in an Indian medicinal plant Butea monosperma. Medicarpin, a legume phytoalexin has excellent oral bioavailability and potent antiproliferative activity against breast cancer and acute myeloid leukemia (AML) cells. Medicarpin also inhibits the oncogenic NF-kB signaling by attenuating the TNF-α-induced nuclear translocation of p65. Medicarpin stimulates osteoblast differentiation likely via estrogen receptor (ER) beta, promotes achievement of peak bone mass. Medicarpin inhibits ER stress-induced apoptosis and promotes osteoblast cell survival by targeting GRP78. Medicarpin was isolated as nematicidal constituent from the extract Taverniera abyssinica A.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Curative
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Rat: 5 mg/kg single dose
Route of Administration: Oral
In Vitro Use Guide
Myeloid leukemia cells were incubated in culture media supplemented with dimethyl sulfoxide (DMSO) or various concentrations of Medicarpin (5, 10, 20, 50, 100 uM) or TRAIL (1, 2.5, 5, 10, 25 ng) for 48 h. Medicarpin alone significantly reduced Myeloid leukemia cell viability at higher doses and showed sensitization with various doses of TRAIL in all the cell lines at a dose of 20 uM.
Substance Class Chemical
Record UNII
6TX086I6IG
Record Status Validated (UNII)
Record Version