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
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
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 Target | Pharmacology | Condition | Potency |
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Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25321472 |
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Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21333515 |
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Target ID: P20029 Gene ID: 14828.0 Gene Symbol: Hspa5 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27316719 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines. | 2000 Jul-Aug |
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Profiling isoflavonoids found in legume root extracts using capillary electrophoresis. | 2002 Jun |
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Identification of cDNAs encoding pterocarpan reductase involved in isoflavan phytoalexin biosynthesis in Lotus japonicus by EST mining. | 2006 Oct 16 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21333515
Rat: 5 mg/kg single dose
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25321472
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.
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SUBSTANCE RECORD