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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P20029
Gene ID: 14828.0
Gene Symbol: Hspa5
Target Organism: Mus musculus (Mouse)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.
2000 Jul-Aug
Profiling isoflavonoids found in legume root extracts using capillary electrophoresis.
2002 Jun
Constituents of the roots of Pueraria lobata inhibit formation of advanced glycation end products (AGEs).
2006 Oct
Identification of cDNAs encoding pterocarpan reductase involved in isoflavan phytoalexin biosynthesis in Lotus japonicus by EST mining.
2006 Oct 16
Patents

Patents

Sample Use Guides

Rat: 5 mg/kg single dose
Route of Administration: Oral
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
Created
by admin
on Fri Dec 15 19:10:38 GMT 2023
Edited
by admin
on Fri Dec 15 19:10:38 GMT 2023
Record UNII
6TX086I6IG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEDICARPIN
MI  
Common Name English
(-)-3-HYDROXY-9-METHOXYPTEROCARPAN
Common Name English
NSC-350085
Code English
MEDICARPIN, (-)-
Common Name English
MEDICARPIN [MI]
Common Name English
DEMETHYLHOMOPTEROCARPIN
Common Name English
(6AR,11AR)-6A,11A-DIHYDRO-9-METHOXY-6H-BENZOFURO(3,2-C)(1)BENZOPYRAN-3-OL
Common Name English
L-3-HYDROXY-9-METHOXYPTEROCARPAN
Common Name English
Code System Code Type Description
FDA UNII
6TX086I6IG
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
WIKIPEDIA
MEDICARPIN
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
CAS
32383-76-9
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
MESH
C047353
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
CHEBI
16114
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
NSC
350085
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
MERCK INDEX
m7130
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID301026587
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
PUBCHEM
336327
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
CHEBI
6714
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
CHEBI
100
Created by admin on Fri Dec 15 19:10:38 GMT 2023 , Edited by admin on Fri Dec 15 19:10:38 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT