Compounds > medicarpin, (6as-cis)-isomer
Page last updated: 2024-12-06

medicarpin, (6as-cis)-isomer

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

(+)-medicarpin : The (+)-enantiomer of medicarpin. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID73067
CHEMBL ID413297
CHEBI ID6714
SCHEMBL ID19999732
MeSH IDM0322591

Synonyms (22)

Synonym
CHEBI:6714 ,
(6as,11as)-9-methoxy-6a,11a-dihydro-6h-[1]benzofuro[3,2-c]chromen-3-ol
(+)-medicarpin
33983-39-0
C01729
CHEMBL413297
(6as,11as)-medicarpan
(6as,11as)-medicarpin
(6as,11as)-demethylhomopterocarpin
(+)-medicrpin
(6as, 11as)-medicarpin
SCHEMBL19999732
Q27107309
CS-0032253
HY-N6052
(6as,11as)-9-methoxy-6a,11a-dihydro-6h-benzofuro[3,2-c]chromen-3-ol
(+/-)-medicarpin
DTXSID80872005
(1s,10s)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0?,?.0??,??]heptadeca-2(7),3,5,11,13,15-hexaen-5-ol
AKOS040740841
(+)-(6as,11as)-medicarpin
9-methoxy-6a,11a-dimethyl-6a,11a-dihydro-6h-\\ 1-benzofuro[3,2-c]chromen-3-ol from dalbergia oliveri
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
medicarpinA member of the class of pterocarpans that is 3-hydroxyptercarpan with a methoxy substituent at position 9.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID379755Antimicrobial activity against Pseudomonas aeruginosa PA14 by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID404184Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID379754Antimicrobial activity against wild-type Escherichia coli K12 by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID379763Inhibition of NorA efflux pump in Staphylococcus aureus K1758 mutant assessed as fold reduction of berberine MIC at 56 uM by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID1328377Anthelmintic activity against Ancylostoma ceylanicum isolated from infected Syrian hamster feces assessed as survival rate at 25 ug/ml measured on day 4 relative to control2016Journal of natural products, 09-23, Volume: 79, Issue:9
Phenolic Metabolites of Dalea ornata Affect Both Survival and Motility of the Human Pathogenic Hookworm Ancylostoma ceylanicum.
AID379753Antimicrobial activity against wild-type Staphylococcus aureus 8325-4 by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID379761Inhibition of NorA efflux pump in wild-type Staphylococcus aureus 8325-4 assessed as fold reduction of berberine MIC at 56 uM by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID1328375Anthelmintic activity against Ancylostoma ceylanicum isolated from infected Syrian hamster feces assessed as survival rate at 25 ug/ml measured on day 2 relative to control2016Journal of natural products, 09-23, Volume: 79, Issue:9
Phenolic Metabolites of Dalea ornata Affect Both Survival and Motility of the Human Pathogenic Hookworm Ancylostoma ceylanicum.
AID379752Inhibition of NorA efflux pump in Staphylococcus aureus K2361 mutant overexpressing NorA assessed as potentiation of berberine-induced antimicrobial activity at 56 uM by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID1328379Effect on Syrian hamster splenocytes proliferation assessed as stimulation index by BrdU-incorporation based colorimetric analysis2016Journal of natural products, 09-23, Volume: 79, Issue:9
Phenolic Metabolites of Dalea ornata Affect Both Survival and Motility of the Human Pathogenic Hookworm Ancylostoma ceylanicum.
AID404182Cytotoxicity against human A549 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID313354Cytotoxicity against human PANC1 cells in nutrient deprived medium after 24 hrs2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.
AID358614Cytotoxicity against human KB cells2001Journal of natural products, Nov, Volume: 64, Issue:11
Macharistol, a new cytotoxic cinnamylphenol from the stems of Machaerium aristulatum.
AID379756Antimicrobial activity against Saccharomyces cerevisiae BY4742 by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID404183Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID404180Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID379766Antimicrobial activity against Enterococcus faecalis V583 by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID404179Cytotoxicity against mouse colon 26-L5 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID404181Cytotoxicity against mouse LLC cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID1328376Anthelmintic activity against Ancylostoma ceylanicum isolated from infected Syrian hamster feces assessed as survival rate at 25 ug/ml measured on day 3 relative to control2016Journal of natural products, 09-23, Volume: 79, Issue:9
Phenolic Metabolites of Dalea ornata Affect Both Survival and Motility of the Human Pathogenic Hookworm Ancylostoma ceylanicum.
AID1328378Anthelmintic activity against Ancylostoma ceylanicum isolated from infected Syrian hamster feces assessed as survival rate at 25 ug/ml measured on day 5 (Rvb = >95%)2016Journal of natural products, 09-23, Volume: 79, Issue:9
Phenolic Metabolites of Dalea ornata Affect Both Survival and Motility of the Human Pathogenic Hookworm Ancylostoma ceylanicum.
AID379757Antimicrobial activity against Candida albicans F5 by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID379758Inhibition of MDR protein in wild-type Staphylococcus aureus 8325-4 assessed as potentiation of antimicrobial activity of berberine after 18 hrs by twofold serial dilution method2006Journal of natural products, Feb, Volume: 69, Issue:2
Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus.
AID1328374Anthelmintic activity against Ancylostoma ceylanicum isolated from infected Syrian hamster feces assessed as survival rate at 25 ug/ml measured on day 1 relative to control2016Journal of natural products, 09-23, Volume: 79, Issue:9
Phenolic Metabolites of Dalea ornata Affect Both Survival and Motility of the Human Pathogenic Hookworm Ancylostoma ceylanicum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (80.00)29.6817
2010's1 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.50

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.50 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.4420nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
rotenone
Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.		2.1310organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
mitochondrial NADH:ubiquinone reductase inhibitor;
phytogenic insecticide;
piscicide;
toxin
Berberine chloride (TN)
[no description available]		2.0310organic molecular entity
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.0410taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
arctigenin
arctigenin: precursor to catechols; in many plants		2.0410lignan
(+)-Eudesmin
[no description available]		2.4420lignan
deguelin
deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.		2.1310aromatic ether;
diether;
organic heteropentacyclic compound;
rotenones		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
apoptosis inducer;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
mitochondrial NADH:ubiquinone reductase inhibitor;
plant metabolite
liquiritigenin
liquiritigenin: structure given in first source; isolated from Pterocarpus marsupium. 4',7-dihydroxyflavanone : A dihydroxyflavanone in which the two hydroxy substituents are located at positions 4' and 7.. liquiritigenin : A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta.		2.44204',7-dihydroxyflavanonehormone agonist;
plant metabolite
tephrosin
tephrosin: RN given for (7aR-cis)-isomer; has insecticidal activity; structure in first source. tephrosin : A member of the class of rotenones that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted with geminal methyl groups at position 3, hydroxy group at position 7a and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). It is isolated from the leaves and twigs of Antheroporum pierrei and exhibits antineoplastic and pesticidal activities.		2.1310aromatic ether;
cyclic ketone;
organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
pesticide
inermin
(+)-maackiain : The (+)-enantiomer of maackiain.		2.4520maackiain
naringenin
(S)-naringenin : The (S)-enantiomer of naringenin.		2.4420(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite
mucronulatol
mucronulatol: compound from Caribbean propolis that exerts cytotoxic effects on human tumor cell lines. mucronulatol : A methoxyisoflavan that is (S)-isoflavan substituted by methoxy groups at positions 2' and 4' and hydroxy groups at positions 7 and 3' respectively.		2.4420hydroxyisoflavans;
methoxyisoflavan		antineoplastic agent;
plant metabolite
syringaresinol
(+)-syringaresinol : The (7alpha,7'alpha,8alpha,8'alpha)-stereoisomer of syringaresinol.		2.4420syringaresinolantineoplastic agent
isoliquiritigenin
[no description available]		2.4420chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
(2S)-7-hydroxyflavanone
[no description available]		2.44207-hydroxyflavanone
leachianone g
leachianone G: structure in first source. leachianone G : A tetrahydroxyflavanone having the hydroxy groups at the 2'-, 4'-, 5- and 7-positions and a prenyl group at 8-position.		2.1310(2S)-flavan-4-one;
4'-hydroxyflavanones;
tetrahydroxyflavanone
biochanin a
[no description available]		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones		antineoplastic agent;
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
formononetin
[no description available]		2.72304'-methoxyisoflavones;
7-hydroxyisoflavones		phytoestrogen;
plant metabolite
7,3'-dihydroxy-4'-methoxyisoflavone
7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones		antioxidant;
metabolite
2'-hydroxyformononetin
2'-hydroxyformononetin : A member of the class of 4'-methoxyisoflavones that is formononetin with a hydroxy group at the 2'position.		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones		anti-inflammatory agent
daidzein
[no description available]		2.44207-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
phytoestrogen;
plant metabolite
4'-methoxy-3',5,7-trihydroxyisoflavone
4'-methoxy-3',5,7-trihydroxyisoflavone: structure in first source. pratensein : A member of the class of 7-hydroxyisoflavones in which isoflavone is substituted by hydroxy groups at the 5, 7, and 3' positions, and by a methoxy group at the 4' position.		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones
3-deoxysappanchalcone
3-deoxysappanchalcone: Anti-allergic from the roots and heartwood of Caesalpinia sappan; structure in first source. 2'-O-methylisoliquiritigenin : A member of the class of chalcones that is isoliquiritigenin in which one of the hydroxy groups at position 2' is replaced by a methoxy group.		2.4420chalcones;
monomethoxybenzene;
phenols		metabolite
2',4'-dihydroxychalcone
2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source		2.4420
(-)-pinoresinol
(-)-pinoresinol : An enantiomer of pinoresinol having (-)-1R,3aS,4R,6aS-configuration.		2.4420pinoresinolplant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Nasopharynx
[description not available]		0210
Nasopharyngeal Neoplasms
Tumors or cancer of the NASOPHARYNX.		0210
Cancer of Pancreas
[description not available]		02.0410
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.0410
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.0410
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0410
Benign Neoplasms
[description not available]		02.0410
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0410
Disease Resistance
The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.		02.1310
Ancylostomiasis
Infection of humans or animals with hookworms of the genus ANCYLOSTOMA. Characteristics include anemia, dyspepsia, eosinophilia, and abdominal swelling.		02.1310
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1310