Page last updated: 2024-12-07

yakuchinone-a

Description

yakuchinone-A: from Alpinia oxyphylla; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone : A ketone that is heptan-3-one substituted by a 4-hydroxy-3-methoxyphenyl group at position 1 and a phenyl group at position 7. Isolated from in Alpinia oxyphylla, it exhibits antineoplastic and inhibitory activities against COX-1, COX-2 and NO synthase. [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]

FloraRankFlora DefinitionFamilyFamily Definition
AlpiniagenusA plant genus of the family ZINGIBERACEAE. Members contain galangin, yakuchinone-A, and diarylheptanoids.[MeSH]ZingiberaceaeA plant family of the order Zingiberales, subclass Zingiberidae, class Liliopsida. It includes plants which have both flavoring and medicinal properties such as GINGER; turmeric (CURCUMA), and cardamom (ELETTARIA).[MeSH]
Alpinia oxyphyllaspecies[no description available]ZingiberaceaeA plant family of the order Zingiberales, subclass Zingiberidae, class Liliopsida. It includes plants which have both flavoring and medicinal properties such as GINGER; turmeric (CURCUMA), and cardamom (ELETTARIA).[MeSH]

Cross-References

ID SourceID
PubMed CID133145
CHEMBL ID4545194
CHEBI ID66033
SCHEMBL ID3677507
MeSH IDM0125630

Synonyms (22)

Synonym
2x58y9jc7l ,
unii-2x58y9jc7l
1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone
yakuchinone-a
78954-23-1
3-heptanone, 1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-
1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptan-3-one
yakuchinone a
C20211
CHEBI:66033
SCHEMBL3677507
DTXSID50229406
AKOS028111033
1-(4-hydroxy-3-methoxy-phenyl)-7-phenyl-heptan-3-one
1-[4-hydroxy-3-methoxyphenyl]-7-phenyl-3-heptanone
Q27134537
1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-3-heptanone
yakuchinone-ayakuchinone-a
CHEMBL4545194
EX-A6680
CS-0082599
HY-123386

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" However, the poor stability, solubility, in vivo bioavailability and weak activity of CU greatly limit its clinical application."( Recent advances of analogues of curcumin for treatment of cancer.
Pi, C; Wei, Y; Ye, Y; Zhao, L; Zhao, S, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
cyclooxygenase 1 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
EC 1.14.13.39 (nitric oxide synthase) inhibitorAn EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role 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]

Drug Classes (3)

ClassDescription
monomethoxybenzeneCompounds containing a benzene skeleton substituted with one methoxy group.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
ketoneA compound in which a carbonyl group is bonded to two carbon atoms: R2C=O (neither R may be H).
[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 (5)

Assay IDTitleYearJournalArticle
AID1511078Cytotoxicity against human B16 cells after 72 hrs by MTT assay2019European journal of medicinal chemistry, Oct-15, Volume: 180Recent advances of analogues of curcumin for treatment of cancer.
AID1511074Cytotoxicity against human A431 cells after 72 hrs by MTT assay2019European journal of medicinal chemistry, Oct-15, Volume: 180Recent advances of analogues of curcumin for treatment of cancer.
AID1511076Cytotoxicity against human SCC25 cells after 72 hrs by MTT assay2019European journal of medicinal chemistry, Oct-15, Volume: 180Recent advances of analogues of curcumin for treatment of cancer.
AID1511075Cytotoxicity against human BCC cells after 72 hrs by MTT assay2019European journal of medicinal chemistry, Oct-15, Volume: 180Recent advances of analogues of curcumin for treatment of cancer.
AID1511077Cytotoxicity against human A375 cells after 72 hrs by MTT assay2019European journal of medicinal chemistry, Oct-15, Volume: 180Recent advances of analogues of curcumin for treatment of cancer.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (21.43)18.7374
1990's2 (14.29)18.2507
2000's4 (28.57)29.6817
2010's4 (28.57)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.15

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.15 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.67 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
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