Page last updated: 2024-12-08

cinnamtannin b-1

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

Description

cinnamtannin B-1: COX2 Inhibitor from bay wood and bark of Cinnamomum cassia; structure in second source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cinnamtannin B-1 : A proanthocyanidin found in Cinnamomum cassia and Cinnamomum zeylanicum. [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
CassiagenusA plant genus of the family FABACEAE. Many species of this genus, including the medicinal C. senna and C. angustifolia, have been reclassified into the Senna genus (SENNA PLANT) and some to CHAMAECRISTA.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]
Cinnamomum cassiaspecies[no description available]LauraceaeA family of mainly aromatic evergreen plants in the order Laurales. The laurel family includes 2,200 species in 45 genera and from these are derived medicinal extracts, essential oils, camphor and other products.[MeSH]

Cross-References

ID SourceID
PubMed CID475277
CHEMBL ID540956
CHEBI ID69304
MeSH IDM0507561

Synonyms (30)

Synonym
8,14-methano-2h,14h-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2h-1-benzopyran-8-yl]-3,4-dihydro-, (2r,3r,4s,8s,14r,15r)-
bis(3,4-dihydroxyphenyl)-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl][?]pentol
bysrphrkesmcpo-lqnpqwrqsa-
inchi=1/c45h36o18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46
CHEMBL540956
chebi:69304 ,
C17631
cinnamtannin b1
(2r,3r,4s,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h,8h,14h-8,14-methano-1,7,9-trioxabenzo[6,7]cycloocta[1,2-a]naphthalene-3,5,11,13,15-pentol
cinnamtannin b-1
88082-60-4
epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin
(1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol
UFK ,
UFN ,
epicatechin(2b->7,4b->8)epicatechin(4b->8)epicatechin
Q5121058
cinnamtanninb-1
epicatechin-(4beta->8,2beta->o->7)-epicatechin-(4alpha->8)-epicatechin
MS-31598
(2r,3r,4s,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-4-((2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-3,4-dihydro-2h,14h-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
ldn0022358
cinnamtannin b1 (constituent of cinnamomum verum bark)
HY-130237
(1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-chromen-8-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
DTXSID601030258
CS-0105921
(-)-epicatechin-(4beta->8, 2beta-o->7)-epicatechin-(4beta->8)-epicatechin)
cinnamtannin b1 (constituent of cinnamomum cassia bark)
AKOS040746705
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
cyclooxygenase 2 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (1)

ClassDescription
proanthocyanidinA flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.
[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 (42)

Assay IDTitleYearJournalArticle
AID296588Effect on thrombin-induced human platelet aggregation assessed as lag time in presence of catalase2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296581Effect on rate of thrombin-induced human platelet aggregation at 1.0 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID358168Cytotoxicity against human HCT8 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID617981Inhibition of human recombinant COX2 expressed in Sf9 cells at 10 ug/mL2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Bioactive A-type proanthocyanidins from Cinnamomum cassia.
AID296591Effect on thrombin-induced human platelet aggregation assessed as lag time in presence of colchicine2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID1700206Induction of apparent modulus of elasticity in human molar dentine after 1 hr by bending method
AID377252Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 0.3 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID377253Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 0.15 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID296585Effect on thrombin-induced human platelet aggregation at 1.0 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID1700207Inhibition of Clostridium histolyticum collagenase-induced degradation of human molar dentin assessed as reduction in degradation after 24 hrs
AID358166Cytotoxicity against human KB cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID358167Cytotoxicity against human A549 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID296589Effect on rate of thrombin-induced human platelet aggregation in presence of catalase2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296592Effect on rate of thrombin-induced human platelet aggregation in presence of colchicine2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296579Effect on ADP-induced human platelet aggregation assessed as lag time at 10 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296587Effect on of ADP-induced human platelet aggregation at 10 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296598Effect on thrombin-induced Btk activation at 10 uM after 30 mins2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296576Effect on thrombin-induced human platelet aggregation assessed as lag time at 0.1 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296586Effect on thrombin-induced human platelet aggregation at 10 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID1176782Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by UV-spectrophotometry2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Unusual C,O-Fused Glycosylapigenins from Serjania marginata Leaves.
AID296600Inhibition of thrombin-induced pp60src activation at 10 uM after 30 mins2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296584Effect on thrombin-induced human platelet aggregation at 0.1 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296593Effect on thrombin-induced human platelet aggregation in presence of colchicine2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296599Effect on thrombin-induced Btk activation in presence of catalase2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID358169Cytotoxicity against human TE671 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID377249Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 2.4 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID296594Effect on thrombin-induced microtubular reorganization at 10 uM after 30 mins2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID497106Inhibition of Bacillus stearothermophilus alpha glucosidase-42010Journal of natural products, Aug-27, Volume: 73, Issue:8
Proanthocyanidins from the leaves of Machilus philippinensis.
AID617983Inhibition of human recombinant COX2 expressed in Sf9 cells at 1000 ug/mL2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Bioactive A-type proanthocyanidins from Cinnamomum cassia.
AID296583Effect on rate of ADP-induced human platelet aggregation at 10 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID377250Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 1.2 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID296580Effect on rate of thrombin-induced human platelet aggregation at 0.1 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID377251Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 0.6 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID296601Inhibition of thrombin-induced pp60src activation in presence of catalase2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296590Effect on thrombin-induced human platelet aggregation in presence of catalase2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296577Effect on thrombin-induced human platelet aggregation assessed as lag time at 1.0 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296602Reduction of thrombin-induced phosphotyrosine content in human platelets at 30 uM after 30 mins2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296582Effect on rate of thrombin-induced human platelet aggregation at 10 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296578Effect on thrombin-induced human platelet aggregation assessed as lag time at 10 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID296575Effect on thrombin-induced calcium mobilization in human platelets2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.
AID617982Inhibition of human recombinant COX2 expressed in Sf9 cells at 100 ug/mL2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Bioactive A-type proanthocyanidins from Cinnamomum cassia.
AID358165Cytotoxicity against human PRMI7951 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (4.00)18.2507
2000's6 (24.00)29.6817
2010's13 (52.00)24.3611
2020's5 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.63

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 Index28.63 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index5.04 (4.65)
Search Engine Demand Index30.30 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]