Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C45H36O18 |
| Molecular Weight | 864.7565 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1CC2=C(O[C@@H]1C3=CC=C(O)C(O)=C3)C([C@@H]4[C@@H](O)[C@H](OC5=C6[C@@H]7[C@@H](O)[C@@](OC8=CC(O)=CC(O)=C78)(OC6=CC(O)=C45)C9=CC=C(O)C(O)=C9)C%10=CC=C(O)C(O)=C%10)=C(O)C=C2O
InChI
InChIKey=BYSRPHRKESMCPO-WIYGYKBVSA-N
InChI=1S/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/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38?,39-,40-,41-,44-,45+/m1/s1
| Molecular Formula | C45H36O18 |
| Molecular Weight | 864.7565 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Cinnamtannin B-1 is a naturally occurring A-type proanthocyanidins, available in a limited number of plants, including C. zeylanicum and L. nobilis, that exhibit a large number of cellular actions mostly derived from its antioxidant activity, including antitumoral activity mediated by a selective pro-apoptotic action in a number of tumoral cell lines associated with a remarkable antiapoptotic activity in normal cells. In addition, cinnamtannin B-1 shows antithrombotic actions through inhibition of platelets' endogenous ROS generation,
Ca2 mobilization and subsequently aggregation. This has been reported to be especially relevant in platelets from diabetic patients where cinnamtannin B-1 reverses both platelet hypersensitivity and
hyperactivity. Considering the large number of cellular effects of cinnamtannin B-1, this compound might be further investigated for the development of therapeutic strategies based on its use for thrombotic disorders or certain types of cancer. Cinnamtannin B-1 is a potent antioxidant and protective agent against oxidative stress and apoptosis in human platelets. Cinnamtannin B-1 is a Cox-2 (cyclooxygenase-2) inhibitor. Cinnamtannin B1 was a potent cancer cell proliferation inhibitor and a good intracellular antioxidant.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25857215 |
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Target ID: GO:0016209 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10528992 |
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Target ID: GO:0070527 |
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Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21875098 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structural characterization and bioactivity of proanthocyanidins from indigenous cinnamon (Cinnamomum osmophloeum). | 2016-11 |
|
| Trimer procyanidin oligomers contribute to the protective effects of cinnamon extracts on pancreatic β-cells in vitro. | 2016-08 |
|
| Identification of phenolics in litchi and evaluation of anticancer cell proliferation activity and intracellular antioxidant activity. | 2015-07 |
|
| Immunosuppressive Effects of A-Type Procyanidin Oligomers from Cinnamomum tamala. | 2014 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26657737
Mice: Six male C57BL/6 mice each from the control and cinnamtannin B-1-treated groups were injected with 0.4 mL phosphate-buffered saline (PBS) or cinnamtannin B-1 solution (2.0 mg/kg via the vena caudalis), respectively.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20002836
Cinnamtannin B-1 (10 uM) significantly reduced Ca(2+) influx in mouse pancreatic acinar cells evoked by cholecystokinin in the presence of ethanol.
| Substance Class |
Chemical
Created
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admin
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Edited
Tue Apr 01 16:23:36 GMT 2025
by
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Tue Apr 01 16:23:36 GMT 2025
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H1059K9GIN
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Validated (UNII)
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Cinnamtannin B1
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PARENT -> CONSTITUENT ALWAYS PRESENT |