cinnamtannin B1   Click here for help

GtoPdb Ligand ID: 13186

Synonyms: Cinnamtannin B-1 | CTB-1
PDB Ligand
Compound class: Natural product or derivative
Comment: Cinnamtannin B1 is naturally produced by Cinnamomum (cinnamon) species trees [1]. Chemically it is a proanthocyanidin compound. Anti-tumour, antioxidant and wound healing activities have been reported [2-3,5-7].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 18
Hydrogen bond donors 14
Rotatable bonds 4
Topological polar surface area 320.14
Molecular weight 864.76
XLogP 1.07
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C1=C(C=C(C(=C1)O)O)[C@@H]2[C@@H](CC3=C(C=C(C(=C3O2)[C@H]4C5=C(C=C6C(=C5O[C@H](C7=CC=C(C(=C7)O)O)[C@@H]4O)[C@H]8C9=C(C=C(C=C9O)O)O[C@](C%10=CC=C(C(=C%10)O)O)([C@@H]8O)O6)O)O)O)O
Isomeric SMILES C1[C@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=C3C(=CC5=C4[C@@H]6[C@H]([C@](O5)(OC7=CC(=CC(=C67)O)O)C8=CC(=C(C=C8)O)O)O)O)C9=CC(=C(C=C9)O)O)O)O)O)C%10=CC(=C(C=C%10)O)O)O
InChI 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
InChI Key BYSRPHRKESMCPO-LQNPQWRQSA-N
References
1. Anderson RA, Broadhurst CL, Polansky MM, Schmidt WF, Khan A, Flanagan VP, Schoene NW, Graves DJ. (2004)
Isolation and characterization of polyphenol type-A polymers from cinnamon with insulin-like biological activity.
J Agric Food Chem, 52 (1): 65-70. [PMID:14709014]
2. Carriere PP, Kapur N, Mir H, Ward AB, Singh S. (2018)
Cinnamtannin B-1 inhibits cell survival molecules and induces apoptosis in colon cancer.
Int J Oncol, 53 (4): 1442-1454. [PMID:30066888]
3. Chi Z, Ma X, Cui G, Li M, Li F. (2013)
Cinnamtannin B-1 regulates cell proliferation of spinal cord astrocytes and protects the cell from oxygen-glucose-serum deprivation/reoxygenation-induced apoptosis.
Int J Mol Sci, 14 (8): 15827-37. [PMID:23903044]
4. FDA. 
Cinnamtannin B-1.
Accessed on 26/02/2024. Modified on 26/02/2024. fda.gov, https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=986523
5. Fujita K, Kuge K, Ozawa N, Sahara S, Zaiki K, Nakaoji K, Hamada K, Takenaka Y, Tanahashi T, Tamai K et al.. (2015)
Cinnamtannin B-1 Promotes Migration of Mesenchymal Stem Cells and Accelerates Wound Healing in Mice.
PLoS One, 10 (12): e0144166. [PMID:26657737]
6. Jia J, Xia J, Liu W, Tao F, Xiao J. (2023)
Cinnamtannin B-1 Inhibits the Progression of Osteosarcoma by Regulating the miR-1281/PPIF Axis.
Biol Pharm Bull, 46 (1): 67-73. [PMID:36273900]
7. López JJ, Jardín I, Salido GM, Rosado JA. (2008)
Cinnamtannin B-1 as an antioxidant and platelet aggregation inhibitor.
Life Sci, 82 (19-20): 977-82. [PMID:18433795]
8. Li M, Hao L, Li L, Liu L, Chen G, Jiang W, Xu W, Zhu C, Yao G, Fang S. (2020)
Cinnamtannin B-1 Prevents Ovariectomy-Induced Osteoporosis via Attenuating Osteoclastogenesis and ROS Generation.
Front Pharmacol, 11: 1023. [PMID:32754032]