(2R,3S)-2-(3,4-Dihydroxy-phenyl)-chroman-3,5,7-triol

ID: ALA200715

Chembl Id: CHEMBL200715

Cas Number: 7295-85-4

PubChem CID: 73160

Product Number: Y29700

Max Phase: Preclinical

Molecular Formula: C15H14O6

Molecular Weight: 290.27

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Oc1cc(O)c2c(c1)O[C@@H](c1ccc(O)c(O)c1)[C@H](O)C2

Standard InChI:  InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m1/s1

Standard InChI Key:  PFTAWBLQPZVEMU-HIFRSBDPSA-N

Alternative Forms

  1. Parent:

    ALA200715

    (-)-CATECHIN

Associated Targets(Human)

BACE1 Tchem Beta-secretase 1 (15641 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRD1 Tclin Delta opioid receptor (15096 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Tclin Kappa opioid receptor (16155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGD Tchem 6-phosphogluconate dehydrogenase (58 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Raji (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MET Tclin Hepatocyte growth factor receptor (10718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NEU2 Tbio Sialidase 2 (382 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALB Tchem Serum albumin (2651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (7708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MGAM Tclin Alpha glucosidase (860 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

amyS Alpha-amylase (22 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BMY1 Beta-amylase (20 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabZ Fatty acid synthase (82 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabI Enoyl-acyl-carrier protein reductase (415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabG 3-oxoacyl-acyl-carrier protein reductase (70 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ZWF1 Glucose-6-phosphate 1-dehydrogenase (10 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Cyclooxygenase-1 (5266 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Brugia malayi (1377 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (10718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Solanum lycopersicum (493 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Triticum aestivum (1582 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Arabidopsis thaliana (307 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bassia scoparia (18 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Linaria genistifolia subsp. dalmatica (18 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Centaurea diffusa (18 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Centaurea maculosa (22 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PNLIP Pancreatic triacylglycerol lipase (476 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 290.27Molecular Weight (Monoisotopic): 290.0790AlogP: 1.55#Rotatable Bonds: 1
Polar Surface Area: 110.38Molecular Species: NEUTRALHBA: 6HBD: 5
#RO5 Violations: 0HBA (Lipinski): 6HBD (Lipinski): 5#RO5 Violations (Lipinski): 0
CX Acidic pKa: 9.00CX Basic pKa: CX LogP: 1.80CX LogD: 1.78
Aromatic Rings: 2Heavy Atoms: 21QED Weighted: 0.51Np Likeness Score: 2.30

References

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3. Tasdemir D, Lack G, Brun R, Rüedi P, Scapozza L, Perozzo R..  (2006)  Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.,  49  (11): [PMID:16722653] [10.1021/jm0600545]
4. Katavic PL, Lamb K, Navarro H, Prisinzano TE..  (2007)  Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships.,  70  (8): [PMID:17685652] [10.1021/np070194x]
5. Shin ES, Park J, Shin JM, Cho D, Cho SY, Shin DW, Ham M, Kim JB, Lee TR..  (2008)  Catechin gallates are NADP+-competitive inhibitors of glucose-6-phosphate dehydrogenase and other enzymes that employ NADP+ as a coenzyme.,  16  (7): [PMID:18313308] [10.1016/j.bmc.2008.02.030]
6. Szewczuk LM, Penning TM..  (2004)  Mechanism-based inactivation of COX-1 by red wine m-hydroquinones: a structure-activity relationship study.,  67  (11): [PMID:15568761] [10.1021/np0498410]
7. Takasaki M, Kuroki S, Kozuka M, Konoshima T..  (2001)  New phenylpropanoid esters of sucrose from Polygonum lapathifolium.,  64  (10): [PMID:11678656] [10.1021/np010222q]
8. Larsen CA, Bisson WH, Dashwood RH..  (2009)  Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies.,  52  (21): [PMID:19839593] [10.1021/jm901330e]
9. Arioka S, Sakagami M, Uematsu R, Yamaguchi H, Togame H, Takemoto H, Hinou H, Nishimura S..  (2010)  Potent inhibitor scaffold against Trypanosoma cruzi trans-sialidase.,  18  (4): [PMID:20097567] [10.1016/j.bmc.2009.12.062]
10. Liu Y, Nair MG..  (2010)  An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.,  73  (7): [PMID:20565070] [10.1021/np1000945]
11. Sashidhara KV, Singh SP, Misra S, Gupta J, Misra-Bhattacharya S..  (2012)  Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi.,  50  [PMID:22348826] [10.1016/j.ejmech.2012.01.057]
12. Shen J, Liu X, Tang W, Wang J, Zhang H.  (2012)  Efficient isolation of catechins from green tea and characterization of interaction property of catechins with proteins by HPLCUV/DAD combined with ultrafiltration,  21  (11): [10.1007/s00044-011-9890-z]
13. Rastija V, Medic-Saric M.  (2009)  QSAR modeling of anthocyanins, anthocyanidins and catechins as inhibitors of lipid peroxidation using three-dimensional descriptors,  18  (7): [10.1007/s00044-008-9151-y]
14. Bais HP, Walker TS, Kennan AJ, Stermitz FR, Vivanco JM..  (2003)  Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots.,  51  (4): [PMID:12568546] [10.1021/jf020978a]
15. Ahn JH, Kim ES, Lee C, Kim S, Cho SH, Hwang BY, Lee MK..  (2013)  Chemical constituents from Nelumbo nucifera leaves and their anti-obesity effects.,  23  (12): [PMID:23642481] [10.1016/j.bmcl.2013.04.013]
16. Andreani A, Leoni A, Locatelli A, Morigi R, Rambaldi M, Cervellati R, Greco E, Kondratyuk TP, Park EJ, Huang K, van Breemen RB, Pezzuto JM..  (2013)  Chemopreventive and antioxidant activity of 6-substituted imidazo[2,1-b]thiazoles.,  68  [PMID:23994869] [10.1016/j.ejmech.2013.07.052]
17. Unpublished dataset, 
18. Al-Asri J, Fazekas E, Lehoczki G, Perdih A, Görick C, Melzig MF, Gyémánt G, Wolber G, Mortier J..  (2015)  From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.,  23  (20): [PMID:26395057] [10.1016/j.bmc.2015.09.007]
19. Tomohara K, Ito T, Onikata S, Kato A, Adachi I..  (2017)  Discovery of hyaluronidase inhibitors from natural products and their mechanistic characterization under DMSO-perturbed assay conditions.,  27  (7): [PMID:28202328] [10.1016/j.bmcl.2017.01.083]
20. Tsou LK, Yount JS, Hang HC..  (2017)  Epigallocatechin-3-gallate inhibits bacterial virulence and invasion of host cells.,  25  (11): [PMID:28325635] [10.1016/j.bmc.2017.03.023]
21. Spasov AA, Babkov DA, Osipov DV, Klochkov VG, Prilepskaya DR, Demidov MR, Osyanin VA, Klimochkin YN..  (2019)  Synthesis, in vitro and in vivo evaluation of 2-aryl-4H-chromene and 3-aryl-1H-benzo[f]chromene derivatives as novel α-glucosidase inhibitors.,  29  (1): [PMID:30340897] [10.1016/j.bmcl.2018.10.018]
22. Zima V,Radilová K,Kožíšek M,Albiñana CB,Karlukova E,Brynda J,Fanfrlík J,Flieger M,Hodek J,Weber J,Majer P,Konvalinka J,Machara A.  (2020)  Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors.,  208  [PMID:32883638] [10.1016/j.ejmech.2020.112754]