(+)-Catechin Hydrate

Details

• Internal ID: 67d48ed4-6d35-4646-b3e5-08855df0039c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol;hydrate
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O.O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O.O
• InChI: InChI=1S/C15H14O6.H2O/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;1H2/t13-,15+;/m0./s1
• InChI Key: OFUMQWOJBVNKLR-NQQJLSKUSA-N
• Popularity: 184 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₇
• Molecular Weight: 308.28 g/mol
• Exact Mass: 308.08960285 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• Catechin hydrate
• 225937-10-0
• (+)-catechin monohydrate
• (2R,3S)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol hydrate
• 88191-48-4
• (+)-Cyanidol-3
• CHEBI:58994
• (2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol monohydrate
• (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
• (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol;hydrate
• D-Catechin hydrate
• MLS001056745
• (2R,3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol--water (1/1)
• 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol monohydrate, (2R-trans)-
• 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, monohydrate, (2R-trans)-
• SMR000326724
• MFCD00149354
• Cianidanol (JAN/INN)
• (+/-)-Catechin (hydrate)
• SCHEMBL133974
• CHEMBL1256783
• DTXSID801007988
• HMS2233I24
• HMS3649E10
• MFCD00150865
• AKOS016843747
• DS-2787
• (+)-3,3',4',5,7-Flavanpentol . H2O
• D00200
• S00276
• (+)-Catechin hydrate, >=98% (HPLC), powder
• W-104471
• (+/-)-Catechin hydrate, purum, >=96.0% (HPLC)
• Q27126384
• SR-01000075742-11
• SR-01000075742-15
• (+)-Catechin hydrate, >=96.0% (sum of enantiomers, HPLC)
• (+/-)-Catechin hydrate, primary pharmaceutical reference standard
• (2R,3S)-2-(3,4-Dihydroxyphenyl)-chroman-3,5,7-triol hydrate
• (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol hydrate
• 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, monohydrate, (2R,3S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8911	89.11%
Caco-2	-	0.9406	94.06%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4440	44.40%
OATP2B1 inhibitior	-	0.5776	57.76%
OATP1B1 inhibitior	+	0.8767	87.67%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9228	92.28%
P-glycoprotein inhibitior	-	0.9411	94.11%
P-glycoprotein substrate	-	0.9512	95.12%
CYP3A4 substrate	-	0.5413	54.13%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	+	0.5322	53.22%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9041	90.41%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.4615	46.15%
CYP inhibitory promiscuity	-	0.8170	81.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5825	58.25%
Eye corrosion	-	0.9888	98.88%
Eye irritation	+	0.9629	96.29%
Skin irritation	-	0.6065	60.65%
Skin corrosion	-	0.9227	92.27%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4678	46.78%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7537	75.37%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6183	61.83%
Acute Oral Toxicity (c)	IV	0.6433	64.33%
Estrogen receptor binding	-	0.6719	67.19%
Androgen receptor binding	+	0.6638	66.38%
Thyroid receptor binding	+	0.7658	76.58%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	+	0.6008	60.08%
PPAR gamma	+	0.6832	68.32%
Honey bee toxicity	-	0.8050	80.50%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.7385	73.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5979	P05186	Alkaline phosphatase, tissue-nonspecific isozyme	37100 nM	IC50	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	28183.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	19952.6 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	22387.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.39%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.02%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.80%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.87%	97.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.65%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.31%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.65%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.57%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.35%	93.40%
CHEMBL3194	P02766	Transthyretin	84.35%	90.71%
CHEMBL2535	P11166	Glucose transporter	82.95%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	81.78%	94.73%
CHEMBL2581	P07339	Cathepsin D	80.48%	98.95%
CHEMBL4208	P20618	Proteasome component C5	80.01%	90.00%

Plants that contains it

• Ginkgo biloba

Cross-Links

• PubChem: 107957
• NPASS: NPC78770
• ChEMBL: CHEMBL1256783