(-)-Epiafzelechin

Details

• Internal ID: d5f90606-0ecb-42fb-84f9-e5d3a44f4363
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavan-3-ols
• IUPAC Name: (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1
• InChI Key: RSYUFYQTACJFML-UKRRQHHQSA-N
• Popularity: 56 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 24808-04-6
• epi-Afzelechin
• epiafzelechin
• EPIAFZELECHIN (2R,3R)(-)
• CHEMBL159303
• CHEBI:31028
• (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• 2H-1-benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3R)-
• (2R,3R)-2-(4-hydroxyphenyl)chromane-3,5,7-triol
• 2,3-cis-epiafzelechin
• (2R,3R)-epiafzelechin
• Spectrum2_001755
• Spectrum3_001685
• (-)-epi-Afzelechin;Epiafzelechin, (-)-; epi-Afzelechin
• BSPBio_003210
• SPECTRUM202178
• SCHEMBL557061
• SPBio_001890
• KBio3_002430
• DTXSID201316359
• GLXC-17278
• HY-N0943
• BDBM50240892
• CCG-38806
• LMPK12020036
• AKOS032948425
• SDCCGMLS-0066933.P001
• NCGC00178206-01
• AS-79066
• 2-(4-hydroxyphenyl)chromane-3,5,7-triol
• CS-0016076
• E80545
• A930314
• SR-05000002523
• (2R,3R)-2-(4-Hydroxyphenyl)-3,5,7-chromantriol
• Q4690888
• SR-05000002523-1
• BRD-K90607708-001-02-9
• BRD-K90607708-001-03-7
• (2R,3R)-2-(4-Hydroxy-phenyl)-chroman-3,5,7-triol
• (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9429	94.29%
Caco-2	-	0.8083	80.83%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4617	46.17%
OATP2B1 inhibitior	-	0.5941	59.41%
OATP1B1 inhibitior	-	0.7739	77.39%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8517	85.17%
P-glycoprotein inhibitior	-	0.9041	90.41%
P-glycoprotein substrate	-	0.9280	92.80%
CYP3A4 substrate	-	0.5560	55.60%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	+	0.6005	60.05%
CYP3A4 inhibition	-	0.8168	81.68%
CYP2C9 inhibition	-	0.6458	64.58%
CYP2C19 inhibition	-	0.6115	61.15%
CYP2D6 inhibition	-	0.9034	90.34%
CYP1A2 inhibition	-	0.8445	84.45%
CYP2C8 inhibition	+	0.4602	46.02%
CYP inhibitory promiscuity	-	0.6461	64.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6008	60.08%
Eye corrosion	-	0.9900	99.00%
Eye irritation	+	0.9144	91.44%
Skin irritation	-	0.5579	55.79%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5835	58.35%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.7662	76.62%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.4603	46.03%
Acute Oral Toxicity (c)	IV	0.4540	45.40%
Estrogen receptor binding	-	0.5727	57.27%
Androgen receptor binding	+	0.7050	70.50%
Thyroid receptor binding	+	0.6967	69.67%
Glucocorticoid receptor binding	+	0.5440	54.40%
Aromatase binding	+	0.6578	65.78%
PPAR gamma	+	0.7460	74.60%
Honey bee toxicity	-	0.8770	87.70%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.6963	69.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL221	P23219	Cyclooxygenase-1	6400 nM; 15000 nM	IC50; IC50	PMID: 11858749; PMID: 16038536

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.71%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.00%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.97%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.32%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.92%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.77%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.96%	93.40%
CHEMBL3194	P02766	Transthyretin	83.51%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	81.37%	98.35%
CHEMBL2535	P11166	Glucose transporter	81.10%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.18%	94.45%

Plants that contains it

• Actinidia chinensis
• Aiouea hammeliana
• Artocarpus lacucha
• Bauhinia racemosa
• Calophyllum apetalum
• Camellia sinensis
• Canthium berberidifolium
• Cassia fistula
• Cassia javanica
• Cassia roxburghii
• Cassia sieberiana
• Celastrus orbiculatus
• Crateva religiosa
• Dicranopteris pedata
• Ephedra distachya
• Ephedra equisetina
• Ephedra intermedia
• Ephedra sinica
• Ficus cordata
• Larix gmelinii
• Madhuca pasquieri
• Phyllanthus emblica
• Senegalia catechu
• Tsuga chinensis
• Typha capensis
• Wisteria floribunda
• Xanthoceras sorbifolium
• Ziziphus jujuba

Cross-Links

• PubChem: 443639
• NPASS: NPC278552
• ChEMBL: CHEMBL159303
• LOTUS: LTS0203074
• wikiData: Q4690888