(+)-Epitaxifolin

Details

• Internal ID: 01398d1a-c8be-460d-a6bf-7322bb346e9b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2S,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1[C@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• InChI: InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15-/m0/s1
• InChI Key: CXQWRCVTCMQVQX-GJZGRUSLSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25 g/mol
• Exact Mass: 304.05830272 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• cis-Dihydroquercetin
• (2S,3R)-Epitaxifolin
• (+)-(2S,3R)-epitaxifolin
• CHEBI:32330
• (2S,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one
• 153666-25-2
• Lopac-T-4512
• (2S,3R)-dihydroquercetin
• CHEMBL9249
• rel-(2R,3S)-Epitaxifolin
• SCHEMBL17668129
• (2S,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• NCGC00016024-01
• Q27114878
• 329182-30-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9071	90.71%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5892	58.92%
OATP2B1 inhibitior	-	0.6726	67.26%
OATP1B1 inhibitior	+	0.9649	96.49%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8847	88.47%
P-glycoprotein inhibitior	-	0.8944	89.44%
P-glycoprotein substrate	-	0.9736	97.36%
CYP3A4 substrate	-	0.5317	53.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7991	79.91%
CYP3A4 inhibition	+	0.6951	69.51%
CYP2C9 inhibition	-	0.5823	58.23%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9287	92.87%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.6060	60.60%
CYP inhibitory promiscuity	+	0.5822	58.22%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6750	67.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9821	98.21%
Skin irritation	+	0.5835	58.35%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7322	73.22%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6337	63.37%
Acute Oral Toxicity (c)	II	0.7348	73.48%
Estrogen receptor binding	+	0.6059	60.59%
Androgen receptor binding	+	0.6826	68.26%
Thyroid receptor binding	+	0.6958	69.58%
Glucocorticoid receptor binding	+	0.7493	74.93%
Aromatase binding	+	0.6475	64.75%
PPAR gamma	+	0.7044	70.44%
Honey bee toxicity	-	0.8494	84.94%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9124	91.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	12589.3 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	12589.3 nM	Potency	via CMAUP
CHEMBL2326	P43166	Carbonic anhydrase VII	493.1 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	32.5 nM	Ki	via Super-PRED
CHEMBL3356	P05177	Cytochrome P450 1A2	15848.93 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	5011.9 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	31.6 nM; 31.6 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	1584.9 nM; 1584.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.51%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.02%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.37%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.14%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.12%	99.15%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.44%	96.12%
CHEMBL3401	O75469	Pregnane X receptor	86.15%	94.73%
CHEMBL3194	P02766	Transthyretin	86.06%	90.71%
CHEMBL2581	P07339	Cathepsin D	83.85%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.64%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.26%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.91%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.86%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.72%	93.40%

Plants that contains it

• Anastatica hierochuntica
• Morus alba
• Nelumbo nucifera
• Smilax china
• Vitis vinifera

Cross-Links

• PubChem: 443758
• NPASS: NPC9743
• ChEMBL: CHEMBL9249
• LOTUS: LTS0096746
• wikiData: Q27114878