2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,7-triol

Details

• Internal ID: a02583b1-cf0a-4cd8-bbe8-7c9a04da58a7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Leucoanthocyanidins
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,7-triol
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(C3=C(O2)C=C(C=C3)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2C(C(C3=C(O2)C=C(C=C3)O)O)O)O)O
• InChI: InChI=1S/C15H14O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,13-20H
• InChI Key: OFZBQQUVMQGHDJ-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₆
• Molecular Weight: 290.27 g/mol
• Exact Mass: 290.07903816 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• 3,3',4,4',7-flavanpentol
• SCHEMBL14228832
• FT-0772305

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9373	93.73%
Caco-2	-	0.9281	92.81%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6922	69.22%
OATP2B1 inhibitior	-	0.5756	57.56%
OATP1B1 inhibitior	+	0.9440	94.40%
OATP1B3 inhibitior	+	0.9930	99.30%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9017	90.17%
P-glycoprotein inhibitior	-	0.9146	91.46%
P-glycoprotein substrate	-	0.9338	93.38%
CYP3A4 substrate	-	0.5389	53.89%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	+	0.3999	39.99%
CYP3A4 inhibition	-	0.8362	83.62%
CYP2C9 inhibition	+	0.8918	89.18%
CYP2C19 inhibition	-	0.5999	59.99%
CYP2D6 inhibition	-	0.9008	90.08%
CYP1A2 inhibition	+	0.8639	86.39%
CYP2C8 inhibition	+	0.5687	56.87%
CYP inhibitory promiscuity	+	0.5761	57.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5357	53.57%
Eye corrosion	-	0.9871	98.71%
Eye irritation	+	0.9610	96.10%
Skin irritation	+	0.5803	58.03%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6627	66.27%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7870	78.70%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7801	78.01%
Acute Oral Toxicity (c)	II	0.6941	69.41%
Estrogen receptor binding	-	0.5961	59.61%
Androgen receptor binding	-	0.5488	54.88%
Thyroid receptor binding	+	0.7880	78.80%
Glucocorticoid receptor binding	+	0.6460	64.60%
Aromatase binding	+	0.7063	70.63%
PPAR gamma	+	0.7114	71.14%
Honey bee toxicity	-	0.8191	81.91%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9072	90.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.17%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.19%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.72%	96.09%
CHEMBL3194	P02766	Transthyretin	86.73%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	86.70%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.21%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.03%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.03%	95.56%
CHEMBL2535	P11166	Glucose transporter	84.68%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	81.02%	96.42%
CHEMBL2581	P07339	Cathepsin D	80.28%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.12%	85.14%

Plants that contains it

• Acacia baileyana
• Acacia crombiei
• Acacia pubescens
• Gleditsia japonica

Cross-Links

• PubChem: 3508976
• LOTUS: LTS0235958
• wikiData: Q105191475