2-(3,4-Dihydroxyphenyl)-3,4,7,8-chromanetetrol

Details

• Internal ID: fe45b4e4-b945-403d-99e2-a97dc3eabc5b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Leucoanthocyanidins
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,7,8-tetrol
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(C3=C(O2)C(=C(C=C3)O)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)O
• InChI: InChI=1S/C15H14O7/c16-8-3-1-6(5-10(8)18)14-13(21)11(19)7-2-4-9(17)12(20)15(7)22-14/h1-5,11,13-14,16-21H
• InChI Key: JEUXGAUBSWADEA-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.27 g/mol
• Exact Mass: 306.07395278 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 1

Synonyms

• MEGxp0_001312
• SCHEMBL2146446
• ACon1_001155
• NCGC00169623-01
• 7,8,3',4'-Tetrahydroxyflavan-3,4-diol
• 2-(3,4-Dihydroxyphenyl)-3,4,7,8-chromanetetrol
• 2-(3,4-dihydroxyphenyl)chromane-3,4,7,8-tetrol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9373	93.73%
Caco-2	-	0.9424	94.24%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6922	69.22%
OATP2B1 inhibitior	-	0.5665	56.65%
OATP1B1 inhibitior	+	0.9397	93.97%
OATP1B3 inhibitior	+	0.9930	99.30%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9261	92.61%
P-glycoprotein inhibitior	-	0.9129	91.29%
P-glycoprotein substrate	-	0.9460	94.60%
CYP3A4 substrate	-	0.5560	55.60%
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	+	0.4567	45.67%
CYP inhibitory promiscuity	+	0.5761	57.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5357	53.57%
Eye corrosion	-	0.9871	98.71%
Eye irritation	+	0.9213	92.13%
Skin irritation	+	0.5803	58.03%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6530	65.30%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.7870	78.70%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8673	86.73%
Acute Oral Toxicity (c)	II	0.6941	69.41%
Estrogen receptor binding	-	0.6398	63.98%
Androgen receptor binding	+	0.6183	61.83%
Thyroid receptor binding	+	0.7723	77.23%
Glucocorticoid receptor binding	+	0.7233	72.33%
Aromatase binding	+	0.6443	64.43%
PPAR gamma	+	0.6386	63.86%
Honey bee toxicity	-	0.8773	87.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
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	98.97%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.40%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.92%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.89%	89.00%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	86.48%	96.42%
CHEMBL3401	O75469	Pregnane X receptor	86.43%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.39%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.79%	95.56%
CHEMBL3194	P02766	Transthyretin	83.50%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.08%	97.09%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	82.84%	83.10%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.61%	95.89%

Plants that contains it

• Acacia confusa
• Acacia excelsa
• Acacia melanoxylon
• Prosopis glandulosa

Cross-Links

• PubChem: 494064
• LOTUS: LTS0220721
• wikiData: Q105126426