(6S,8R)-6-(4-hydroxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene-8,9-diol

Details

• Internal ID: c9afae56-0da8-4376-940b-414ce0c781f4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavan-4-ols
• IUPAC Name: (6S,8R)-6-(4-hydroxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene-8,9-diol
• SMILES (Canonical): C1C(C2=C(C3=C(C=C2OC1C4=CC=C(C=C4)O)OCO3)O)O
• SMILES (Isomeric): C1[C@H](C2=C(C3=C(C=C2O[C@@H]1C4=CC=C(C=C4)O)OCO3)O)O
• InChI: InChI=1S/C16H14O6/c17-9-3-1-8(2-4-9)11-5-10(18)14-12(22-11)6-13-16(15(14)19)21-7-20-13/h1-4,6,10-11,17-19H,5,7H2/t10-,11+/m1/s1
• InChI Key: IACPLVRRLSRKDF-MNOVXSKESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 88.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8938	89.38%
Caco-2	-	0.6905	69.05%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6204	62.04%
OATP2B1 inhibitior	-	0.5928	59.28%
OATP1B1 inhibitior	+	0.8803	88.03%
OATP1B3 inhibitior	+	0.8653	86.53%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7831	78.31%
P-glycoprotein inhibitior	-	0.8311	83.11%
P-glycoprotein substrate	-	0.9019	90.19%
CYP3A4 substrate	-	0.5145	51.45%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	+	0.4502	45.02%
CYP3A4 inhibition	+	0.5962	59.62%
CYP2C9 inhibition	-	0.6892	68.92%
CYP2C19 inhibition	-	0.7612	76.12%
CYP2D6 inhibition	-	0.5839	58.39%
CYP1A2 inhibition	-	0.7397	73.97%
CYP2C8 inhibition	+	0.4873	48.73%
CYP inhibitory promiscuity	+	0.5254	52.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4767	47.67%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.5935	59.35%
Skin irritation	-	0.7205	72.05%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6889	68.89%
Micronuclear	+	0.7259	72.59%
Hepatotoxicity	-	0.6966	69.66%
skin sensitisation	-	0.8604	86.04%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6561	65.61%
Acute Oral Toxicity (c)	III	0.5673	56.73%
Estrogen receptor binding	+	0.6804	68.04%
Androgen receptor binding	+	0.6810	68.10%
Thyroid receptor binding	+	0.7703	77.03%
Glucocorticoid receptor binding	+	0.6987	69.87%
Aromatase binding	+	0.5881	58.81%
PPAR gamma	+	0.8482	84.82%
Honey bee toxicity	-	0.8693	86.93%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.6685	66.85%

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	97.79%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.52%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.05%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.42%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.80%	89.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.79%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.48%	93.40%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.62%	82.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.34%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.33%	95.56%
CHEMBL4208	P20618	Proteasome component C5	80.93%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.37%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.04%	95.89%

Plants that contains it

• Pycnanthus angolensis

Cross-Links

• PubChem: 162885845
• LOTUS: LTS0207179
• wikiData: Q105036023