4,7-Dihydroxy-2,3-methylenedioxy-9,10-dihydro-phenanthrene

Details

• Internal ID: 9ed220b0-9747-4107-abe8-6cfd44c32ad9
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: 5,6-dihydronaphtho[2,1-f][1,3]benzodioxole-3,11-diol
• SMILES (Canonical): C1CC2=C(C=CC(=C2)O)C3=C(C4=C(C=C31)OCO4)O
• SMILES (Isomeric): C1CC2=C(C=CC(=C2)O)C3=C(C4=C(C=C31)OCO4)O
• InChI: InChI=1S/C15H12O4/c16-10-3-4-11-8(5-10)1-2-9-6-12-15(19-7-18-12)14(17)13(9)11/h3-6,16-17H,1-2,7H2
• InChI Key: QPSCKIQSZZPZQX-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25 g/mol
• Exact Mass: 256.07355886 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9440	94.40%
Caco-2	+	0.6408	64.08%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7737	77.37%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8576	85.76%
OATP1B3 inhibitior	+	0.9213	92.13%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5426	54.26%
P-glycoprotein inhibitior	-	0.9299	92.99%
P-glycoprotein substrate	-	0.8933	89.33%
CYP3A4 substrate	+	0.5121	51.21%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	+	0.3753	37.53%
CYP3A4 inhibition	-	0.6172	61.72%
CYP2C9 inhibition	+	0.7019	70.19%
CYP2C19 inhibition	+	0.5471	54.71%
CYP2D6 inhibition	+	0.5395	53.95%
CYP1A2 inhibition	+	0.7891	78.91%
CYP2C8 inhibition	+	0.5289	52.89%
CYP inhibitory promiscuity	+	0.6092	60.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Warning	0.3914	39.14%
Eye corrosion	-	0.9849	98.49%
Eye irritation	+	0.9432	94.32%
Skin irritation	-	0.6483	64.83%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6439	64.39%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7795	77.95%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5731	57.31%
Acute Oral Toxicity (c)	III	0.5602	56.02%
Estrogen receptor binding	+	0.8311	83.11%
Androgen receptor binding	+	0.7971	79.71%
Thyroid receptor binding	+	0.6188	61.88%
Glucocorticoid receptor binding	+	0.6397	63.97%
Aromatase binding	+	0.5381	53.81%
PPAR gamma	+	0.8707	87.07%
Honey bee toxicity	-	0.9145	91.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.8640	86.40%

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	99.30%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.66%	91.49%
CHEMBL242	Q92731	Estrogen receptor beta	96.84%	98.35%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	93.02%	82.67%
CHEMBL2581	P07339	Cathepsin D	90.38%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.58%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.37%	86.33%
CHEMBL5145	P15056	Serine/threonine-protein kinase B-raf	85.93%	97.90%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.88%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.53%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.96%	95.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.80%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.04%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.31%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.76%	93.10%

Plants that contains it

• Bulbophyllum andersonii

Cross-Links

• PubChem: 15081425
• LOTUS: LTS0102718
• wikiData: Q105225566