6,8-Dihydroxy-5-methylbenzo[a]phenalen-7-one

Details

• Internal ID: e9035169-26d5-4f32-9bfc-0ca0947a6e09
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: 6,8-dihydroxy-5-methylbenzo[a]phenalen-7-one
• SMILES (Canonical): CC1=CC2=C3C(=CC=C2)C4=C(C(=CC=C4)O)C(=O)C3=C1O
• SMILES (Isomeric): CC1=CC2=C3C(=CC=C2)C4=C(C(=CC=C4)O)C(=O)C3=C1O
• InChI: InChI=1S/C18H12O3/c1-9-8-10-4-2-5-11-12-6-3-7-13(19)15(12)18(21)16(14(10)11)17(9)20/h2-8,19-20H,1H3
• InChI Key: LGHMJRHHYVWCBH-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₂O₃
• Molecular Weight: 276.30 g/mol
• Exact Mass: 276.078644241 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.77
• H-Bond Acceptor: 3
• 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	+	1.0000	100.00%
Caco-2	+	0.7880	78.80%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8843	88.43%
OATP2B1 inhibitior	-	0.7151	71.51%
OATP1B1 inhibitior	+	0.9010	90.10%
OATP1B3 inhibitior	+	0.9730	97.30%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5159	51.59%
P-glycoprotein inhibitior	-	0.8766	87.66%
P-glycoprotein substrate	-	0.9201	92.01%
CYP3A4 substrate	-	0.5308	53.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.8821	88.21%
CYP2C9 inhibition	+	0.8120	81.20%
CYP2C19 inhibition	+	0.7439	74.39%
CYP2D6 inhibition	-	0.8939	89.39%
CYP1A2 inhibition	+	0.9712	97.12%
CYP2C8 inhibition	-	0.7539	75.39%
CYP inhibitory promiscuity	+	0.5419	54.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7735	77.35%
Carcinogenicity (trinary)	Non-required	0.4826	48.26%
Eye corrosion	-	0.9811	98.11%
Eye irritation	+	0.8206	82.06%
Skin irritation	+	0.8323	83.23%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	+	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8211	82.11%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.5776	57.76%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6163	61.63%
Acute Oral Toxicity (c)	III	0.7249	72.49%
Estrogen receptor binding	+	0.8989	89.89%
Androgen receptor binding	+	0.6909	69.09%
Thyroid receptor binding	+	0.6405	64.05%
Glucocorticoid receptor binding	+	0.9471	94.71%
Aromatase binding	+	0.7350	73.50%
PPAR gamma	+	0.8795	87.95%
Honey bee toxicity	-	0.9576	95.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9791	97.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.97%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.74%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.53%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	93.25%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.62%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	90.17%	91.49%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.62%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.36%	94.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	88.67%	96.67%
CHEMBL1937	Q92769	Histone deacetylase 2	88.51%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.31%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.10%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.10%	96.95%
CHEMBL4530	P00488	Coagulation factor XIII	81.13%	96.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.09%	85.11%

Plants that contains it

• Picramnia latifolia

Cross-Links

• PubChem: 44575531
• LOTUS: LTS0071312
• wikiData: Q105151354