3,4-Dihydro-2,6,9-trihydroxy-8-methyl-1(2 h)-anthracenone

Details

• Internal ID: c93e8dfa-48d6-4b74-a6ae-efd7e72bfaec
• Taxonomy: Benzenoids > Anthracenes
• IUPAC Name: 2,6,9-trihydroxy-8-methyl-3,4-dihydro-2H-anthracen-1-one
• SMILES (Canonical): CC1=CC(=CC2=CC3=C(C(=O)C(CC3)O)C(=C12)O)O
• SMILES (Isomeric): CC1=CC(=CC2=CC3=C(C(=O)C(CC3)O)C(=C12)O)O
• InChI: InChI=1S/C15H14O4/c1-7-4-10(16)6-9-5-8-2-3-11(17)14(18)13(8)15(19)12(7)9/h4-6,11,16-17,19H,2-3H2,1H3
• InChI Key: INDWVRYSFIGJBR-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	+	0.6301	63.01%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8434	84.34%
OATP2B1 inhibitior	-	0.7087	70.87%
OATP1B1 inhibitior	+	0.9291	92.91%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9571	95.71%
BSEP inhibitior	-	0.8062	80.62%
P-glycoprotein inhibitior	-	0.9710	97.10%
P-glycoprotein substrate	-	0.8646	86.46%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8012	80.12%
CYP3A4 inhibition	-	0.8402	84.02%
CYP2C9 inhibition	-	0.6159	61.59%
CYP2C19 inhibition	-	0.6464	64.64%
CYP2D6 inhibition	-	0.8928	89.28%
CYP1A2 inhibition	+	0.8950	89.50%
CYP2C8 inhibition	-	0.6970	69.70%
CYP inhibitory promiscuity	-	0.8541	85.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5121	51.21%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.6460	64.60%
Skin irritation	+	0.5439	54.39%
Skin corrosion	-	0.8634	86.34%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6382	63.82%
Micronuclear	-	0.5441	54.41%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.7346	73.46%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6001	60.01%
Acute Oral Toxicity (c)	III	0.7248	72.48%
Estrogen receptor binding	+	0.7466	74.66%
Androgen receptor binding	+	0.6483	64.83%
Thyroid receptor binding	-	0.7381	73.81%
Glucocorticoid receptor binding	+	0.7130	71.30%
Aromatase binding	-	0.7760	77.60%
PPAR gamma	+	0.6960	69.60%
Honey bee toxicity	-	0.9269	92.69%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8957	89.57%

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	97.62%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.17%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.14%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.45%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.76%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.73%	89.00%
CHEMBL217	P14416	Dopamine D2 receptor	83.74%	95.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.91%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.72%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.30%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	82.21%	91.49%
CHEMBL4581	P52732	Kinesin-like protein 1	81.50%	93.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.91%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.90%	86.33%

Plants that contains it

• Gasteria obliqua

Cross-Links

• PubChem: 101690773
• LOTUS: LTS0169000
• wikiData: Q105116167