(2R)-2-hydroxy-2-methyl-3,4-dihydro-1H-benzo[a]anthracene-7,12-dione

Details

• Internal ID: 1d666320-f55c-40e9-81ad-7d37dd5263ff
• Taxonomy: Phenylpropanoids and polyketides > Angucyclines
• IUPAC Name: (2R)-2-hydroxy-2-methyl-3,4-dihydro-1H-benzo[a]anthracene-7,12-dione
• SMILES (Canonical): CC1(CCC2=C(C1)C3=C(C=C2)C(=O)C4=CC=CC=C4C3=O)O
• SMILES (Isomeric): C[C@]1(CCC2=C(C1)C3=C(C=C2)C(=O)C4=CC=CC=C4C3=O)O
• InChI: InChI=1S/C19H16O3/c1-19(22)9-8-11-6-7-14-16(15(11)10-19)18(21)13-5-3-2-4-12(13)17(14)20/h2-7,22H,8-10H2,1H3/t19-/m1/s1
• InChI Key: SIJURHHKUFYDRK-LJQANCHMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₃
• Molecular Weight: 292.30 g/mol
• Exact Mass: 292.109944368 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• 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	+	0.5157	51.57%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8810	88.10%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9218	92.18%
OATP1B3 inhibitior	+	0.9708	97.08%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5554	55.54%
P-glycoprotein inhibitior	-	0.7324	73.24%
P-glycoprotein substrate	-	0.8073	80.73%
CYP3A4 substrate	+	0.5409	54.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7844	78.44%
CYP3A4 inhibition	-	0.8019	80.19%
CYP2C9 inhibition	-	0.8484	84.84%
CYP2C19 inhibition	-	0.8932	89.32%
CYP2D6 inhibition	-	0.9090	90.90%
CYP1A2 inhibition	-	0.7428	74.28%
CYP2C8 inhibition	-	0.9365	93.65%
CYP inhibitory promiscuity	-	0.9816	98.16%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8411	84.11%
Carcinogenicity (trinary)	Non-required	0.5719	57.19%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.5708	57.08%
Skin irritation	-	0.5829	58.29%
Skin corrosion	-	0.9224	92.24%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3989	39.89%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5541	55.41%
skin sensitisation	-	0.8553	85.53%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6330	63.30%
Acute Oral Toxicity (c)	III	0.7458	74.58%
Estrogen receptor binding	+	0.8380	83.80%
Androgen receptor binding	+	0.7964	79.64%
Thyroid receptor binding	-	0.5105	51.05%
Glucocorticoid receptor binding	+	0.8910	89.10%
Aromatase binding	+	0.6395	63.95%
PPAR gamma	+	0.8871	88.71%
Honey bee toxicity	-	0.8976	89.76%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9900	99.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.22%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.80%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.39%	95.56%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	93.33%	85.94%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.04%	82.69%
CHEMBL1907	P15144	Aminopeptidase N	86.75%	93.31%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.03%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.31%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.45%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.93%	86.33%

Plants that contains it

• Stereospermum acuminatissimum
• Stereospermum zenkeri

Cross-Links

• PubChem: 132987765
• LOTUS: LTS0157968
• wikiData: Q105253795