2,6-dihydroxy-1,1,7-trimethyl-10,10a-dihydro-2H-phenanthrene-3,9-dione

Details

• Internal ID: 5e4682ef-34f8-4d39-b708-ccf69d57a1bb
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: 2,6-dihydroxy-1,1,7-trimethyl-10,10a-dihydro-2H-phenanthrene-3,9-dione
• SMILES (Canonical): CC1=CC2=C(C=C1O)C3=CC(=O)C(C(C3CC2=O)(C)C)O
• SMILES (Isomeric): CC1=CC2=C(C=C1O)C3=CC(=O)C(C(C3CC2=O)(C)C)O
• InChI: InChI=1S/C17H18O4/c1-8-4-11-9(5-13(8)18)10-6-15(20)16(21)17(2,3)12(10)7-14(11)19/h4-6,12,16,18,21H,7H2,1-3H3
• InChI Key: LBNRPGWLEIKUBN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₄
• Molecular Weight: 286.32 g/mol
• Exact Mass: 286.12050905 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.26
• 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	+	0.9963	99.63%
Caco-2	+	0.5289	52.89%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8517	85.17%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8865	88.65%
OATP1B3 inhibitior	+	0.9328	93.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8619	86.19%
P-glycoprotein inhibitior	-	0.9665	96.65%
P-glycoprotein substrate	-	0.7378	73.78%
CYP3A4 substrate	+	0.5814	58.14%
CYP2C9 substrate	-	0.7282	72.82%
CYP2D6 substrate	-	0.8368	83.68%
CYP3A4 inhibition	-	0.7294	72.94%
CYP2C9 inhibition	+	0.6440	64.40%
CYP2C19 inhibition	+	0.6452	64.52%
CYP2D6 inhibition	-	0.5375	53.75%
CYP1A2 inhibition	+	0.7422	74.22%
CYP2C8 inhibition	-	0.8182	81.82%
CYP inhibitory promiscuity	+	0.6242	62.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9311	93.11%
Carcinogenicity (trinary)	Non-required	0.5958	59.58%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8508	85.08%
Skin irritation	-	0.5661	56.61%
Skin corrosion	-	0.8987	89.87%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7237	72.37%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	+	0.6013	60.13%
skin sensitisation	-	0.5623	56.23%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6535	65.35%
Acute Oral Toxicity (c)	III	0.7481	74.81%
Estrogen receptor binding	+	0.6074	60.74%
Androgen receptor binding	-	0.4834	48.34%
Thyroid receptor binding	+	0.5269	52.69%
Glucocorticoid receptor binding	+	0.8097	80.97%
Aromatase binding	+	0.5297	52.97%
PPAR gamma	+	0.6472	64.72%
Honey bee toxicity	-	0.8583	85.83%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9957	99.57%

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	98.85%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.45%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.01%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.10%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.55%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.35%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.36%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.89%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.57%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.34%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.56%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.53%	95.89%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.86%	94.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.17%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.06%	86.33%

Plants that contains it

• Trigonostemon xyphophylloides

Cross-Links

• PubChem: 56677956
• LOTUS: LTS0164978
• wikiData: Q105149490