3,4-Dimethoxyphenanthrene-2,5-Diol

Details

• Internal ID: d6bd4fcc-d28b-485e-857e-a83155b26dd7
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Phenanthrols
• IUPAC Name: 3,4-dimethoxyphenanthrene-2,5-diol
• SMILES (Canonical): COC1=C(C=C2C=CC3=C(C2=C1OC)C(=CC=C3)O)O
• SMILES (Isomeric): COC1=C(C=C2C=CC3=C(C2=C1OC)C(=CC=C3)O)O
• InChI: InChI=1S/C16H14O4/c1-19-15-12(18)8-10-7-6-9-4-3-5-11(17)13(9)14(10)16(15)20-2/h3-8,17-18H,1-2H3
• InChI Key: CXPHYDHTAOQSNC-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28 g/mol
• Exact Mass: 270.08920892 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEMBL414129
• 2,5-phenanthrenediol, 3,4-dimethoxy-
• InChI=1/C16H14O4/c1-19-15-12(18)8-10-7-6-9-4-3-5-11(17)13(9)14(10)16(15)20-2/h3-8,17-18H,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9886	98.86%
Caco-2	+	0.6787	67.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7456	74.56%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9169	91.69%
OATP1B3 inhibitior	+	0.9690	96.90%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5573	55.73%
P-glycoprotein inhibitior	-	0.8333	83.33%
P-glycoprotein substrate	-	0.9497	94.97%
CYP3A4 substrate	-	0.6189	61.89%
CYP2C9 substrate	-	0.7933	79.33%
CYP2D6 substrate	+	0.4916	49.16%
CYP3A4 inhibition	-	0.7576	75.76%
CYP2C9 inhibition	-	0.5823	58.23%
CYP2C19 inhibition	+	0.6612	66.12%
CYP2D6 inhibition	-	0.7451	74.51%
CYP1A2 inhibition	+	0.9474	94.74%
CYP2C8 inhibition	-	0.6196	61.96%
CYP inhibitory promiscuity	+	0.6410	64.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8228	82.28%
Carcinogenicity (trinary)	Non-required	0.4930	49.30%
Eye corrosion	-	0.9756	97.56%
Eye irritation	+	0.9057	90.57%
Skin irritation	-	0.5481	54.81%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	+	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6061	60.61%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7934	79.34%
Respiratory toxicity	-	0.8111	81.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5920	59.20%
Acute Oral Toxicity (c)	III	0.5042	50.42%
Estrogen receptor binding	+	0.9110	91.10%
Androgen receptor binding	+	0.6130	61.30%
Thyroid receptor binding	+	0.8192	81.92%
Glucocorticoid receptor binding	+	0.8053	80.53%
Aromatase binding	+	0.7661	76.61%
PPAR gamma	+	0.6855	68.55%
Honey bee toxicity	-	0.9573	95.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9532	95.32%

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	96.18%	91.11%
CHEMBL2535	P11166	Glucose transporter	91.08%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.37%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.53%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.17%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	87.99%	91.49%
CHEMBL3959	P16083	Quinone reductase 2	85.73%	89.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.60%	99.15%
CHEMBL2581	P07339	Cathepsin D	85.52%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.90%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	82.90%	94.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.45%	93.99%
CHEMBL1907	P15144	Aminopeptidase N	80.36%	93.31%
CHEMBL3401	O75469	Pregnane X receptor	80.18%	94.73%

Plants that contains it

• Dendrobium nobile
• Maxillaria densa

Cross-Links

• PubChem: 640646
• NPASS: NPC218131
• LOTUS: LTS0101017
• wikiData: Q104971972