1-(4-Hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol

Details

• Internal ID: 77baeddd-1586-42a9-bc2b-310fa26d16cc
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: 1-[(4-hydroxyphenyl)methyl]-4-methoxy-9,10-dihydrophenanthrene-2,7-diol
• SMILES (Canonical): COC1=C2C(=C(C(=C1)O)CC3=CC=C(C=C3)O)CCC4=C2C=CC(=C4)O
• SMILES (Isomeric): COC1=C2C(=C(C(=C1)O)CC3=CC=C(C=C3)O)CCC4=C2C=CC(=C4)O
• InChI: InChI=1S/C22H20O4/c1-26-21-12-20(25)19(10-13-2-5-15(23)6-3-13)18-8-4-14-11-16(24)7-9-17(14)22(18)21/h2-3,5-7,9,11-12,23-25H,4,8,10H2,1H3
• InChI Key: XNPQRYUNKPQOPF-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₄
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.13615911 g/mol
• Topological Polar Surface Area (TPSA): 69.90 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.17
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 2,7-Phenanthrenediol, 9,10-dihydro-1-[(4-hydroxyphenyl)methyl]-4-methoxy-
• CHEMBL3911758
• SCHEMBL23753970
• DTXSID901152154
• D85194
• 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol
• 1-(4-HYDROXYBENZYL)-4-METHOXY-9,10-DIHYDROPENANTHRENE-2,7-DIOL
• 2,7-dihydroxy-1-(p-hydroxylbenzyl)-4-methoxy-9,10-dihydrophenanthrene
• 9,10-Dihydro-1-[(4-hydroxyphenyl)methyl]-4-methoxy-2,7-phenanthrenediol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9818	98.18%
Caco-2	-	0.6339	63.39%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.9034	90.34%
OATP2B1 inhibitior	-	0.5701	57.01%
OATP1B1 inhibitior	+	0.8021	80.21%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8861	88.61%
P-glycoprotein inhibitior	-	0.4540	45.40%
P-glycoprotein substrate	-	0.5539	55.39%
CYP3A4 substrate	+	0.6161	61.61%
CYP2C9 substrate	-	0.6180	61.80%
CYP2D6 substrate	+	0.5879	58.79%
CYP3A4 inhibition	-	0.6891	68.91%
CYP2C9 inhibition	+	0.5650	56.50%
CYP2C19 inhibition	+	0.8178	81.78%
CYP2D6 inhibition	-	0.8128	81.28%
CYP1A2 inhibition	+	0.9482	94.82%
CYP2C8 inhibition	+	0.8769	87.69%
CYP inhibitory promiscuity	+	0.6401	64.01%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7332	73.32%
Carcinogenicity (trinary)	Non-required	0.5921	59.21%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.4826	48.26%
Skin irritation	-	0.6940	69.40%
Skin corrosion	-	0.9055	90.55%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7470	74.70%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8743	87.43%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7787	77.87%
Acute Oral Toxicity (c)	III	0.5891	58.91%
Estrogen receptor binding	+	0.9309	93.09%
Androgen receptor binding	+	0.8725	87.25%
Thyroid receptor binding	+	0.6913	69.13%
Glucocorticoid receptor binding	+	0.8074	80.74%
Aromatase binding	+	0.5651	56.51%
PPAR gamma	+	0.8778	87.78%
Honey bee toxicity	-	0.8599	85.99%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6751	67.51%
Fish aquatic toxicity	+	0.9856	98.56%

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	97.57%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.30%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	96.87%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.64%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.05%	91.49%
CHEMBL2535	P11166	Glucose transporter	93.18%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.03%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.30%	86.33%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.95%	91.79%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.25%	95.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.42%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.22%	94.45%
CHEMBL4208	P20618	Proteasome component C5	89.22%	90.00%
CHEMBL261	P00915	Carbonic anhydrase I	89.15%	96.76%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.29%	94.00%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	88.23%	97.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.85%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.71%	93.40%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.84%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.74%	95.78%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.98%	96.95%
CHEMBL5747	Q92793	CREB-binding protein	83.29%	95.12%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	80.76%	98.11%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.34%	85.00%
CHEMBL3194	P02766	Transthyretin	80.07%	90.71%

Plants that contains it

• Bletilla formosana
• Bletilla striata
• Gymnadenia conopsea
• Pleione bulbocodioides
• Syzygium aromaticum

Cross-Links

• PubChem: 11163864
• NPASS: NPC105620
• LOTUS: LTS0244432
• wikiData: Q105331873