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

Details

• Internal ID: 896741a8-57e1-45de-89d8-7329c9b7a396
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: 8-[(4-hydroxyphenyl)methyl]-7-methoxy-9,10-dihydrophenanthrene-2,5-diol
• SMILES (Canonical): COC1=C(C2=C(C3=C(CC2)C=C(C=C3)O)C(=C1)O)CC4=CC=C(C=C4)O
• SMILES (Isomeric): COC1=C(C2=C(C3=C(CC2)C=C(C=C3)O)C(=C1)O)CC4=CC=C(C=C4)O
• InChI: InChI=1S/C22H20O4/c1-26-21-12-20(25)22-17-9-7-16(24)11-14(17)4-8-18(22)19(21)10-13-2-5-15(23)6-3-13/h2-3,5-7,9,11-12,23-25H,4,8,10H2,1H3
• InChI Key: MXOFIBMBNJWOFF-UHFFFAOYSA-N
• Popularity: 9 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

• BDBM50160799
• 1-(4-Hydroxybenzyl)-2-methoxy-9,10-dihydrophenanthrene-4,7-diol
• 8-(4-Hydroxy-benzyl)-7-methoxy-9,10-dihydro-phenanthrene-2,5-diol
• 4,7-dihydroxy-1-(4-hydroxybenzyl)-2-methoxy-9,10-dihydrophenanthrene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9747	97.47%
Caco-2	-	0.5850	58.50%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8767	87.67%
OATP2B1 inhibitior	-	0.5693	56.93%
OATP1B1 inhibitior	+	0.7872	78.72%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9357	93.57%
P-glycoprotein inhibitior	-	0.5573	55.73%
P-glycoprotein substrate	-	0.6225	62.25%
CYP3A4 substrate	+	0.6215	62.15%
CYP2C9 substrate	-	0.6180	61.80%
CYP2D6 substrate	+	0.5879	58.79%
CYP3A4 inhibition	-	0.6421	64.21%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.7067	70.67%
CYP2D6 inhibition	-	0.8364	83.64%
CYP1A2 inhibition	+	0.8965	89.65%
CYP2C8 inhibition	+	0.8799	87.99%
CYP inhibitory promiscuity	+	0.7604	76.04%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7332	73.32%
Carcinogenicity (trinary)	Non-required	0.5787	57.87%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.6190	61.90%
Skin irritation	-	0.6621	66.21%
Skin corrosion	-	0.8974	89.74%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7912	79.12%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7782	77.82%
Acute Oral Toxicity (c)	III	0.5866	58.66%
Estrogen receptor binding	+	0.9521	95.21%
Androgen receptor binding	+	0.8552	85.52%
Thyroid receptor binding	+	0.6577	65.77%
Glucocorticoid receptor binding	+	0.8301	83.01%
Aromatase binding	+	0.7162	71.62%
PPAR gamma	+	0.8488	84.88%
Honey bee toxicity	-	0.8478	84.78%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6951	69.51%
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	97.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.38%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.04%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	94.88%	98.35%
CHEMBL1951	P21397	Monoamine oxidase A	94.83%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.47%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.44%	95.17%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	92.11%	91.79%
CHEMBL2535	P11166	Glucose transporter	91.32%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.10%	86.33%
CHEMBL4208	P20618	Proteasome component C5	90.15%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.75%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.87%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.53%	94.00%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	87.52%	97.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.60%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.50%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.19%	93.99%
CHEMBL3194	P02766	Transthyretin	84.70%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.29%	96.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.35%	93.40%
CHEMBL5747	Q92793	CREB-binding protein	81.30%	95.12%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.14%	95.50%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.88%	95.78%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.46%	85.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.39%	95.53%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.28%	89.62%

Plants that contains it

• Bletilla striata
• Pleione bulbocodioides
• Spiranthes vernalis
• Syzygium aromaticum

Cross-Links

• PubChem: 44392570
• NPASS: NPC282508
• LOTUS: LTS0089163
• wikiData: Q105174412