1,8-Bis[(4-hydroxyphenyl)methyl]-7-methoxy-3-phenyl-9,10-dihydrophenanthrene-2,4,5-triol

Details

• Internal ID: 8c74252f-4292-4bc9-bdc0-de6739172be3
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 1,8-bis[(4-hydroxyphenyl)methyl]-7-methoxy-3-phenyl-9,10-dihydrophenanthrene-2,4,5-triol
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)C3=C(C(=C(C(=C3CC2)CC4=CC=C(C=C4)O)O)C5=CC=CC=C5)O)CC6=CC=C(C=C6)O
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)C3=C(C(=C(C(=C3CC2)CC4=CC=C(C=C4)O)O)C5=CC=CC=C5)O)CC6=CC=C(C=C6)O
• InChI: InChI=1S/C35H30O6/c1-41-30-19-29(38)32-25(27(30)17-20-7-11-23(36)12-8-20)15-16-26-28(18-21-9-13-24(37)14-10-21)34(39)31(35(40)33(26)32)22-5-3-2-4-6-22/h2-14,19,36-40H,15-18H2,1H3
• InChI Key: AYCMOFRTAVBQIM-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₃₀O₆
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.20423867 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 7.50
• Atomic LogP (AlogP): 6.84
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 1,8-bis[(4-hydroxyphenyl)methyl]-7-methoxy-3-phenyl-9,10-dihydrophenanthrene-2,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9671	96.71%
Caco-2	-	0.7991	79.91%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8832	88.32%
OATP2B1 inhibitior	-	0.5662	56.62%
OATP1B1 inhibitior	+	0.8015	80.15%
OATP1B3 inhibitior	+	0.9155	91.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9799	97.99%
P-glycoprotein inhibitior	+	0.9004	90.04%
P-glycoprotein substrate	-	0.7185	71.85%
CYP3A4 substrate	+	0.5782	57.82%
CYP2C9 substrate	-	0.6180	61.80%
CYP2D6 substrate	+	0.5879	58.79%
CYP3A4 inhibition	-	0.6084	60.84%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.6530	65.30%
CYP2D6 inhibition	-	0.8273	82.73%
CYP1A2 inhibition	+	0.8511	85.11%
CYP2C8 inhibition	+	0.9363	93.63%
CYP inhibitory promiscuity	+	0.7907	79.07%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7811	78.11%
Carcinogenicity (trinary)	Non-required	0.6227	62.27%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.7699	76.99%
Skin irritation	-	0.7040	70.40%
Skin corrosion	-	0.8816	88.16%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9540	95.40%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5051	50.51%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8334	83.34%
Acute Oral Toxicity (c)	III	0.5732	57.32%
Estrogen receptor binding	+	0.8956	89.56%
Androgen receptor binding	+	0.8739	87.39%
Thyroid receptor binding	+	0.5846	58.46%
Glucocorticoid receptor binding	+	0.8094	80.94%
Aromatase binding	+	0.6094	60.94%
PPAR gamma	+	0.7344	73.44%
Honey bee toxicity	-	0.8518	85.18%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5851	58.51%
Fish aquatic toxicity	+	0.9877	98.77%

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	98.19%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.45%	98.95%
CHEMBL240	Q12809	HERG	96.09%	89.76%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	95.76%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.73%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.70%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.44%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.88%	95.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.53%	91.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.16%	93.99%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.41%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.50%	94.00%
CHEMBL4208	P20618	Proteasome component C5	86.66%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.96%	99.15%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.93%	91.79%
CHEMBL2535	P11166	Glucose transporter	85.55%	98.75%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.44%	92.67%
CHEMBL1255126	O15151	Protein Mdm4	84.43%	90.20%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	84.31%	98.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.99%	95.89%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.29%	94.03%

Plants that contains it

• Spiranthes vernalis

Cross-Links

• PubChem: 11006106
• LOTUS: LTS0045156
• wikiData: Q104920973