(2R,3R,4S,5S,6R)-2-[(7-hydroxy-2-methoxy-1,8-dimethyl-9,10-dihydrophenanthren-4-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 82f1f052-7449-4c2b-acbf-15600608541c
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(7-hydroxy-2-methoxy-1,8-dimethyl-9,10-dihydrophenanthren-4-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1=C(C=CC2=C1CCC3=C2C(=CC(=C3C)OC)COC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): CC1=C(C=CC2=C1CCC3=C2C(=CC(=C3C)OC)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C24H30O8/c1-11-14-4-5-15-12(2)18(30-3)8-13(20(15)16(14)6-7-17(11)26)10-31-24-23(29)22(28)21(27)19(9-25)32-24/h6-8,19,21-29H,4-5,9-10H2,1-3H3/t19-,21-,22+,23-,24-/m1/s1
• InChI Key: WTQDTXUORVBHFF-PFKOEMKTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.50 g/mol
• Exact Mass: 446.19406791 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5619	56.19%
Caco-2	-	0.7154	71.54%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6415	64.15%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8434	84.34%
OATP1B3 inhibitior	+	0.9328	93.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7472	74.72%
P-glycoprotein inhibitior	-	0.6599	65.99%
P-glycoprotein substrate	-	0.6895	68.95%
CYP3A4 substrate	+	0.6251	62.51%
CYP2C9 substrate	-	0.8022	80.22%
CYP2D6 substrate	-	0.7622	76.22%
CYP3A4 inhibition	-	0.9660	96.60%
CYP2C9 inhibition	-	0.8778	87.78%
CYP2C19 inhibition	-	0.8152	81.52%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.6491	64.91%
CYP2C8 inhibition	+	0.6738	67.38%
CYP inhibitory promiscuity	-	0.8770	87.70%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7424	74.24%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9414	94.14%
Skin irritation	-	0.8273	82.73%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4187	41.87%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7249	72.49%
skin sensitisation	-	0.9077	90.77%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6305	63.05%
Acute Oral Toxicity (c)	III	0.6449	64.49%
Estrogen receptor binding	+	0.7704	77.04%
Androgen receptor binding	+	0.6431	64.31%
Thyroid receptor binding	+	0.5979	59.79%
Glucocorticoid receptor binding	+	0.6477	64.77%
Aromatase binding	+	0.5607	56.07%
PPAR gamma	+	0.6953	69.53%
Honey bee toxicity	-	0.8286	82.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.7986	79.86%

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	99.37%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.01%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.95%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.94%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.04%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	90.49%	98.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.37%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.00%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.19%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.15%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.10%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	87.94%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.44%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.16%	91.49%
CHEMBL4208	P20618	Proteasome component C5	87.08%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.78%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.53%	95.89%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	86.33%	91.79%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.09%	92.94%
CHEMBL2535	P11166	Glucose transporter	83.08%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.88%	92.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.01%	97.36%
CHEMBL3194	P02766	Transthyretin	80.62%	90.71%

Plants that contains it

• Juncus effusus

Cross-Links

• PubChem: 92024077
• LOTUS: LTS0266327
• wikiData: Q105312710