(7R,8S,9R)-9-(1,3-benzodioxol-5-yl)-4-methoxy-7,8-dimethyl-7,8-dihydro-6H-benzo[g][1,3]benzodioxol-9-ol

Details

• Internal ID: 577f4ae0-7ad9-4b14-9f00-38fa51adf356
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (7R,8S,9R)-9-(1,3-benzodioxol-5-yl)-4-methoxy-7,8-dimethyl-7,8-dihydro-6H-benzo[g][1,3]benzodioxol-9-ol
• SMILES (Canonical): CC1CC2=CC(=C3C(=C2C(C1C)(C4=CC5=C(C=C4)OCO5)O)OCO3)OC
• SMILES (Isomeric): C[C@@H]1CC2=CC(=C3C(=C2[C@@]([C@H]1C)(C4=CC5=C(C=C4)OCO5)O)OCO3)OC
• InChI: InChI=1S/C21H22O6/c1-11-6-13-7-17(23-3)19-20(27-10-26-19)18(13)21(22,12(11)2)14-4-5-15-16(8-14)25-9-24-15/h4-5,7-8,11-12,22H,6,9-10H2,1-3H3/t11-,12+,21-/m1/s1
• InChI Key: KCYVBPCJWBVYJQ-SMDDFHAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14163842 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9678	96.78%
Caco-2	+	0.8503	85.03%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6029	60.29%
OATP2B1 inhibitior	-	0.8665	86.65%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7751	77.51%
P-glycoprotein inhibitior	+	0.5967	59.67%
P-glycoprotein substrate	-	0.6282	62.82%
CYP3A4 substrate	+	0.5856	58.56%
CYP2C9 substrate	-	0.5852	58.52%
CYP2D6 substrate	+	0.3508	35.08%
CYP3A4 inhibition	+	0.6942	69.42%
CYP2C9 inhibition	+	0.7250	72.50%
CYP2C19 inhibition	+	0.6479	64.79%
CYP2D6 inhibition	-	0.7583	75.83%
CYP1A2 inhibition	-	0.8313	83.13%
CYP2C8 inhibition	-	0.6890	68.90%
CYP inhibitory promiscuity	+	0.7307	73.07%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9408	94.08%
Carcinogenicity (trinary)	Non-required	0.3800	38.00%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8482	84.82%
Skin irritation	-	0.7973	79.73%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6817	68.17%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5301	53.01%
skin sensitisation	-	0.8322	83.22%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6354	63.54%
Acute Oral Toxicity (c)	III	0.4840	48.40%
Estrogen receptor binding	+	0.8155	81.55%
Androgen receptor binding	+	0.6962	69.62%
Thyroid receptor binding	+	0.7340	73.40%
Glucocorticoid receptor binding	+	0.8458	84.58%
Aromatase binding	+	0.6465	64.65%
PPAR gamma	+	0.8470	84.70%
Honey bee toxicity	-	0.7889	78.89%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6451	64.51%
Fish aquatic toxicity	+	0.9816	98.16%

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	96.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.36%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.64%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.85%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.42%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.21%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.98%	90.24%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.78%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.45%	92.62%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.21%	86.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.84%	82.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.71%	95.56%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.19%	94.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.83%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.66%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.11%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.68%	97.09%
CHEMBL2535	P11166	Glucose transporter	82.60%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.17%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.06%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.08%	85.14%
CHEMBL4208	P20618	Proteasome component C5	81.06%	90.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.21%	85.30%

Plants that contains it

• Virola calophylloidea

Cross-Links

• PubChem: 163185674
• LOTUS: LTS0031430
• wikiData: Q105139029