(5R)-5,6,7,8-Tetrahydro-5beta-(3,4,5-trimethoxyphenyl)-7alpha-(hydroxymethyl)naphtho[2,3-d]-1,3-dioxole-6beta-carboxylic acid methyl ester

Details

• Internal ID: 55e339e5-7d2c-4501-bdce-3c4ab6af076e
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: methyl (5R,6R,7R)-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2C(C(CC3=CC4=C(C=C23)OCO4)CO)C(=O)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]([C@@H](CC3=CC4=C(C=C23)OCO4)CO)C(=O)OC
• InChI: InChI=1S/C23H26O8/c1-26-18-7-13(8-19(27-2)22(18)28-3)20-15-9-17-16(30-11-31-17)6-12(15)5-14(10-24)21(20)23(25)29-4/h6-9,14,20-21,24H,5,10-11H2,1-4H3/t14-,20+,21-/m0/s1
• InChI Key: MXGHOMGUPJFHLU-DLPLYFIVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₈
• Molecular Weight: 430.40 g/mol
• Exact Mass: 430.16276778 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.53
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9817	98.17%
Caco-2	+	0.7839	78.39%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7417	74.17%
OATP2B1 inhibitior	-	0.8684	86.84%
OATP1B1 inhibitior	+	0.8885	88.85%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9248	92.48%
P-glycoprotein inhibitior	+	0.6646	66.46%
P-glycoprotein substrate	-	0.8010	80.10%
CYP3A4 substrate	+	0.5950	59.50%
CYP2C9 substrate	-	0.6095	60.95%
CYP2D6 substrate	-	0.7740	77.40%
CYP3A4 inhibition	+	0.7519	75.19%
CYP2C9 inhibition	+	0.8292	82.92%
CYP2C19 inhibition	+	0.8292	82.92%
CYP2D6 inhibition	-	0.9161	91.61%
CYP1A2 inhibition	-	0.8741	87.41%
CYP2C8 inhibition	+	0.4511	45.11%
CYP inhibitory promiscuity	+	0.8110	81.10%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4832	48.32%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9440	94.40%
Skin irritation	-	0.8126	81.26%
Skin corrosion	-	0.9668	96.68%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3707	37.07%
Micronuclear	+	0.8074	80.74%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.7891	78.91%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6394	63.94%
Acute Oral Toxicity (c)	III	0.5995	59.95%
Estrogen receptor binding	+	0.9099	90.99%
Androgen receptor binding	+	0.6542	65.42%
Thyroid receptor binding	+	0.7920	79.20%
Glucocorticoid receptor binding	+	0.8648	86.48%
Aromatase binding	-	0.6662	66.62%
PPAR gamma	+	0.6568	65.68%
Honey bee toxicity	-	0.7938	79.38%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9228	92.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.42%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.20%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.90%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	96.22%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.24%	99.17%
CHEMBL261	P00915	Carbonic anhydrase I	93.65%	96.76%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.38%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.55%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.86%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.33%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.81%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.40%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.52%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.80%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.38%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.57%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.55%	94.80%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.93%	89.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.51%	96.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.49%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.11%	90.71%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Plectranthus amboinicus
• Plumbago europaea
• Reissantia indica
• Rhodanthe stricta
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis

Cross-Links

• PubChem: 101618918
• NPASS: NPC191436
• LOTUS: LTS0119333
• wikiData: Q105174080