(3aS,4S,9aS)-4-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-1,3,3a,4,9,9a-hexahydrobenzo[f][2]benzofuran-5,6-diol

Details

• Internal ID: c10f07cb-3f77-47fc-9d64-7d036c929178
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (3aS,4S,9aS)-4-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-1,3,3a,4,9,9a-hexahydrobenzo[f][2]benzofuran-5,6-diol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C3COCC3CC4=CC(=C(C(=C24)O)O)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@@H]2[C@@H]3COC[C@H]3CC4=CC(=C(C(=C24)O)O)OC
• InChI: InChI=1S/C21H24O7/c1-25-14-6-11(7-15(26-2)19(14)22)17-13-9-28-8-12(13)4-10-5-16(27-3)20(23)21(24)18(10)17/h5-7,12-13,17,22-24H,4,8-9H2,1-3H3/t12-,13-,17-/m1/s1
• InChI Key: MBBZRCCRPPDOEH-PBFPGSCMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.15220310 g/mol
• Topological Polar Surface Area (TPSA): 97.60 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9580	95.80%
Caco-2	+	0.5608	56.08%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7956	79.56%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.8459	84.59%
OATP1B3 inhibitior	+	0.9682	96.82%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6173	61.73%
P-glycoprotein substrate	-	0.6914	69.14%
CYP3A4 substrate	+	0.5551	55.51%
CYP2C9 substrate	-	0.6124	61.24%
CYP2D6 substrate	+	0.4880	48.80%
CYP3A4 inhibition	-	0.6276	62.76%
CYP2C9 inhibition	+	0.5805	58.05%
CYP2C19 inhibition	+	0.6333	63.33%
CYP2D6 inhibition	-	0.8625	86.25%
CYP1A2 inhibition	+	0.5194	51.94%
CYP2C8 inhibition	+	0.5251	52.51%
CYP inhibitory promiscuity	+	0.7126	71.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9008	90.08%
Carcinogenicity (trinary)	Non-required	0.5129	51.29%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.7249	72.49%
Skin irritation	-	0.8267	82.67%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.6195	61.95%
skin sensitisation	-	0.8358	83.58%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7455	74.55%
Acute Oral Toxicity (c)	III	0.5704	57.04%
Estrogen receptor binding	+	0.7958	79.58%
Androgen receptor binding	+	0.7339	73.39%
Thyroid receptor binding	+	0.7757	77.57%
Glucocorticoid receptor binding	+	0.8332	83.32%
Aromatase binding	-	0.5495	54.95%
PPAR gamma	+	0.6452	64.52%
Honey bee toxicity	-	0.6942	69.42%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9754	97.54%

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	98.08%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.24%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.96%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.70%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.66%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.18%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.15%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.99%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.70%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.26%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.86%	95.89%

Plants that contains it

• Pinalia yunnanensis

Cross-Links

• PubChem: 162937306
• LOTUS: LTS0199875
• wikiData: Q105160651