(2R,6aS,12aS)-1,2,6,6a,12,12a-Hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b] furo(2,3-h)chromen-6-one

Details

• Internal ID: 820d30b3-04dc-4ac5-8366-2b9729338f9e
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 8-prenylated isoflavanones
• IUPAC Name: (1R,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7-dioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• SMILES (Canonical): CC(=C)C1CC2=C(O1)C=CC3=C2OC4CCC5=CC(=C(C=C5C4C3=O)OC)OC
• SMILES (Isomeric): CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4CCC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC
• InChI: InChI=1S/C24H24O5/c1-12(2)19-11-16-17(28-19)8-6-14-23(25)22-15-10-21(27-4)20(26-3)9-13(15)5-7-18(22)29-24(14)16/h6,8-10,18-19,22H,1,5,7,11H2,2-4H3/t18-,19-,22+/m1/s1
• InChI Key: MGMLAUOOTBJKRK-KNKQGSTJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₅
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.16237386 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.26
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	+	0.6698	66.98%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6960	69.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4070	40.70%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8547	85.47%
P-glycoprotein inhibitior	+	0.8921	89.21%
P-glycoprotein substrate	+	0.5096	50.96%
CYP3A4 substrate	+	0.6710	67.10%
CYP2C9 substrate	-	0.7859	78.59%
CYP2D6 substrate	-	0.7307	73.07%
CYP3A4 inhibition	+	0.6539	65.39%
CYP2C9 inhibition	-	0.8545	85.45%
CYP2C19 inhibition	+	0.7948	79.48%
CYP2D6 inhibition	-	0.8540	85.40%
CYP1A2 inhibition	+	0.8855	88.55%
CYP2C8 inhibition	+	0.5586	55.86%
CYP inhibitory promiscuity	+	0.7759	77.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5789	57.89%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.5725	57.25%
Skin irritation	-	0.7495	74.95%
Skin corrosion	-	0.9494	94.94%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6691	66.91%
Micronuclear	-	0.6241	62.41%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6940	69.40%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.6647	66.47%
Acute Oral Toxicity (c)	II	0.5500	55.00%
Estrogen receptor binding	+	0.8871	88.71%
Androgen receptor binding	+	0.6479	64.79%
Thyroid receptor binding	+	0.8157	81.57%
Glucocorticoid receptor binding	+	0.8556	85.56%
Aromatase binding	-	0.5937	59.37%
PPAR gamma	+	0.8532	85.32%
Honey bee toxicity	+	0.7756	77.56%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.9748	97.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.02%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.86%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.45%	92.94%
CHEMBL2581	P07339	Cathepsin D	94.81%	98.95%
CHEMBL217	P14416	Dopamine D2 receptor	93.51%	95.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.06%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.91%	95.89%
CHEMBL2535	P11166	Glucose transporter	90.50%	98.75%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.27%	95.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.32%	95.89%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	87.96%	96.86%
CHEMBL1951	P21397	Monoamine oxidase A	87.68%	91.49%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.37%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.25%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.17%	86.33%
CHEMBL2056	P21728	Dopamine D1 receptor	85.56%	91.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.33%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.22%	99.17%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.20%	97.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.96%	93.40%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.57%	89.50%
CHEMBL1902	P62942	FK506-binding protein 1A	81.74%	97.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.82%	92.62%

Plants that contains it

• Neorautanenia mitis

Cross-Links

• PubChem: 24794374
• LOTUS: LTS0037052
• wikiData: Q105163440