Kadsurenin L

Details

• Internal ID: 879a5583-117b-429a-9879-54c7268a08cb
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Methoxybenzenes > Dimethoxybenzenes
• IUPAC Name: [(1R,5S,6R,7R,8S)-6-(3,4-dimethoxyphenyl)-1-methoxy-7-methyl-4-oxo-3-prop-2-enyl-8-bicyclo[3.2.1]oct-2-enyl] acetate
• SMILES (Canonical): CC1C(C2C(C1(C=C(C2=O)CC=C)OC)OC(=O)C)C3=CC(=C(C=C3)OC)OC
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H]2[C@@H]([C@@]1(C=C(C2=O)CC=C)OC)OC(=O)C)C3=CC(=C(C=C3)OC)OC
• InChI: InChI=1S/C23H28O6/c1-7-8-16-12-23(28-6)13(2)19(20(21(16)25)22(23)29-14(3)24)15-9-10-17(26-4)18(11-15)27-5/h7,9-13,19-20,22H,1,8H2,2-6H3/t13-,19+,20-,22+,23+/m1/s1
• InChI Key: TVDQUJSTRADHSU-WWDCKHPPSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.18858861 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 149438-61-9
• delta(8')-3,4,5'-Trimethoxy-4'-acetoxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan
• [(1R,5S,6R,7R,8S)-6-(3,4-dimethoxyphenyl)-1-methoxy-7-methyl-4-oxo-3-prop-2-enyl-8-bicyclo[3.2.1]oct-2-enyl] acetate
• Bicyclo(3.2.1)oct-3-en-2-one, 8-(acetyloxy)-7-(3,4-dimethoxyphenyl)-5-methoxy-6-methyl-3-(2-propenyl)-, (1S-(6-endo,7-exo,8-syn))-
• CHEMBL594049
• DTXSID60933648
• CHEBI:132653
• (1R,5S,6R,7R,8S)-6-(3,4-dimethoxyphenyl)-1-methoxy-7-methyl-4-oxo-3-(prop-2-en-1-yl)bicyclo[3.2.1]oct-2-en-8-yl acetate
• (1S,5R,6R,7R,8S)-3-Allyl-5-methoxy-6-methyl-7-(3,4-dimethoxyphenyl)-8-acetoxybicyclo[3.2.1]octa-3-ene-2-one
• 6-(3,4-Dimethoxyphenyl)-1-methoxy-7-methyl-4-oxo-3-(prop-2-en-1-yl)bicyclo[3.2.1]oct-2-en-8-yl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.7029	70.29%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7802	78.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.8972	89.72%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8271	82.71%
P-glycoprotein inhibitior	+	0.8462	84.62%
P-glycoprotein substrate	-	0.6009	60.09%
CYP3A4 substrate	+	0.6060	60.60%
CYP2C9 substrate	-	0.7769	77.69%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	+	0.6782	67.82%
CYP2C9 inhibition	-	0.6401	64.01%
CYP2C19 inhibition	+	0.6494	64.94%
CYP2D6 inhibition	-	0.9324	93.24%
CYP1A2 inhibition	-	0.6879	68.79%
CYP2C8 inhibition	+	0.4566	45.66%
CYP inhibitory promiscuity	+	0.6384	63.84%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8296	82.96%
Carcinogenicity (trinary)	Non-required	0.5157	51.57%
Eye corrosion	-	0.9810	98.10%
Eye irritation	-	0.8575	85.75%
Skin irritation	-	0.7718	77.18%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7557	75.57%
Micronuclear	+	0.5992	59.92%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.7513	75.13%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.6483	64.83%
Acute Oral Toxicity (c)	III	0.4972	49.72%
Estrogen receptor binding	+	0.8688	86.88%
Androgen receptor binding	+	0.6751	67.51%
Thyroid receptor binding	+	0.6578	65.78%
Glucocorticoid receptor binding	+	0.8185	81.85%
Aromatase binding	+	0.5896	58.96%
PPAR gamma	+	0.5396	53.96%
Honey bee toxicity	-	0.7786	77.86%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6652	66.52%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.06%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.98%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.11%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.19%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.73%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.30%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.04%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.33%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.80%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.53%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.52%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.38%	91.07%
CHEMBL4530	P00488	Coagulation factor XIII	82.14%	96.00%
CHEMBL4208	P20618	Proteasome component C5	82.06%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.26%	95.89%
CHEMBL2535	P11166	Glucose transporter	80.47%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.34%	95.89%

Plants that contains it

• Castilleja sulphurea
• Dioscorea villosa
• Forsythia japonica
• Gymnosporia pyria
• Huperzia miyoshiana
• Lindera aggregata
• Piper kadsura
• Pseudobrickellia brasiliensis
• Rhododendron latoucheae

Cross-Links

• PubChem: 3083437
• NPASS: NPC139209
• LOTUS: LTS0269905
• wikiData: Q82909480