5-Allyl-3,8-dihydroxy-1-methoxy-7-(7-methoxy-1,3-benzodioxol-5-yl)-6-methylbicyclo[3.2.1]oct-3-en-2-one

Details

• Internal ID: d9025e03-e0df-4454-9d53-bda0b4ca3c36
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: 3,8-dihydroxy-1-methoxy-7-(7-methoxy-1,3-benzodioxol-5-yl)-6-methyl-5-prop-2-enylbicyclo[3.2.1]oct-3-en-2-one
• SMILES (Canonical): CC1C(C2(C(C1(C=C(C2=O)O)CC=C)O)OC)C3=CC4=C(C(=C3)OC)OCO4
• SMILES (Isomeric): CC1C(C2(C(C1(C=C(C2=O)O)CC=C)O)OC)C3=CC4=C(C(=C3)OC)OCO4
• InChI: InChI=1S/C21H24O7/c1-5-6-20-9-13(22)18(23)21(26-4,19(20)24)16(11(20)2)12-7-14(25-3)17-15(8-12)27-10-28-17/h5,7-9,11,16,19,22,24H,1,6,10H2,2-4H3
• InChI Key: DVNOGPNETZYAGV-UHFFFAOYSA-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): 94.50 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.49
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 5-Allyl-3,8-dihydroxy-1-methoxy-7-(7-methoxy-1,3-benzodioxol-5-yl)-6-methylbicyclo[3.2.1]oct-3-en-2-one #
• Bicyclo[3.2.1]oct-3-en-2-one, 3,8-dihydroxy-1-methoxy-7-(7-methoxy-1,3-benzodioxol-5-yl)-6-methyl-5-(2-propenyl)-, [1R-(6-endo,7-exo,8-syn)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	-	0.6228	62.28%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6873	68.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8849	88.49%
OATP1B3 inhibitior	+	0.8298	82.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4819	48.19%
P-glycoprotein inhibitior	-	0.6042	60.42%
P-glycoprotein substrate	-	0.6063	60.63%
CYP3A4 substrate	+	0.6401	64.01%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8277	82.77%
CYP3A4 inhibition	+	0.7409	74.09%
CYP2C9 inhibition	+	0.5817	58.17%
CYP2C19 inhibition	+	0.6823	68.23%
CYP2D6 inhibition	-	0.8428	84.28%
CYP1A2 inhibition	-	0.7751	77.51%
CYP2C8 inhibition	-	0.5740	57.40%
CYP inhibitory promiscuity	+	0.8115	81.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5637	56.37%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.7324	73.24%
Skin corrosion	-	0.9289	92.89%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4900	49.00%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.7801	78.01%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6234	62.34%
Acute Oral Toxicity (c)	III	0.4244	42.44%
Estrogen receptor binding	+	0.7456	74.56%
Androgen receptor binding	+	0.6824	68.24%
Thyroid receptor binding	+	0.7039	70.39%
Glucocorticoid receptor binding	+	0.7630	76.30%
Aromatase binding	+	0.5351	53.51%
PPAR gamma	+	0.7680	76.80%
Honey bee toxicity	-	0.6354	63.54%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9947	99.47%

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	99.46%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.31%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.87%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.18%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.37%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.26%	96.77%
CHEMBL2581	P07339	Cathepsin D	91.86%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.18%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.10%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.40%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.01%	86.33%
CHEMBL4208	P20618	Proteasome component C5	86.77%	90.00%
CHEMBL4530	P00488	Coagulation factor XIII	86.48%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.79%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.97%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.66%	96.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.07%	89.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.82%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.70%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	81.23%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.51%	95.89%

Plants that contains it

• Glottiphyllum longum
• Ocotea porosa

Cross-Links

• PubChem: 535324
• LOTUS: LTS0244459
• wikiData: Q27106439