(7aR)-6-allyl-7a-(3-methylbut-2-enyl)-1,3-benzodioxol-5-one

Details

• Internal ID: e35093a0-fc37-4e98-a637-2c90295bd156
• Taxonomy: Organoheterocyclic compounds > Dioxolanes > 1,3-dioxolanes
• IUPAC Name: (7aR)-7a-(3-methylbut-2-enyl)-6-prop-2-enyl-1,3-benzodioxol-5-one
• SMILES (Canonical): CC(=CCC12C=C(C(=O)C=C1OCO2)CC=C)C
• SMILES (Isomeric): CC(=CC[C@@]12C=C(C(=O)C=C1OCO2)CC=C)C
• InChI: InChI=1S/C15H18O3/c1-4-5-12-9-15(7-6-11(2)3)14(8-13(12)16)17-10-18-15/h4,6,8-9H,1,5,7,10H2,2-3H3/t15-/m1/s1
• InChI Key: TYDFLFGNHKORKL-OAHLLOKOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.05
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• (?)-Illicinone A
• (7aR)-6-allyl-7a-(3-methylbut-2-enyl)-1,3-benzodioxol-5-one
• 1,3-Benzodioxol-5(7aH)-one, 7a-(3-methyl-2-butenyl)-6-(2-propenyl)-, (7aR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.6963	69.63%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7956	79.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9108	91.08%
OATP1B3 inhibitior	+	0.9344	93.44%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5571	55.71%
P-glycoprotein inhibitior	-	0.9226	92.26%
P-glycoprotein substrate	-	0.8459	84.59%
CYP3A4 substrate	+	0.5134	51.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8577	85.77%
CYP3A4 inhibition	-	0.6664	66.64%
CYP2C9 inhibition	-	0.8802	88.02%
CYP2C19 inhibition	-	0.7827	78.27%
CYP2D6 inhibition	-	0.8864	88.64%
CYP1A2 inhibition	-	0.6861	68.61%
CYP2C8 inhibition	-	0.8990	89.90%
CYP inhibitory promiscuity	-	0.6816	68.16%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5625	56.25%
Eye corrosion	-	0.9641	96.41%
Eye irritation	+	0.7463	74.63%
Skin irritation	-	0.6564	65.64%
Skin corrosion	-	0.9073	90.73%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6197	61.97%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6606	66.06%
skin sensitisation	+	0.4798	47.98%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.8866	88.66%
Acute Oral Toxicity (c)	III	0.5308	53.08%
Estrogen receptor binding	+	0.7774	77.74%
Androgen receptor binding	-	0.5076	50.76%
Thyroid receptor binding	-	0.5161	51.61%
Glucocorticoid receptor binding	-	0.6264	62.64%
Aromatase binding	+	0.6343	63.43%
PPAR gamma	-	0.4877	48.77%
Honey bee toxicity	-	0.8043	80.43%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9880	98.80%

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	97.47%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.50%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.68%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.55%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.15%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.71%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.13%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.17%	100.00%

Plants that contains it

• Albizia julibrissin
• Anacardium occidentale
• Anchusa officinalis
• Caryopteris mongholica
• Dalbergia rubiginosa
• Euphorbia kansui
• Illicium verum
• Mappia nimmoniana
• Mesembryanthemum tortuosum
• Satureja atropatana

Cross-Links

• PubChem: 16721104
• NPASS: NPC232881
• LOTUS: LTS0176685
• wikiData: Q105267265