3a-methoxy-1,5,8-trimethyl-5,5a,6,9a-tetrahydro-4H-benzo[e][1]benzofuran-2,7-dione

Details

• Internal ID: c10ae5f4-7900-4748-bc68-23bfcc672108
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 3a-methoxy-1,5,8-trimethyl-5,5a,6,9a-tetrahydro-4H-benzo[e][1]benzofuran-2,7-dione
• SMILES (Canonical): CC1CC2(C(=C(C(=O)O2)C)C3C1CC(=O)C(=C3)C)OC
• SMILES (Isomeric): CC1CC2(C(=C(C(=O)O2)C)C3C1CC(=O)C(=C3)C)OC
• InChI: InChI=1S/C16H20O4/c1-8-5-12-11(6-13(8)17)9(2)7-16(19-4)14(12)10(3)15(18)20-16/h5,9,11-12H,6-7H2,1-4H3
• InChI Key: BYYMEOQTMBNNEA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.33 g/mol
• Exact Mass: 276.13615911 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9931	99.31%
Caco-2	+	0.8415	84.15%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6257	62.57%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9093	90.93%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7415	74.15%
P-glycoprotein inhibitior	-	0.8894	88.94%
P-glycoprotein substrate	-	0.8024	80.24%
CYP3A4 substrate	+	0.5996	59.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8919	89.19%
CYP3A4 inhibition	+	0.5242	52.42%
CYP2C9 inhibition	-	0.8685	86.85%
CYP2C19 inhibition	-	0.8922	89.22%
CYP2D6 inhibition	-	0.9649	96.49%
CYP1A2 inhibition	-	0.6208	62.08%
CYP2C8 inhibition	-	0.6963	69.63%
CYP inhibitory promiscuity	-	0.7174	71.74%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4586	45.86%
Eye corrosion	-	0.9766	97.66%
Eye irritation	-	0.7338	73.38%
Skin irritation	-	0.6306	63.06%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4251	42.51%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6335	63.35%
skin sensitisation	-	0.7892	78.92%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.6413	64.13%
Acute Oral Toxicity (c)	III	0.5142	51.42%
Estrogen receptor binding	-	0.6503	65.03%
Androgen receptor binding	+	0.5533	55.33%
Thyroid receptor binding	-	0.6159	61.59%
Glucocorticoid receptor binding	-	0.5343	53.43%
Aromatase binding	-	0.8051	80.51%
PPAR gamma	-	0.5636	56.36%
Honey bee toxicity	-	0.7251	72.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9927	99.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.00%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.19%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.63%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.49%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	85.64%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.02%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.40%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.18%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.16%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.11%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.63%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	80.60%	94.73%

Plants that contains it

• Smallanthus uvedalia

Cross-Links

• PubChem: 14108878
• LOTUS: LTS0164007
• wikiData: Q104950171