(3aS,4aR,5R,9aR)-3a,5-dihydroxy-9a-methoxy-4a,5-dimethyl-3-methylidene-4H-benzo[][1]benzouran-6-one

Details

• Internal ID: 1826cc80-2762-42a7-95c3-06d753e8827c
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (3aS,4aR,5R,9aR)-3a,5-dihydroxy-9a-methoxy-4a,5-dimethyl-3-methylidene-4H-benzo[f][1]benzofuran-6-one
• SMILES (Canonical): CC12CC3(C(=C)COC3(C=C1C=CC(=O)C2(C)O)OC)O
• SMILES (Isomeric): C[C@@]12C[C@@]3(C(=C)CO[C@@]3(C=C1C=CC(=O)[C@]2(C)O)OC)O
• InChI: InChI=1S/C16H20O5/c1-10-8-21-16(20-4)7-11-5-6-12(17)14(3,18)13(11,2)9-15(10,16)19/h5-7,18-19H,1,8-9H2,2-4H3/t13-,14+,15+,16-/m1/s1
• InChI Key: LTQBFDFZNQYYQL-FXUDXRNXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.33 g/mol
• Exact Mass: 292.13107373 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.87
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• (3aS,4aR,5R,9aR)-3a,5-dihydroxy-9a-methoxy-4a,5-dimethyl-3-methylidene-4H-benzo[][1]benzouran-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.6863	68.63%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7269	72.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8518	85.18%
P-glycoprotein inhibitior	-	0.9357	93.57%
P-glycoprotein substrate	-	0.7478	74.78%
CYP3A4 substrate	+	0.5886	58.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8772	87.72%
CYP3A4 inhibition	-	0.6120	61.20%
CYP2C9 inhibition	-	0.8406	84.06%
CYP2C19 inhibition	-	0.8621	86.21%
CYP2D6 inhibition	-	0.9463	94.63%
CYP1A2 inhibition	-	0.7596	75.96%
CYP2C8 inhibition	-	0.8063	80.63%
CYP inhibitory promiscuity	-	0.8903	89.03%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5253	52.53%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.7955	79.55%
Skin irritation	-	0.5162	51.62%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6010	60.10%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6773	67.73%
skin sensitisation	-	0.8623	86.23%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5384	53.84%
Acute Oral Toxicity (c)	I	0.3582	35.82%
Estrogen receptor binding	+	0.6861	68.61%
Androgen receptor binding	+	0.7116	71.16%
Thyroid receptor binding	+	0.6332	63.32%
Glucocorticoid receptor binding	+	0.5412	54.12%
Aromatase binding	+	0.5567	55.67%
PPAR gamma	-	0.5427	54.27%
Honey bee toxicity	-	0.7883	78.83%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9920	99.20%

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	96.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.61%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.16%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.22%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.18%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.32%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.23%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.96%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.58%	97.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.10%	97.25%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139584840
• LOTUS: LTS0023954
• wikiData: Q77376808