[(4S,4aR,5S,7R)-7-hydroxy-4a,5-dimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: e263a39d-757e-494e-b910-4ec151a0bddb
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(4S,4aR,5S,7R)-7-hydroxy-4a,5-dimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(C(=O)C3=CC(CC(C13C)C)O)OC=C2
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C(C(=O)C3=C[C@@H](C[C@@H]([C@@]13C)C)O)OC=C2
• InChI: InChI=1S/C19H22O5/c1-5-10(2)18(22)24-17-13-6-7-23-16(13)15(21)14-9-12(20)8-11(3)19(14,17)4/h5-7,9,11-12,17,20H,8H2,1-4H3/b10-5-/t11-,12+,17+,19+/m0/s1
• InChI Key: VWUPQZXUHCYORA-ZEQRYJAYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.6842	68.42%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6578	65.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8739	87.39%
OATP1B3 inhibitior	+	0.8814	88.14%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5824	58.24%
P-glycoprotein inhibitior	-	0.6688	66.88%
P-glycoprotein substrate	-	0.6257	62.57%
CYP3A4 substrate	+	0.6626	66.26%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.7002	70.02%
CYP2C9 inhibition	-	0.7584	75.84%
CYP2C19 inhibition	-	0.8182	81.82%
CYP2D6 inhibition	-	0.8608	86.08%
CYP1A2 inhibition	-	0.5316	53.16%
CYP2C8 inhibition	-	0.6054	60.54%
CYP inhibitory promiscuity	-	0.7412	74.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4098	40.98%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9550	95.50%
Skin irritation	-	0.5963	59.63%
Skin corrosion	-	0.9342	93.42%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7525	75.25%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.5827	58.27%
skin sensitisation	-	0.7222	72.22%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4936	49.36%
Acute Oral Toxicity (c)	III	0.3722	37.22%
Estrogen receptor binding	+	0.5416	54.16%
Androgen receptor binding	+	0.5974	59.74%
Thyroid receptor binding	-	0.6396	63.96%
Glucocorticoid receptor binding	-	0.5262	52.62%
Aromatase binding	+	0.5620	56.20%
PPAR gamma	+	0.6120	61.20%
Honey bee toxicity	-	0.5998	59.98%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9922	99.22%

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	98.17%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.75%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.25%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.18%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.03%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.55%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.50%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.96%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.83%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.00%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.25%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.40%	92.94%

Plants that contains it

• Packera bellidifolia

Cross-Links

• PubChem: 162820138
• LOTUS: LTS0102223
• wikiData: Q103813534