[(3R,4S,4aS,5R,6S,8aR)-4-hydroxy-3,4a,5-trimethyl-2-oxo-3,4,5,6,7,8,8a,9-octahydrobenzo[f][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 5d58137c-d802-458a-b094-db173aefc37f
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(3R,4S,4aS,5R,6S,8aR)-4-hydroxy-3,4a,5-trimethyl-2-oxo-3,4,5,6,7,8,8a,9-octahydrobenzo[f][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2CC3=C(C(C(=O)O3)C)C(C2(C1C)C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC[C@@H]2CC3=C([C@H](C(=O)O3)C)[C@H]([C@@]2([C@H]1C)C)O
• InChI: InChI=1S/C20H28O5/c1-6-10(2)18(22)24-14-8-7-13-9-15-16(11(3)19(23)25-15)17(21)20(13,5)12(14)4/h6,11-14,17,21H,7-9H2,1-5H3/b10-6-/t11-,12+,13-,14+,17-,20-/m1/s1
• InChI Key: UWCGEWFAZBWFAD-QHXMAMPQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.13
• 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	+	0.9858	98.58%
Caco-2	+	0.6760	67.60%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7933	79.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8853	88.53%
OATP1B3 inhibitior	+	0.8944	89.44%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	-	0.4634	46.34%
P-glycoprotein inhibitior	-	0.6109	61.09%
P-glycoprotein substrate	-	0.6177	61.77%
CYP3A4 substrate	+	0.6461	64.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9000	90.00%
CYP3A4 inhibition	-	0.6487	64.87%
CYP2C9 inhibition	-	0.8503	85.03%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	+	0.7045	70.45%
CYP2C8 inhibition	-	0.7844	78.44%
CYP inhibitory promiscuity	-	0.8147	81.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4375	43.75%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9608	96.08%
Skin irritation	+	0.5998	59.98%
Skin corrosion	-	0.8471	84.71%
Ames mutagenesis	-	0.6118	61.18%
Human Ether-a-go-go-Related Gene inhibition	+	0.6671	66.71%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7033	70.33%
skin sensitisation	-	0.8121	81.21%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7067	70.67%
Acute Oral Toxicity (c)	III	0.5592	55.92%
Estrogen receptor binding	+	0.8801	88.01%
Androgen receptor binding	+	0.5275	52.75%
Thyroid receptor binding	+	0.6913	69.13%
Glucocorticoid receptor binding	+	0.7837	78.37%
Aromatase binding	-	0.5846	58.46%
PPAR gamma	+	0.6317	63.17%
Honey bee toxicity	-	0.6797	67.97%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9836	98.36%

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	96.36%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.57%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.37%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.13%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.24%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.41%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.18%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.19%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.88%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.81%	100.00%

Plants that contains it

• Dioscorea alata
• Farfugium japonicum

Cross-Links

• PubChem: 162907110
• LOTUS: LTS0268772
• wikiData: Q105147396