(4S,4aR,5R,8aS)-5-hydroxy-4a,8,8-trimethylspiro[1,3,5,6,7,8a-hexahydronaphthalene-4,5'-furan]-2,2'-dione

Details

• Internal ID: e7560c5b-617f-434b-abf1-1abadad80f9b
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (4S,4aR,5R,8aS)-5-hydroxy-4a,8,8-trimethylspiro[1,3,5,6,7,8a-hexahydronaphthalene-4,5'-furan]-2,2'-dione
• SMILES (Canonical): CC1(CCC(C2(C1CC(=O)CC23C=CC(=O)O3)C)O)C
• SMILES (Isomeric): C[C@]12[C@@H](CCC([C@@H]1CC(=O)C[C@]23C=CC(=O)O3)(C)C)O
• InChI: InChI=1S/C16H22O4/c1-14(2)6-4-12(18)15(3)11(14)8-10(17)9-16(15)7-5-13(19)20-16/h5,7,11-12,18H,4,6,8-9H2,1-3H3/t11-,12+,15+,16+/m0/s1
• InChI Key: IPELMMVREMPOCE-UAXWRAGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.34 g/mol
• Exact Mass: 278.15180918 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9898	98.98%
Caco-2	+	0.7732	77.32%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7748	77.48%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	+	0.8396	83.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.9351	93.51%
P-glycoprotein inhibitior	-	0.9377	93.77%
P-glycoprotein substrate	-	0.8520	85.20%
CYP3A4 substrate	+	0.6173	61.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8853	88.53%
CYP3A4 inhibition	-	0.6581	65.81%
CYP2C9 inhibition	-	0.8835	88.35%
CYP2C19 inhibition	-	0.8526	85.26%
CYP2D6 inhibition	-	0.9748	97.48%
CYP1A2 inhibition	-	0.8477	84.77%
CYP2C8 inhibition	-	0.8386	83.86%
CYP inhibitory promiscuity	-	0.9732	97.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5906	59.06%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8991	89.91%
Skin irritation	+	0.6151	61.51%
Skin corrosion	-	0.8468	84.68%
Ames mutagenesis	-	0.7670	76.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6629	66.29%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5301	53.01%
skin sensitisation	-	0.8000	80.00%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6313	63.13%
Acute Oral Toxicity (c)	I	0.5155	51.55%
Estrogen receptor binding	-	0.4857	48.57%
Androgen receptor binding	-	0.5397	53.97%
Thyroid receptor binding	-	0.5958	59.58%
Glucocorticoid receptor binding	+	0.5513	55.13%
Aromatase binding	+	0.6167	61.67%
PPAR gamma	+	0.5221	52.21%
Honey bee toxicity	-	0.9358	93.58%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9926	99.26%

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	94.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.87%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.21%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.87%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.02%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.73%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.37%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.25%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.19%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.74%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	80.32%	94.75%

Plants that contains it

• Taiwania cryptomerioides

Cross-Links

• PubChem: 101725709
• LOTUS: LTS0154179
• wikiData: Q105117203