5-[2-(2-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: 574ee43a-da6a-44c7-b2c2-52af29696c3f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 5-[2-(2-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC2C(C1CCC3=CC(=O)OC3O)(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): CC1=CCC2C(C1CCC3=CC(=O)OC3O)(CCCC2(C)C(=O)O)C
• InChI: InChI=1S/C20H28O5/c1-12-5-8-15-19(2,9-4-10-20(15,3)18(23)24)14(12)7-6-13-11-16(21)25-17(13)22/h5,11,14-15,17,22H,4,6-10H2,1-3H3,(H,23,24)
• InChI Key: UUEVWZUUWQVANP-UHFFFAOYSA-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): 83.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9832	98.32%
Caco-2	+	0.5327	53.27%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7122	71.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7465	74.65%
OATP1B3 inhibitior	+	0.8389	83.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6303	63.03%
BSEP inhibitior	+	0.8116	81.16%
P-glycoprotein inhibitior	-	0.8123	81.23%
P-glycoprotein substrate	-	0.7428	74.28%
CYP3A4 substrate	+	0.6328	63.28%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.9000	90.00%
CYP3A4 inhibition	-	0.6594	65.94%
CYP2C9 inhibition	-	0.8278	82.78%
CYP2C19 inhibition	-	0.8723	87.23%
CYP2D6 inhibition	-	0.9460	94.60%
CYP1A2 inhibition	-	0.5928	59.28%
CYP2C8 inhibition	-	0.7091	70.91%
CYP inhibitory promiscuity	-	0.8373	83.73%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5383	53.83%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9220	92.20%
Skin irritation	+	0.5659	56.59%
Skin corrosion	-	0.9216	92.16%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4910	49.10%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5071	50.71%
skin sensitisation	-	0.7076	70.76%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5820	58.20%
Acute Oral Toxicity (c)	I	0.3667	36.67%
Estrogen receptor binding	+	0.8489	84.89%
Androgen receptor binding	+	0.5536	55.36%
Thyroid receptor binding	+	0.6484	64.84%
Glucocorticoid receptor binding	+	0.8313	83.13%
Aromatase binding	+	0.7506	75.06%
PPAR gamma	+	0.6707	67.07%
Honey bee toxicity	-	0.9091	90.91%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	94.13%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.57%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.57%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.26%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.90%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.01%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.67%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.28%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.75%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.23%	93.04%

Plants that contains it

• Gutierrezia resinosa

Cross-Links

• PubChem: 162885199
• LOTUS: LTS0198133
• wikiData: Q105279279