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

Details

• Internal ID: 83679ff0-d8f2-464b-83e3-38435011b53d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,4aR,5S,8aR)-1,4a,6-trimethyl-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC2C(C1CCC3=CC(=O)OC3)(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@]([C@H]1CCC3=CC(=O)OC3)(CCC[C@@]2(C)C(=O)O)C
• InChI: InChI=1S/C20H28O4/c1-13-5-8-16-19(2,9-4-10-20(16,3)18(22)23)15(13)7-6-14-11-17(21)24-12-14/h5,11,15-16H,4,6-10,12H2,1-3H3,(H,22,23)/t15-,16+,19+,20+/m0/s1
• InChI Key: ZATVCCDJRSRELS-LNKGRISISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9894	98.94%
Caco-2	+	0.5978	59.78%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8006	80.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7789	77.89%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5480	54.80%
BSEP inhibitior	+	0.7864	78.64%
P-glycoprotein inhibitior	-	0.7427	74.27%
P-glycoprotein substrate	-	0.7039	70.39%
CYP3A4 substrate	+	0.6275	62.75%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.9179	91.79%
CYP3A4 inhibition	-	0.5844	58.44%
CYP2C9 inhibition	-	0.7358	73.58%
CYP2C19 inhibition	-	0.8409	84.09%
CYP2D6 inhibition	-	0.9147	91.47%
CYP1A2 inhibition	-	0.6515	65.15%
CYP2C8 inhibition	-	0.6036	60.36%
CYP inhibitory promiscuity	-	0.8187	81.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6267	62.67%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9170	91.70%
Skin irritation	+	0.4930	49.30%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4004	40.04%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5431	54.31%
skin sensitisation	-	0.8002	80.02%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4682	46.82%
Acute Oral Toxicity (c)	III	0.6509	65.09%
Estrogen receptor binding	+	0.6719	67.19%
Androgen receptor binding	+	0.6046	60.46%
Thyroid receptor binding	+	0.5797	57.97%
Glucocorticoid receptor binding	+	0.7837	78.37%
Aromatase binding	+	0.6217	62.17%
PPAR gamma	+	0.6460	64.60%
Honey bee toxicity	-	0.9075	90.75%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	97.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.06%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.76%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.73%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.06%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.26%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.18%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.91%	96.09%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.44%	96.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.16%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.28%	94.45%

Plants that contains it

• Gutierrezia resinosa

Cross-Links

• PubChem: 162998497
• LOTUS: LTS0273548
• wikiData: Q105370112