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

Details

• Internal ID: 05b65a51-0584-4d40-8994-d08b028adc82
• 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-4-yl)ethyl]-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC2C(C1CCC3=CCOC3=O)(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@]([C@H]1CCC3=CCOC3=O)(CCC[C@@]2(C)C(=O)O)C
• InChI: InChI=1S/C20H28O4/c1-13-5-8-16-19(2,10-4-11-20(16,3)18(22)23)15(13)7-6-14-9-12-24-17(14)21/h5,9,15-16H,4,6-8,10-12H2,1-3H3,(H,22,23)/t15-,16+,19+,20+/m0/s1
• InChI Key: LHPTTZHNFUTODF-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: 3.90
• 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	+	0.6625	66.25%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8006	80.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7863	78.63%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5480	54.80%
BSEP inhibitior	+	0.7363	73.63%
P-glycoprotein inhibitior	-	0.6632	66.32%
P-glycoprotein substrate	-	0.7720	77.20%
CYP3A4 substrate	+	0.6209	62.09%
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	-	0.7081	70.81%
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	-	0.9323	93.23%
Skin irritation	+	0.4930	49.30%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5350	53.50%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5194	51.94%
skin sensitisation	-	0.8002	80.02%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5101	51.01%
Acute Oral Toxicity (c)	III	0.6509	65.09%
Estrogen receptor binding	+	0.6747	67.47%
Androgen receptor binding	+	0.5391	53.91%
Thyroid receptor binding	+	0.6773	67.73%
Glucocorticoid receptor binding	+	0.8185	81.85%
Aromatase binding	+	0.6572	65.72%
PPAR gamma	+	0.5324	53.24%
Honey bee toxicity	-	0.9370	93.70%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	96.12%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.28%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.09%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.84%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.14%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.87%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.65%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.46%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.27%	96.09%

Plants that contains it

• Gutierrezia resinosa

Cross-Links

• PubChem: 162979874
• LOTUS: LTS0254703
• wikiData: Q105151890