(1R,2R,4aR,8aR)-1,4a,5-trimethyl-1-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylic acid

Details

• Internal ID: 736b9855-6d7b-49d6-8710-b87c6ee86e33
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,2R,4aR,8aR)-1,4a,5-trimethyl-1-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylic acid
• SMILES (Canonical): CC1=CCCC2C1(CCC(C2(C)CCC3=CC(=O)OC3)C(=O)O)C
• SMILES (Isomeric): CC1=CCC[C@H]2[C@]1(CC[C@H]([C@]2(C)CCC3=CC(=O)OC3)C(=O)O)C
• InChI: InChI=1S/C20H28O4/c1-13-5-4-6-16-19(13,2)10-8-15(18(22)23)20(16,3)9-7-14-11-17(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: KZIDMGQRXAFSCG-FVCZOJIISA-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: 3.60
• 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	+	0.6872	68.72%
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	+	0.9013	90.13%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5480	54.80%
BSEP inhibitior	+	0.7638	76.38%
P-glycoprotein inhibitior	-	0.6496	64.96%
P-glycoprotein substrate	-	0.7529	75.29%
CYP3A4 substrate	+	0.6292	62.92%
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	-	0.5702	57.02%
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	-	0.9090	90.90%
Skin irritation	+	0.4930	49.30%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4018	40.18%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5926	59.26%
skin sensitisation	-	0.8002	80.02%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5112	51.12%
Acute Oral Toxicity (c)	III	0.6509	65.09%
Estrogen receptor binding	+	0.7289	72.89%
Androgen receptor binding	+	0.7067	70.67%
Thyroid receptor binding	+	0.5708	57.08%
Glucocorticoid receptor binding	+	0.7362	73.62%
Aromatase binding	+	0.6201	62.01%
PPAR gamma	+	0.6236	62.36%
Honey bee toxicity	-	0.9044	90.44%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
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	95.81%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.79%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.65%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.79%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.73%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.61%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.52%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.50%	86.33%
CHEMBL5028	O14672	ADAM10	84.01%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.00%	93.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.89%	96.09%

Plants that contains it

• Diplostephium floribundum

Cross-Links

• PubChem: 101618880
• LOTUS: LTS0241670
• wikiData: Q105148165