(2Z)-2-[(1R,5R,8S,8aR)-5-acetyloxy-1-hydroxy-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1H-naphthalen-2-ylidene]propanoic acid

Details

• Internal ID: 0679b308-c2ab-4d60-a8fa-141e9d850b3d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (2Z)-2-[(1R,5R,8S,8aR)-5-acetyloxy-1-hydroxy-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydro-1H-naphthalen-2-ylidene]propanoic acid
• InChI: InChI=1S/C17H22O6/c1-8-5-6-13(23-10(3)18)11-7-12(19)14(9(2)16(21)22)15(20)17(8,11)4/h7-8,13,15,20H,5-6H2,1-4H3,(H,21,22)/b14-9+/t8-,13+,15-,17+/m0/s1
• InChI Key: SFWDFSRSGGEBJN-YVGGPEGWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.14163842 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.63
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	+	0.5574	55.74%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7996	79.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8868	88.68%
OATP1B3 inhibitior	+	0.8441	84.41%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.7769	77.69%
P-glycoprotein inhibitior	-	0.8657	86.57%
P-glycoprotein substrate	-	0.7983	79.83%
CYP3A4 substrate	+	0.5888	58.88%
CYP2C9 substrate	-	0.7791	77.91%
CYP2D6 substrate	-	0.9072	90.72%
CYP3A4 inhibition	-	0.7993	79.93%
CYP2C9 inhibition	-	0.8659	86.59%
CYP2C19 inhibition	-	0.9382	93.82%
CYP2D6 inhibition	-	0.9228	92.28%
CYP1A2 inhibition	+	0.5744	57.44%
CYP2C8 inhibition	-	0.8532	85.32%
CYP inhibitory promiscuity	-	0.8731	87.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5330	53.30%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9399	93.99%
Skin irritation	+	0.6295	62.95%
Skin corrosion	-	0.9191	91.91%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4417	44.17%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	-	0.7029	70.29%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.4726	47.26%
Acute Oral Toxicity (c)	III	0.5895	58.95%
Estrogen receptor binding	+	0.7556	75.56%
Androgen receptor binding	+	0.6453	64.53%
Thyroid receptor binding	+	0.5250	52.50%
Glucocorticoid receptor binding	+	0.7047	70.47%
Aromatase binding	-	0.5179	51.79%
PPAR gamma	+	0.5296	52.96%
Honey bee toxicity	-	0.8925	89.25%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9877	98.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.05%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.92%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.09%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.98%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.94%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.12%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.02%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.64%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.34%	93.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.11%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.19%	95.56%

Plants that contains it

• Ligularia sagitta

Cross-Links

• PubChem: 102586048
• LOTUS: LTS0015317
• wikiData: Q105252100