2-[(2R,5R,8R,8aR)-5-acetyloxy-8,8a-dimethyl-7-oxo-1,2,3,5,6,8-hexahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: ed9242df-ed1f-4f9b-951a-3abab27c1bad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: 2-[(2R,5R,8R,8aR)-5-acetyloxy-8,8a-dimethyl-7-oxo-1,2,3,5,6,8-hexahydronaphthalen-2-yl]prop-2-enoic acid
• InChI: InChI=1S/C17H22O5/c1-9(16(20)21)12-5-6-13-15(22-11(3)18)7-14(19)10(2)17(13,4)8-12/h6,10,12,15H,1,5,7-8H2,2-4H3,(H,20,21)/t10-,12+,15+,17+/m0/s1
• InChI Key: GPKGVPQKVUPOKJ-RGBHZWMGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	+	0.5989	59.89%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7338	73.38%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8855	88.55%
OATP1B3 inhibitior	-	0.2186	21.86%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5191	51.91%
P-glycoprotein inhibitior	-	0.8674	86.74%
P-glycoprotein substrate	-	0.7495	74.95%
CYP3A4 substrate	+	0.5899	58.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8990	89.90%
CYP3A4 inhibition	-	0.6454	64.54%
CYP2C9 inhibition	-	0.8829	88.29%
CYP2C19 inhibition	-	0.8792	87.92%
CYP2D6 inhibition	-	0.9520	95.20%
CYP1A2 inhibition	-	0.5827	58.27%
CYP2C8 inhibition	-	0.6143	61.43%
CYP inhibitory promiscuity	-	0.9196	91.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9183	91.83%
Carcinogenicity (trinary)	Non-required	0.5765	57.65%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8818	88.18%
Skin irritation	+	0.5672	56.72%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.5728	57.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.6426	64.26%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6066	60.66%
skin sensitisation	-	0.6618	66.18%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7558	75.58%
Acute Oral Toxicity (c)	III	0.5246	52.46%
Estrogen receptor binding	-	0.5762	57.62%
Androgen receptor binding	-	0.4857	48.57%
Thyroid receptor binding	-	0.6195	61.95%
Glucocorticoid receptor binding	+	0.5533	55.33%
Aromatase binding	-	0.5120	51.20%
PPAR gamma	-	0.6315	63.15%
Honey bee toxicity	-	0.7559	75.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5350	53.50%
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
CHEMBL4040	P28482	MAP kinase ERK2	96.65%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.67%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.47%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.42%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.57%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.18%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	85.32%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.45%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.34%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.30%	89.00%
CHEMBL4208	P20618	Proteasome component C5	80.54%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	80.15%	91.49%

Plants that contains it

• Ozothamnus pholidotus

Cross-Links

• PubChem: 15699268
• LOTUS: LTS0138218
• wikiData: Q105014906