2-[(2R,6S,8R,8aR)-6-acetyloxy-8,8a-dimethyl-7-oxo-1,2,3,4,6,8-hexahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: c7213bce-7329-4b50-9708-5ed8068e36f7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: 2-[(2R,6S,8R,8aR)-6-acetyloxy-8,8a-dimethyl-7-oxo-1,2,3,4,6,8-hexahydronaphthalen-2-yl]prop-2-enoic acid
• InChI: InChI=1S/C17H22O5/c1-9(16(20)21)12-5-6-13-7-14(22-11(3)18)15(19)10(2)17(13,4)8-12/h7,10,12,14H,1,5-6,8H2,2-4H3,(H,20,21)/t10-,12+,14-,17+/m0/s1
• InChI Key: JKWVGSLQMFMFGK-PUKHHJTISA-N
• Popularity: 2 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: 2.60
• 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	+	0.9837	98.37%
Caco-2	+	0.6647	66.47%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8171	81.71%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.8630	86.30%
OATP1B3 inhibitior	-	0.2439	24.39%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.7423	74.23%
P-glycoprotein inhibitior	-	0.8194	81.94%
P-glycoprotein substrate	-	0.8167	81.67%
CYP3A4 substrate	+	0.6034	60.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8990	89.90%
CYP3A4 inhibition	-	0.7161	71.61%
CYP2C9 inhibition	-	0.8200	82.00%
CYP2C19 inhibition	-	0.8676	86.76%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	+	0.5339	53.39%
CYP2C8 inhibition	-	0.6204	62.04%
CYP inhibitory promiscuity	-	0.9266	92.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.6373	63.73%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9268	92.68%
Skin irritation	+	0.6303	63.03%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6555	65.55%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5323	53.23%
skin sensitisation	-	0.6656	66.56%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5571	55.71%
Acute Oral Toxicity (c)	III	0.6874	68.74%
Estrogen receptor binding	+	0.5909	59.09%
Androgen receptor binding	-	0.5185	51.85%
Thyroid receptor binding	-	0.5303	53.03%
Glucocorticoid receptor binding	+	0.6434	64.34%
Aromatase binding	-	0.5794	57.94%
PPAR gamma	-	0.5506	55.06%
Honey bee toxicity	-	0.8606	86.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.65%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.68%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.88%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.53%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	87.84%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.73%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.06%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.82%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.97%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	84.83%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.08%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.46%	95.89%

Plants that contains it

• Haeckeria punctulata
• Ozothamnus pholidotus

Cross-Links

• PubChem: 15699279
• LOTUS: LTS0045910
• wikiData: Q104391883