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

Details

• Internal ID: a872c84a-5a08-4461-9f73-aa9bc3338cd9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: 2-[(2R,7R,8R,8aR)-7-acetyloxy-8,8a-dimethyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1C(C(=O)C=C2C1(CC(CC2)C(=C)C(=O)O)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@H](C(=O)C=C2[C@@]1(C[C@@H](CC2)C(=C)C(=O)O)C)OC(=O)C
• InChI: InChI=1S/C17H22O5/c1-9(16(20)21)12-5-6-13-7-14(19)15(22-11(3)18)10(2)17(13,4)8-12/h7,10,12,15H,1,5-6,8H2,2-4H3,(H,20,21)/t10-,12+,15+,17+/m0/s1
• InChI Key: KOQZRRFLUNPTKN-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: 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	+	0.6839	68.39%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8171	81.71%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.8799	87.99%
OATP1B3 inhibitior	-	0.2439	24.39%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.7329	73.29%
P-glycoprotein inhibitior	-	0.8111	81.11%
P-glycoprotein substrate	-	0.7389	73.89%
CYP3A4 substrate	+	0.6212	62.12%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9141	91.41%
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	-	0.6604	66.04%
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	-	0.8916	89.16%
Skin irritation	+	0.6303	63.03%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5300	53.00%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5981	59.81%
skin sensitisation	-	0.6656	66.56%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5219	52.19%
Acute Oral Toxicity (c)	III	0.6874	68.74%
Estrogen receptor binding	+	0.6709	67.09%
Androgen receptor binding	+	0.5514	55.14%
Thyroid receptor binding	-	0.5763	57.63%
Glucocorticoid receptor binding	+	0.6954	69.54%
Aromatase binding	+	0.5955	59.55%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8191	81.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	97.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.62%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.03%	91.49%
CHEMBL2581	P07339	Cathepsin D	89.69%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.27%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.17%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.73%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.48%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.61%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.61%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.87%	94.62%

Plants that contains it

• Ozothamnus pholidotus

Cross-Links

• PubChem: 15699286
• LOTUS: LTS0002977
• wikiData: Q105143954