2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enyl acetate

Details

• Internal ID: 5f79645e-3090-4a64-bb7d-2d753621db50
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: 2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enyl acetate
• SMILES (Canonical): CC1CCC(CC2=C(C(=O)CC12)C)C(=C)COC(=O)C
• SMILES (Isomeric): C[C@@H]1CC[C@H](CC2=C(C(=O)C[C@H]12)C)C(=C)COC(=O)C
• InChI: InChI=1S/C17H24O3/c1-10-5-6-14(11(2)9-20-13(4)18)7-16-12(3)17(19)8-15(10)16/h10,14-15H,2,5-9H2,1,3-4H3/t10-,14-,15-/m1/s1
• InChI Key: GZPURHLBWSYNHJ-VCTAVGKDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.40 g/mol
• Exact Mass: 276.17254462 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.45
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.7642	76.42%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7582	75.82%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9029	90.29%
OATP1B3 inhibitior	+	0.9182	91.82%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7122	71.22%
P-glycoprotein inhibitior	-	0.6811	68.11%
P-glycoprotein substrate	-	0.7877	78.77%
CYP3A4 substrate	+	0.5427	54.27%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9017	90.17%
CYP3A4 inhibition	-	0.8194	81.94%
CYP2C9 inhibition	-	0.8034	80.34%
CYP2C19 inhibition	-	0.7166	71.66%
CYP2D6 inhibition	-	0.9063	90.63%
CYP1A2 inhibition	-	0.6282	62.82%
CYP2C8 inhibition	-	0.6916	69.16%
CYP inhibitory promiscuity	-	0.8723	87.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6108	61.08%
Eye corrosion	-	0.9692	96.92%
Eye irritation	+	0.6641	66.41%
Skin irritation	-	0.6097	60.97%
Skin corrosion	-	0.9692	96.92%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6897	68.97%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6428	64.28%
skin sensitisation	-	0.7081	70.81%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4911	49.11%
Acute Oral Toxicity (c)	III	0.7311	73.11%
Estrogen receptor binding	-	0.6305	63.05%
Androgen receptor binding	-	0.4828	48.28%
Thyroid receptor binding	-	0.6476	64.76%
Glucocorticoid receptor binding	-	0.4668	46.68%
Aromatase binding	-	0.7950	79.50%
PPAR gamma	-	0.6653	66.53%
Honey bee toxicity	-	0.9027	90.27%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9970	99.70%

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	94.53%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.52%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.77%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.20%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.18%	94.80%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.29%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.11%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	85.46%	83.82%
CHEMBL340	P08684	Cytochrome P450 3A4	83.70%	91.19%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.78%	93.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.47%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.02%	95.56%

Plants that contains it

• Jungia stuebelii

Cross-Links

• PubChem: 163001895
• LOTUS: LTS0139348
• wikiData: Q105024505