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

Details

• Internal ID: b8da9b1e-11ef-4f8f-86ef-2d7b90c21264
• 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 3-hydroxy-3-methylbutanoate
• SMILES (Canonical): CC1CCC(CC2=C(C(=O)CC12)C)C(=C)COC(=O)CC(C)(C)O
• SMILES (Isomeric): C[C@@H]1CC[C@H](CC2=C(C(=O)C[C@H]12)C)C(=C)COC(=O)CC(C)(C)O
• InChI: InChI=1S/C20H30O4/c1-12-6-7-15(8-17-14(3)18(21)9-16(12)17)13(2)11-24-19(22)10-20(4,5)23/h12,15-16,23H,2,6-11H2,1,3-5H3/t12-,15-,16-/m1/s1
• InChI Key: GIJMOEIBTVWHCV-DAXOMENPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9899	98.99%
Caco-2	+	0.6162	61.62%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7738	77.38%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8898	88.98%
OATP1B3 inhibitior	+	0.8854	88.54%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7347	73.47%
P-glycoprotein inhibitior	-	0.6726	67.26%
P-glycoprotein substrate	-	0.7086	70.86%
CYP3A4 substrate	+	0.5935	59.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9113	91.13%
CYP3A4 inhibition	-	0.8239	82.39%
CYP2C9 inhibition	-	0.6616	66.16%
CYP2C19 inhibition	-	0.8896	88.96%
CYP2D6 inhibition	-	0.9469	94.69%
CYP1A2 inhibition	-	0.7587	75.87%
CYP2C8 inhibition	-	0.5849	58.49%
CYP inhibitory promiscuity	-	0.9651	96.51%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.7890	78.90%
Skin irritation	+	0.5796	57.96%
Skin corrosion	-	0.9510	95.10%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4852	48.52%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7053	70.53%
skin sensitisation	-	0.7809	78.09%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5875	58.75%
Acute Oral Toxicity (c)	III	0.4512	45.12%
Estrogen receptor binding	-	0.5845	58.45%
Androgen receptor binding	-	0.5686	56.86%
Thyroid receptor binding	+	0.5356	53.56%
Glucocorticoid receptor binding	-	0.4659	46.59%
Aromatase binding	-	0.6377	63.77%
PPAR gamma	-	0.5129	51.29%
Honey bee toxicity	-	0.9026	90.26%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9948	99.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.79%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	94.17%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.93%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.51%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.18%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.16%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.89%	93.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.75%	95.56%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.00%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.33%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.63%	95.89%

Plants that contains it

• Moscharia pinnatifida

Cross-Links

• PubChem: 15143877
• LOTUS: LTS0134276
• wikiData: Q105009033