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

Details

• Internal ID: aafc088f-9ec4-4bab-a09f-bbb1d5c7d3ac
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: 2-[(5S,6R,8S,8aR)-6-hydroxy-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]propan-2-yl acetate
• SMILES (Canonical): CC1CC(C(CC2=C(C(=O)CC12)C)C(C)(C)OC(=O)C)O
• SMILES (Isomeric): C[C@H]1C[C@H]([C@H](CC2=C(C(=O)C[C@H]12)C)C(C)(C)OC(=O)C)O
• InChI: InChI=1S/C17H26O4/c1-9-6-16(20)14(17(4,5)21-11(3)18)7-13-10(2)15(19)8-12(9)13/h9,12,14,16,20H,6-8H2,1-5H3/t9-,12+,14-,16+/m0/s1
• InChI Key: PSVQRRSHJWNFPZ-UODBANLJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.5742	57.42%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.9297	92.97%
OATP1B3 inhibitior	+	0.8677	86.77%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7234	72.34%
P-glycoprotein inhibitior	-	0.7055	70.55%
P-glycoprotein substrate	-	0.7893	78.93%
CYP3A4 substrate	+	0.5694	56.94%
CYP2C9 substrate	-	0.7791	77.91%
CYP2D6 substrate	-	0.8952	89.52%
CYP3A4 inhibition	-	0.7661	76.61%
CYP2C9 inhibition	-	0.6979	69.79%
CYP2C19 inhibition	-	0.8353	83.53%
CYP2D6 inhibition	-	0.9655	96.55%
CYP1A2 inhibition	-	0.7898	78.98%
CYP2C8 inhibition	-	0.8553	85.53%
CYP inhibitory promiscuity	-	0.9758	97.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5877	58.77%
Eye corrosion	-	0.9833	98.33%
Eye irritation	-	0.7830	78.30%
Skin irritation	+	0.5129	51.29%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5465	54.65%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.7027	70.27%
skin sensitisation	-	0.6800	68.00%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6889	68.89%
Acute Oral Toxicity (c)	II	0.3934	39.34%
Estrogen receptor binding	+	0.6439	64.39%
Androgen receptor binding	+	0.5345	53.45%
Thyroid receptor binding	+	0.5501	55.01%
Glucocorticoid receptor binding	+	0.5829	58.29%
Aromatase binding	-	0.7078	70.78%
PPAR gamma	-	0.5814	58.14%
Honey bee toxicity	-	0.8389	83.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.82%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.22%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.09%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.87%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.83%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.39%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.75%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.02%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.26%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.56%	99.23%

Plants that contains it

• Daucus carota

Cross-Links

• PubChem: 45102165
• LOTUS: LTS0022171
• wikiData: Q105214418