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

Details

• Internal ID: 58c33a96-60b0-474b-88be-2308ccd09806
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: [(5S,6R,8S,8aR)-5-(2-acetyloxypropan-2-yl)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-6-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC1CC(C(CC2=C(C(=O)CC12)C)C(C)(C)OC(=O)C)OC(=O)C(=C)C
• 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)OC(=O)C(=C)C
• InChI: InChI=1S/C21H30O5/c1-11(2)20(24)25-19-8-12(3)15-10-18(23)13(4)16(15)9-17(19)21(6,7)26-14(5)22/h12,15,17,19H,1,8-10H2,2-7H3/t12-,15+,17-,19+/m0/s1
• InChI Key: JMIQQXQWNZHMDB-MJFFMMMISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.50 g/mol
• Exact Mass: 362.20932405 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.77
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.7034	70.34%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6956	69.56%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.9224	92.24%
OATP1B3 inhibitior	-	0.2223	22.23%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5814	58.14%
P-glycoprotein inhibitior	+	0.6150	61.50%
P-glycoprotein substrate	-	0.6991	69.91%
CYP3A4 substrate	+	0.6181	61.81%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9017	90.17%
CYP3A4 inhibition	-	0.6785	67.85%
CYP2C9 inhibition	-	0.7215	72.15%
CYP2C19 inhibition	-	0.7772	77.72%
CYP2D6 inhibition	-	0.9625	96.25%
CYP1A2 inhibition	-	0.7160	71.60%
CYP2C8 inhibition	-	0.7025	70.25%
CYP inhibitory promiscuity	-	0.9443	94.43%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5719	57.19%
Eye corrosion	-	0.9723	97.23%
Eye irritation	-	0.7580	75.80%
Skin irritation	-	0.5271	52.71%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7221	72.21%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6940	69.40%
skin sensitisation	-	0.5902	59.02%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4637	46.37%
Acute Oral Toxicity (c)	II	0.4016	40.16%
Estrogen receptor binding	+	0.7499	74.99%
Androgen receptor binding	-	0.5061	50.61%
Thyroid receptor binding	+	0.5768	57.68%
Glucocorticoid receptor binding	+	0.6663	66.63%
Aromatase binding	-	0.5738	57.38%
PPAR gamma	+	0.6468	64.68%
Honey bee toxicity	-	0.6719	67.19%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
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	94.08%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.20%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.60%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.25%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.09%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.77%	85.14%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.86%	90.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.80%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.77%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.53%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.77%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.32%	89.00%

Plants that contains it

• Torilis japonica

Cross-Links

• PubChem: 25112481
• LOTUS: LTS0031204
• wikiData: Q105131449