[5-(chloromethyl)-5,8a-dihydroxy-1,8-dimethylidene-2-oxo-4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-7-yl] propanoate

Details

• Internal ID: bc42ca0b-aca9-4736-93f0-12d8305909e7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [5-(chloromethyl)-5,8a-dihydroxy-1,8-dimethylidene-2-oxo-4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-7-yl] propanoate
• InChI: InChI=1S/C18H23ClO6/c1-4-15(20)24-12-5-14-17(22,8-19)7-13-11(9(2)16(21)25-13)6-18(14,23)10(12)3/h11-14,22-23H,2-8H2,1H3
• InChI Key: UTFMYUDTIZFQDE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₃ClO₆
• Molecular Weight: 370.80 g/mol
• Exact Mass: 370.1183161 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9700	97.00%
Caco-2	-	0.7803	78.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6097	60.97%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.8552	85.52%
OATP1B3 inhibitior	+	0.9522	95.22%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8788	87.88%
P-glycoprotein inhibitior	-	0.7565	75.65%
P-glycoprotein substrate	-	0.6213	62.13%
CYP3A4 substrate	+	0.6605	66.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8929	89.29%
CYP3A4 inhibition	-	0.7911	79.11%
CYP2C9 inhibition	-	0.7667	76.67%
CYP2C19 inhibition	-	0.7404	74.04%
CYP2D6 inhibition	-	0.9090	90.90%
CYP1A2 inhibition	-	0.8108	81.08%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8595	85.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8244	82.44%
Carcinogenicity (trinary)	Non-required	0.5103	51.03%
Eye corrosion	-	0.9761	97.61%
Eye irritation	-	0.9302	93.02%
Skin irritation	-	0.6764	67.64%
Skin corrosion	-	0.8981	89.81%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4863	48.63%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5324	53.24%
skin sensitisation	-	0.7888	78.88%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7045	70.45%
Acute Oral Toxicity (c)	III	0.4491	44.91%
Estrogen receptor binding	+	0.7157	71.57%
Androgen receptor binding	-	0.4924	49.24%
Thyroid receptor binding	+	0.6423	64.23%
Glucocorticoid receptor binding	+	0.8564	85.64%
Aromatase binding	+	0.5538	55.38%
PPAR gamma	+	0.6641	66.41%
Honey bee toxicity	-	0.7390	73.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9843	98.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.99%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.78%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.90%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.13%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.88%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.40%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	88.52%	90.17%
CHEMBL299	P17252	Protein kinase C alpha	87.76%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	83.03%	97.79%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.63%	91.24%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.55%	89.34%

Plants that contains it

• Arctotis fastuosa

Cross-Links

• PubChem: 163070763
• LOTUS: LTS0103414
• wikiData: Q105278736