5-(chloromethyl)-5,7,8a-trihydroxy-1,8-dimethylidene-4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one

Details

• Internal ID: 2ad1a4bf-ea86-468a-b315-e41237f65feb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 5-(chloromethyl)-5,7,8a-trihydroxy-1,8-dimethylidene-4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one
• SMILES (Canonical): C=C1C(CC2C1(CC3C(CC2(CCl)O)OC(=O)C3=C)O)O
• SMILES (Isomeric): C=C1C(CC2C1(CC3C(CC2(CCl)O)OC(=O)C3=C)O)O
• InChI: InChI=1S/C15H19ClO5/c1-7-9-4-15(20)8(2)10(17)3-12(15)14(19,6-16)5-11(9)21-13(7)18/h9-12,17,19-20H,1-6H2
• InChI Key: PXCLIGUGCAGFAN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₉ClO₅
• Molecular Weight: 314.76 g/mol
• Exact Mass: 314.0921014 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9615	96.15%
Caco-2	-	0.8087	80.87%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5769	57.69%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9068	90.68%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9677	96.77%
P-glycoprotein inhibitior	-	0.9264	92.64%
P-glycoprotein substrate	-	0.7915	79.15%
CYP3A4 substrate	+	0.5968	59.68%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8224	82.24%
CYP3A4 inhibition	-	0.8645	86.45%
CYP2C9 inhibition	-	0.8727	87.27%
CYP2C19 inhibition	-	0.7956	79.56%
CYP2D6 inhibition	-	0.9142	91.42%
CYP1A2 inhibition	-	0.8356	83.56%
CYP2C8 inhibition	-	0.7714	77.14%
CYP inhibitory promiscuity	-	0.9132	91.32%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8444	84.44%
Carcinogenicity (trinary)	Non-required	0.4852	48.52%
Eye corrosion	-	0.9699	96.99%
Eye irritation	-	0.9092	90.92%
Skin irritation	-	0.6645	66.45%
Skin corrosion	-	0.9004	90.04%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6687	66.87%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6616	66.16%
skin sensitisation	-	0.7784	77.84%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7477	74.77%
Acute Oral Toxicity (c)	III	0.4560	45.60%
Estrogen receptor binding	+	0.8260	82.60%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5265	52.65%
Glucocorticoid receptor binding	+	0.8102	81.02%
Aromatase binding	+	0.6037	60.37%
PPAR gamma	-	0.5183	51.83%
Honey bee toxicity	-	0.6999	69.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9591	95.91%

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	95.99%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.16%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.89%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	91.62%	98.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.83%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.00%	89.34%
CHEMBL221	P23219	Cyclooxygenase-1	84.13%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.64%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.43%	96.95%
CHEMBL3572	P11597	Cholesteryl ester transfer protein	80.24%	92.67%

Plants that contains it

• Arctotis fastuosa

Cross-Links

• PubChem: 162907475
• LOTUS: LTS0000692
• wikiData: Q105216102