[9-(Chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 4-acetyloxy-2-methylbut-2-enoate

Details

• Internal ID: f57b150b-b704-4161-ad4f-e66b883eabe1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 4-acetyloxy-2-methylbut-2-enoate
• InChI: InChI=1S/C22H27ClO8/c1-10(5-6-29-13(4)24)20(26)30-15-7-11(2)14-8-16(25)22(28,9-23)18(14)19-17(15)12(3)21(27)31-19/h5,14-19,25,28H,2-3,6-9H2,1,4H3
• InChI Key: HHJVKRNLEVFVRT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₇ClO₈
• Molecular Weight: 454.90 g/mol
• Exact Mass: 454.1394455 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9489	94.89%
Caco-2	-	0.8019	80.19%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7151	71.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6931	69.31%
P-glycoprotein inhibitior	-	0.5921	59.21%
P-glycoprotein substrate	-	0.5280	52.80%
CYP3A4 substrate	+	0.6954	69.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8995	89.95%
CYP3A4 inhibition	-	0.8523	85.23%
CYP2C9 inhibition	-	0.7866	78.66%
CYP2C19 inhibition	-	0.7182	71.82%
CYP2D6 inhibition	-	0.9050	90.50%
CYP1A2 inhibition	-	0.7508	75.08%
CYP2C8 inhibition	-	0.5578	55.78%
CYP inhibitory promiscuity	-	0.9516	95.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8444	84.44%
Carcinogenicity (trinary)	Non-required	0.5828	58.28%
Eye corrosion	-	0.9801	98.01%
Eye irritation	-	0.9208	92.08%
Skin irritation	-	0.6660	66.60%
Skin corrosion	-	0.9140	91.40%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5710	57.10%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8208	82.08%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.9307	93.07%
Acute Oral Toxicity (c)	III	0.4226	42.26%
Estrogen receptor binding	+	0.6787	67.87%
Androgen receptor binding	+	0.6566	65.66%
Thyroid receptor binding	-	0.5102	51.02%
Glucocorticoid receptor binding	+	0.6195	61.95%
Aromatase binding	+	0.5286	52.86%
PPAR gamma	+	0.5717	57.17%
Honey bee toxicity	-	0.5800	58.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9870	98.70%

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	97.57%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.24%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.81%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.52%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.03%	89.34%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.80%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.75%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.84%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.07%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.25%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	84.37%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.54%	89.00%
CHEMBL5957	P21589	5'-nucleotidase	80.47%	97.78%

Plants that contains it

• Centaurea scoparia

Cross-Links

• PubChem: 163054306
• LOTUS: LTS0193787
• wikiData: Q105028334