[(3aR,4S,6aR,8S,9R,9aS,9bS)-8,9-dihydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-hydroxy-2-methylpropanoate

Details

• Internal ID: 88819ee0-ed07-459b-b881-13fcfa9095c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9R,9aS,9bS)-8,9-dihydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-hydroxy-2-methylpropanoate
• SMILES (Canonical): CC(CCl)(C(=O)OC1CC(=C)C2CC(C(C2C3C1C(=C)C(=O)O3)(CO)O)O)O
• SMILES (Isomeric): C[C@@](CCl)(C(=O)O[C@H]1CC(=C)[C@@H]2C[C@@H]([C@@]([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)(CO)O)O)O
• InChI: InChI=1S/C19H25ClO8/c1-8-4-11(27-17(24)18(3,25)6-20)13-9(2)16(23)28-15(13)14-10(8)5-12(22)19(14,26)7-21/h10-15,21-22,25-26H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18+,19+/m0/s1
• InChI Key: WHILMLOPVJMGGT-ONCJGSTBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₅ClO₈
• Molecular Weight: 416.80 g/mol
• Exact Mass: 416.1237954 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.33
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8504	85.04%
Caco-2	-	0.8060	80.60%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6318	63.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8360	83.60%
OATP1B3 inhibitior	+	0.9525	95.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8802	88.02%
P-glycoprotein inhibitior	-	0.7493	74.93%
P-glycoprotein substrate	-	0.5811	58.11%
CYP3A4 substrate	+	0.6973	69.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8639	86.39%
CYP3A4 inhibition	-	0.8938	89.38%
CYP2C9 inhibition	-	0.7897	78.97%
CYP2C19 inhibition	-	0.7641	76.41%
CYP2D6 inhibition	-	0.9070	90.70%
CYP1A2 inhibition	-	0.7996	79.96%
CYP2C8 inhibition	+	0.4588	45.88%
CYP inhibitory promiscuity	-	0.9383	93.83%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8244	82.44%
Carcinogenicity (trinary)	Non-required	0.5716	57.16%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.7118	71.18%
Skin corrosion	-	0.9209	92.09%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4281	42.81%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8468	84.68%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.8591	85.91%
Acute Oral Toxicity (c)	III	0.4783	47.83%
Estrogen receptor binding	+	0.6215	62.15%
Androgen receptor binding	+	0.6895	68.95%
Thyroid receptor binding	+	0.5774	57.74%
Glucocorticoid receptor binding	+	0.6884	68.84%
Aromatase binding	+	0.6306	63.06%
PPAR gamma	+	0.5434	54.34%
Honey bee toxicity	-	0.6878	68.78%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9675	96.75%

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	97.06%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.71%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	94.69%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.19%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.22%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.17%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.71%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.72%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	86.25%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.35%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.99%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.51%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.36%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.00%	97.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.92%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.80%	91.19%
CHEMBL299	P17252	Protein kinase C alpha	80.37%	98.03%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.11%	86.92%

Plants that contains it

• Centaurea glastifolia

Cross-Links

• PubChem: 15867701
• LOTUS: LTS0024085
• wikiData: Q105305347