[(3S,3aR,4R,6E,8R,10E,11aR)-4-acetyloxy-3-(chloromethyl)-3-hydroxy-6,10-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-8-yl] acetate

Details

• Internal ID: 97307bc6-a76a-4e2b-9434-851507c9615c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3S,3aR,4R,6E,8R,10E,11aR)-4-acetyloxy-3-(chloromethyl)-3-hydroxy-6,10-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-8-yl] acetate
• SMILES (Canonical): CC1=CC2C(C(CC(=CC(C1)OC(=O)C)C)OC(=O)C)C(C(=O)O2)(CCl)O
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@@H]([C@@H](C/C(=C/[C@@H](C1)OC(=O)C)/C)OC(=O)C)[C@](C(=O)O2)(CCl)O
• InChI: InChI=1S/C19H25ClO7/c1-10-5-14(25-12(3)21)6-11(2)8-16-17(15(7-10)26-13(4)22)19(24,9-20)18(23)27-16/h5,8,14-17,24H,6-7,9H2,1-4H3/b10-5+,11-8+/t14-,15+,16+,17+,19-/m0/s1
• InChI Key: AXEPFXQADBSHJP-BNIFGNDOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₅ClO₇
• Molecular Weight: 400.80 g/mol
• Exact Mass: 400.1288808 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9805	98.05%
Caco-2	-	0.5917	59.17%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6435	64.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8975	89.75%
OATP1B3 inhibitior	+	0.8661	86.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6347	63.47%
P-glycoprotein inhibitior	-	0.6016	60.16%
P-glycoprotein substrate	-	0.7421	74.21%
CYP3A4 substrate	+	0.6531	65.31%
CYP2C9 substrate	-	0.8202	82.02%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.6542	65.42%
CYP2C9 inhibition	-	0.8240	82.40%
CYP2C19 inhibition	-	0.7788	77.88%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	-	0.7305	73.05%
CYP2C8 inhibition	-	0.7692	76.92%
CYP inhibitory promiscuity	-	0.9027	90.27%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8344	83.44%
Carcinogenicity (trinary)	Non-required	0.4198	41.98%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.9228	92.28%
Skin irritation	-	0.5523	55.23%
Skin corrosion	-	0.9033	90.33%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7084	70.84%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6784	67.84%
skin sensitisation	-	0.7552	75.52%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7470	74.70%
Acute Oral Toxicity (c)	III	0.4981	49.81%
Estrogen receptor binding	-	0.5633	56.33%
Androgen receptor binding	-	0.4850	48.50%
Thyroid receptor binding	+	0.5377	53.77%
Glucocorticoid receptor binding	+	0.6121	61.21%
Aromatase binding	-	0.5347	53.47%
PPAR gamma	-	0.5414	54.14%
Honey bee toxicity	-	0.7960	79.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.9417	94.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.35%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.19%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.74%	96.95%
CHEMBL2581	P07339	Cathepsin D	89.86%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.53%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.08%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.36%	95.56%

Plants that contains it

• Eupatorium glehnii

Cross-Links

• PubChem: 163185112
• LOTUS: LTS0045877
• wikiData: Q104920494