methyl (1R,2R,3S,7S,8S,9S,10S,11S)-1-(chloromethyl)-2-hydroxy-8-[(Z)-2-(hydroxymethyl)but-2-enoyl]oxy-6-methylidene-9-(2-methylpropanoyloxy)-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradecane-10-carboxylate

Details

• Internal ID: 4e9c4f53-7807-463e-9e23-43033857ee88
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (1R,2R,3S,7S,8S,9S,10S,11S)-1-(chloromethyl)-2-hydroxy-8-[(Z)-2-(hydroxymethyl)but-2-enoyl]oxy-6-methylidene-9-(2-methylpropanoyloxy)-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradecane-10-carboxylate
• SMILES (Canonical): CC=C(CO)C(=O)OC1C2C(C(C3(CCC(O3)C(C1OC(=O)C(C)C)C(=O)OC)CCl)O)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(/CO)\C(=O)O[C@H]1[C@@H]2[C@@H]([C@H]([C@]3(CC[C@H](O3)[C@@H]([C@@H]1OC(=O)C(C)C)C(=O)OC)CCl)O)OC(=O)C2=C
• InChI: InChI=1S/C25H33ClO11/c1-6-13(9-27)23(31)35-17-15-12(4)22(30)36-19(15)20(28)25(10-26)8-7-14(37-25)16(24(32)33-5)18(17)34-21(29)11(2)3/h6,11,14-20,27-28H,4,7-10H2,1-3,5H3/b13-6-/t14-,15+,16-,17-,18-,19-,20+,25-/m0/s1
• InChI Key: ZDDAOLKNMGZIRJ-HYYNZVRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₃ClO₁₁
• Molecular Weight: 545.00 g/mol
• Exact Mass: 544.1711396 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9544	95.44%
Caco-2	-	0.7640	76.40%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7848	78.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8296	82.96%
OATP1B3 inhibitior	+	0.8975	89.75%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.6063	60.63%
P-glycoprotein inhibitior	+	0.7023	70.23%
P-glycoprotein substrate	+	0.6215	62.15%
CYP3A4 substrate	+	0.6972	69.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8934	89.34%
CYP3A4 inhibition	-	0.8865	88.65%
CYP2C9 inhibition	-	0.7846	78.46%
CYP2C19 inhibition	-	0.7977	79.77%
CYP2D6 inhibition	-	0.9142	91.42%
CYP1A2 inhibition	-	0.7903	79.03%
CYP2C8 inhibition	-	0.6065	60.65%
CYP inhibitory promiscuity	-	0.9195	91.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8244	82.44%
Carcinogenicity (trinary)	Danger	0.4513	45.13%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.9103	91.03%
Skin irritation	-	0.7010	70.10%
Skin corrosion	-	0.9272	92.72%
Ames mutagenesis	-	0.5570	55.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6354	63.54%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5979	59.79%
skin sensitisation	-	0.8472	84.72%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.8024	80.24%
Acute Oral Toxicity (c)	III	0.4907	49.07%
Estrogen receptor binding	+	0.7799	77.99%
Androgen receptor binding	+	0.6412	64.12%
Thyroid receptor binding	+	0.5404	54.04%
Glucocorticoid receptor binding	+	0.7147	71.47%
Aromatase binding	+	0.6004	60.04%
PPAR gamma	+	0.6664	66.64%
Honey bee toxicity	-	0.6158	61.58%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9503	95.03%

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	98.84%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.83%	91.11%
CHEMBL299	P17252	Protein kinase C alpha	96.64%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.15%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.22%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.44%	97.25%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.79%	92.62%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.69%	96.47%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.78%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.33%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.11%	97.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	88.47%	92.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.29%	95.89%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	88.01%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.25%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.98%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.88%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.92%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.49%	91.19%
CHEMBL5028	O14672	ADAM10	82.96%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.16%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.52%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.49%	96.61%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.24%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.10%	93.03%

Plants that contains it

• Tetragonotheca repanda

Cross-Links

• PubChem: 163106829
• LOTUS: LTS0005878
• wikiData: Q105372077