[(1S,2R,5R,6R,7R,8R,11R)-6-(acetyloxymethyl)-5,7,11-trihydroxy-2,7-dimethyl-10-oxo-9-oxatricyclo[6.3.1.01,5]dodecan-6-yl]methyl butanoate

Details

• Internal ID: edc21c5d-613b-4c17-9376-2a4901d3e7d6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,2R,5R,6R,7R,8R,11R)-6-(acetyloxymethyl)-5,7,11-trihydroxy-2,7-dimethyl-10-oxo-9-oxatricyclo[6.3.1.01,5]dodecan-6-yl]methyl butanoate
• SMILES (Canonical): CCCC(=O)OCC1(C(C2CC3(C1(CCC3C)O)C(C(=O)O2)O)(C)O)COC(=O)C
• SMILES (Isomeric): CCCC(=O)OC[C@]1([C@@]([C@H]2C[C@@]3([C@@]1(CC[C@H]3C)O)[C@H](C(=O)O2)O)(C)O)COC(=O)C
• InChI: InChI=1S/C21H32O9/c1-5-6-15(23)29-11-19(10-28-13(3)22)18(4,26)14-9-20(16(24)17(25)30-14)12(2)7-8-21(19,20)27/h12,14,16,24,26-27H,5-11H2,1-4H3/t12-,14-,16+,18+,19+,20+,21+/m1/s1
• InChI Key: MIFYTBIFCJREKB-KVWQMUJTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₉
• Molecular Weight: 428.50 g/mol
• Exact Mass: 428.20463259 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.47
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8494	84.94%
Caco-2	-	0.6519	65.19%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7096	70.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8412	84.12%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5933	59.33%
P-glycoprotein inhibitior	-	0.5758	57.58%
P-glycoprotein substrate	+	0.5062	50.62%
CYP3A4 substrate	+	0.6781	67.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	-	0.7943	79.43%
CYP2C9 inhibition	-	0.8970	89.70%
CYP2C19 inhibition	-	0.8314	83.14%
CYP2D6 inhibition	-	0.9625	96.25%
CYP1A2 inhibition	-	0.9126	91.26%
CYP2C8 inhibition	-	0.6534	65.34%
CYP inhibitory promiscuity	-	0.9314	93.14%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7072	70.72%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8832	88.32%
Skin irritation	-	0.5861	58.61%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5351	53.51%
skin sensitisation	-	0.9528	95.28%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6645	66.45%
Acute Oral Toxicity (c)	I	0.3815	38.15%
Estrogen receptor binding	+	0.7927	79.27%
Androgen receptor binding	+	0.6510	65.10%
Thyroid receptor binding	-	0.5510	55.10%
Glucocorticoid receptor binding	+	0.6885	68.85%
Aromatase binding	+	0.5994	59.94%
PPAR gamma	+	0.5667	56.67%
Honey bee toxicity	-	0.8085	80.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9409	94.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.70%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.66%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	93.70%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.21%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.58%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	89.34%	90.17%
CHEMBL299	P17252	Protein kinase C alpha	89.01%	98.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.44%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.01%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.67%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.58%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	85.33%	92.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.76%	89.05%
CHEMBL2581	P07339	Cathepsin D	83.69%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.63%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.44%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.69%	95.56%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	82.29%	96.00%
CHEMBL1871	P10275	Androgen Receptor	82.12%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.07%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.00%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.64%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.39%	92.62%

Plants that contains it

• Illicium floridanum

Cross-Links

• PubChem: 163090240
• LOTUS: LTS0175518
• wikiData: Q105164663