methyl (2R)-2-[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.02,11.05,10]heptadec-10-en-16-yl]-2-hydroxyacetate

Details

• Internal ID: df5f7120-5991-40ba-b435-442c54b56f44
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (2R)-2-[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.02,11.05,10]heptadec-10-en-16-yl]-2-hydroxyacetate
• SMILES (Canonical): CC1(C(C2CC3=C4CC(=O)OC(C4(CCC3C(C1C(C(=O)OC)O)(C2=O)C)C)C5=COC=C5)O)C
• SMILES (Isomeric): C[C@@]12CC[C@H]3C(=C1CC(=O)O[C@H]2C4=COC=C4)C[C@H]5[C@H](C([C@@H]([C@@]3(C5=O)C)[C@H](C(=O)OC)O)(C)C)O
• InChI: InChI=1S/C27H34O8/c1-25(2)20(19(29)24(32)33-5)27(4)16-6-8-26(3)17(14(16)10-15(21(25)30)22(27)31)11-18(28)35-23(26)13-7-9-34-12-13/h7,9,12,15-16,19-21,23,29-30H,6,8,10-11H2,1-5H3/t15-,16-,19+,20-,21+,23-,26+,27+/m0/s1
• InChI Key: CWIUUACMAKLANV-UFQDEJKPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₈
• Molecular Weight: 486.60 g/mol
• Exact Mass: 486.22536804 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 3.13
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	-	0.6946	69.46%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8324	83.24%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.7433	74.33%
OATP1B3 inhibitior	-	0.2167	21.67%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6532	65.32%
P-glycoprotein inhibitior	+	0.5846	58.46%
P-glycoprotein substrate	+	0.5207	52.07%
CYP3A4 substrate	+	0.6909	69.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8353	83.53%
CYP3A4 inhibition	+	0.6620	66.20%
CYP2C9 inhibition	-	0.7630	76.30%
CYP2C19 inhibition	-	0.8734	87.34%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	-	0.8013	80.13%
CYP2C8 inhibition	+	0.6147	61.47%
CYP inhibitory promiscuity	-	0.8452	84.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.4262	42.62%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9259	92.59%
Skin irritation	-	0.6466	64.66%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4559	45.59%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8481	84.81%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7357	73.57%
Acute Oral Toxicity (c)	I	0.7082	70.82%
Estrogen receptor binding	+	0.8022	80.22%
Androgen receptor binding	+	0.6910	69.10%
Thyroid receptor binding	+	0.5780	57.80%
Glucocorticoid receptor binding	+	0.8608	86.08%
Aromatase binding	+	0.7240	72.40%
PPAR gamma	+	0.7178	71.78%
Honey bee toxicity	-	0.7335	73.35%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9946	99.46%

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	98.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.42%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.89%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.68%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.25%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.11%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.59%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.48%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.56%	91.24%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.22%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.06%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.88%	94.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.27%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.35%	86.33%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.62%	98.75%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.29%	94.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.01%	82.69%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.76%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.34%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.31%	97.25%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.77%	92.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.29%	100.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.95%	91.38%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.94%	92.88%
CHEMBL255	P29275	Adenosine A2b receptor	81.43%	98.59%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.97%	97.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.69%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.08%	95.56%

Plants that contains it

• Bergia capensis
• Cedrela odorata
• Swietenia macrophylla
• Swietenia mahagoni

Cross-Links

• PubChem: 21636326
• LOTUS: LTS0263948
• wikiData: Q104971298