methyl (1beta,11beta,12alpha,15beta)-15-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicrasan-21-oate

Details

• Internal ID: 1ce96a0d-044a-4683-a735-556aa95404cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9R,12S,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate
• SMILES (Canonical): CC1CC(=O)C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(OC5)C(=O)OC)O)O)C)O
• SMILES (Isomeric): C[C@@H]1CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C28H38O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h8,11,13-14,16,18-23,31-33H,7,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21-,22-,23+,26+,27-,28+/m1/s1
• InChI Key: SXRILXHNZYONKW-XZXXSJTKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₁
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.24141202 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Q27133976
• methyl (1beta,11beta,12alpha,15beta)-15-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicrasan-21-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9422	94.22%
Caco-2	-	0.7960	79.60%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7866	78.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8609	86.09%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8430	84.30%
P-glycoprotein inhibitior	+	0.7085	70.85%
P-glycoprotein substrate	+	0.8520	85.20%
CYP3A4 substrate	+	0.7098	70.98%
CYP2C9 substrate	-	0.8253	82.53%
CYP2D6 substrate	-	0.8954	89.54%
CYP3A4 inhibition	-	0.7186	71.86%
CYP2C9 inhibition	-	0.7836	78.36%
CYP2C19 inhibition	-	0.8348	83.48%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8286	82.86%
CYP2C8 inhibition	+	0.5054	50.54%
CYP inhibitory promiscuity	-	0.9045	90.45%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5305	53.05%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9250	92.50%
Skin irritation	-	0.6577	65.77%
Skin corrosion	-	0.9286	92.86%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6339	63.39%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5318	53.18%
Acute Oral Toxicity (c)	III	0.5975	59.75%
Estrogen receptor binding	+	0.7922	79.22%
Androgen receptor binding	+	0.7078	70.78%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7637	76.37%
Aromatase binding	+	0.7111	71.11%
PPAR gamma	+	0.6812	68.12%
Honey bee toxicity	-	0.5140	51.40%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9813	98.13%

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	99.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	97.17%	95.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.06%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.09%	96.00%
CHEMBL2581	P07339	Cathepsin D	94.82%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.06%	96.77%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.14%	89.34%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.13%	96.47%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.81%	98.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.75%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.31%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.79%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.45%	95.56%
CHEMBL3837	P07711	Cathepsin L	86.71%	96.61%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.43%	94.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.03%	89.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.87%	89.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.23%	92.88%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.83%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	83.76%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.54%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.19%	97.14%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.05%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.71%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.50%	100.00%
CHEMBL3776	Q14790	Caspase-8	82.11%	97.06%
CHEMBL2535	P11166	Glucose transporter	81.69%	98.75%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.44%	95.71%
CHEMBL325	Q13547	Histone deacetylase 1	81.40%	95.92%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.35%	97.47%
CHEMBL1937	Q92769	Histone deacetylase 2	81.09%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.74%	95.89%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 91666325
• LOTUS: LTS0105526
• wikiData: Q27133976