tricolorin C

Details

• Internal ID: a007e64b-1ebb-40d4-8885-2706070c3448
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: [(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22S,23R,24R,26R)-4,5,23-trihydroxy-24-(hydroxymethyl)-6-methyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-26-yl]oxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (2R,3R)-3-hydroxy-2-methylbutanoate
• SMILES (Canonical): CCCCCC1CCCCCCCCCC(=O)OC2C(C(OC(C2OC3C(C(C(C(O3)C)OC(=O)C(C)C(C)O)OC4C(C(C(C(O4)C)O)O)O)OC(=O)C(C)CC)OC5C(C(C(OC5O1)C)O)O)CO)O
• SMILES (Isomeric): CCCCC[C@H]1CCCCCCCCCC(=O)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)OC(=O)[C@H](C)[C@@H](C)O)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)OC(=O)[C@@H](C)CC)O[C@@H]5[C@H]([C@H]([C@H](O[C@H]5O1)C)O)O)CO)O
• InChI: InChI=1S/C50H86O22/c1-9-11-17-20-30-21-18-15-13-12-14-16-19-22-32(53)67-40-35(56)31(23-51)66-50(70-41-37(58)34(55)28(7)63-48(41)65-30)43(40)72-49-44(69-45(60)24(3)10-2)42(71-47-38(59)36(57)33(54)27(6)62-47)39(29(8)64-49)68-46(61)25(4)26(5)52/h24-31,33-44,47-52,54-59H,9-23H2,1-8H3/t24-,25+,26+,27-,28+,29-,30-,31+,33-,34-,35+,36+,37-,38+,39-,40-,41+,42+,43+,44+,47-,48-,49-,50-/m0/s1
• InChI Key: FEAFVOWMUGCJPB-GLDZGXLHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₆O₂₂
• Molecular Weight: 1039.20 g/mol
• Exact Mass: 1038.56107437 g/mol
• Topological Polar Surface Area (TPSA): 315.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 22
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

• ((2S,3S,4R,5R,6S)-2-methyl-5-((2S)-2-methylbutanoyl)oxy-6-(((1S,3R,4S,5R,6R,8R,10S,22S,23R,24R,26R)-4,5,23-trihydroxy-24-(hydroxymethyl)-6-methyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo(20.3.1.03,8)hexacosan-26-yl)oxy)-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl) (2R,3R)-3-hydroxy-2-methylbutanoate
• [(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22S,23R,24R,26R)-4,5,23-trihydroxy-24-(hydroxymethyl)-6-methyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-26-yl]oxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (2R,3R)-3-hydroxy-2-methylbutanoate
• RefChem:191365
• CHEMBL505541

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5080	50.80%
Caco-2	-	0.8697	86.97%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8099	80.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8143	81.43%
OATP1B3 inhibitior	+	0.8454	84.54%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9111	91.11%
P-glycoprotein inhibitior	+	0.7132	71.32%
P-glycoprotein substrate	+	0.7008	70.08%
CYP3A4 substrate	+	0.7079	70.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	-	0.7455	74.55%
CYP2C9 inhibition	-	0.9177	91.77%
CYP2C19 inhibition	-	0.8573	85.73%
CYP2D6 inhibition	-	0.9474	94.74%
CYP1A2 inhibition	-	0.8774	87.74%
CYP2C8 inhibition	+	0.6806	68.06%
CYP inhibitory promiscuity	-	0.9770	97.70%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7571	75.71%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9046	90.46%
Skin irritation	-	0.7993	79.93%
Skin corrosion	-	0.9598	95.98%
Ames mutagenesis	-	0.7178	71.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.3613	36.13%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6235	62.35%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8114	81.14%
Acute Oral Toxicity (c)	III	0.6414	64.14%
Estrogen receptor binding	+	0.8222	82.22%
Androgen receptor binding	+	0.5997	59.97%
Thyroid receptor binding	-	0.5324	53.24%
Glucocorticoid receptor binding	+	0.6669	66.69%
Aromatase binding	+	0.6056	60.56%
PPAR gamma	+	0.6899	68.99%
Honey bee toxicity	-	0.7207	72.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5527	55.27%
Fish aquatic toxicity	+	0.9191	91.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.20%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.80%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.25%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.98%	91.11%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	93.86%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.45%	92.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.85%	93.56%
CHEMBL4072	P07858	Cathepsin B	91.56%	93.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.38%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.31%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.86%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	89.81%	92.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.84%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.82%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.47%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.32%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	87.04%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.92%	90.71%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.25%	92.88%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.93%	96.21%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	85.78%	90.24%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.87%	97.29%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.17%	83.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.55%	96.00%
CHEMBL2996	Q05655	Protein kinase C delta	83.40%	97.79%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.69%	98.75%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.29%	95.83%
CHEMBL2514	O95665	Neurotensin receptor 2	82.24%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.86%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	81.29%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.24%	95.56%
CHEMBL1968	P07099	Epoxide hydrolase 1	81.02%	98.57%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.99%	96.37%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.80%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.06%	96.38%

Plants that contains it

• Ipomoea tricolor

Cross-Links

• PubChem: 10819886
• LOTUS: LTS0035669
• wikiData: Q104993891