[(1R,2R,4S,5R,8R,10S,13S,14R,17S,18R,22S,23S)-10-[(3R,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-2,23-dihydroxy-4,5,9,9,14,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-22-yl] hexanoate

Details

• Internal ID: 0312c246-0891-483e-99af-d75c4c598781
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,2R,4S,5R,8R,10S,13S,14R,17S,18R,22S,23S)-10-[(3R,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-2,23-dihydroxy-4,5,9,9,14,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-22-yl] hexanoate
• SMILES (Canonical): CCCCCC(=O)OC1CC(CC2C13C(CC4(C2(CCC5(C4(CCC6C5CCC(C6(C)C)OC7COC(C(C7OC8C(C(C(C(O8)CO)O)O)O)O)OC9C(C(C(C(O9)CO)O)O)OC1C(C(C(CO1)O)O)O)C)C)OC3O)C)O)(C)C
• SMILES (Isomeric): CCCCCC(=O)O[C@H]1CC(C[C@@H]2[C@@]13[C@@H](C[C@@]4([C@@]2(CC[C@]5([C@]4(CC[C@@H]6[C@@H]5CC[C@@H](C6(C)C)O[C@@H]7CO[C@@H]([C@@H]([C@@H]7O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)C)C)O[C@@H]3O)C)O)(C)C
• InChI: InChI=1S/C58H96O24/c1-9-10-11-12-36(63)78-35-21-52(2,3)19-32-57-18-17-54(6)27-13-14-34(53(4,5)26(27)15-16-55(54,7)56(57,8)20-33(62)58(32,35)51(72)82-57)75-31-25-74-48(44(71)45(31)79-49-43(70)40(67)38(65)29(22-59)76-49)81-50-46(41(68)39(66)30(23-60)77-50)80-47-42(69)37(64)28(61)24-73-47/h26-35,37-51,59-62,64-72H,9-25H2,1-8H3/t26-,27+,28-,29-,30-,31-,32+,33-,34+,35+,37+,38-,39-,40+,41+,42-,43-,44-,45-,46-,47+,48-,49+,50+,51+,54-,55-,56+,57+,58-/m1/s1
• InChI Key: QKHRYXFNBBXWAG-BHTHGURZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₈H₉₆O₂₄
• Molecular Weight: 1177.40 g/mol
• Exact Mass: 1176.62915392 g/mol
• Topological Polar Surface Area (TPSA): 372.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): -0.65
• H-Bond Acceptor: 24
• H-Bond Donor: 13
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7694	76.94%
Caco-2	-	0.8750	87.50%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6743	67.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8062	80.62%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8648	86.48%
P-glycoprotein inhibitior	+	0.7468	74.68%
P-glycoprotein substrate	+	0.6897	68.97%
CYP3A4 substrate	+	0.7520	75.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8738	87.38%
CYP3A4 inhibition	-	0.8334	83.34%
CYP2C9 inhibition	-	0.8182	81.82%
CYP2C19 inhibition	-	0.8312	83.12%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9055	90.55%
CYP2C8 inhibition	+	0.7951	79.51%
CYP inhibitory promiscuity	-	0.9502	95.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6513	65.13%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8992	89.92%
Skin irritation	-	0.6627	66.27%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8063	80.63%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7084	70.84%
skin sensitisation	-	0.9199	91.99%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9165	91.65%
Acute Oral Toxicity (c)	I	0.4348	43.48%
Estrogen receptor binding	+	0.8021	80.21%
Androgen receptor binding	+	0.7603	76.03%
Thyroid receptor binding	+	0.5530	55.30%
Glucocorticoid receptor binding	+	0.7575	75.75%
Aromatase binding	+	0.6318	63.18%
PPAR gamma	+	0.8086	80.86%
Honey bee toxicity	-	0.6708	67.08%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6452	64.52%
Fish aquatic toxicity	+	0.9153	91.53%

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	98.18%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.66%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.01%	96.61%
CHEMBL221	P23219	Cyclooxygenase-1	96.80%	90.17%
CHEMBL5255	O00206	Toll-like receptor 4	95.98%	92.50%
CHEMBL4302	P08183	P-glycoprotein 1	95.12%	92.98%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	93.77%	92.86%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.51%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.33%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.70%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.53%	99.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	91.16%	100.00%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	90.96%	95.52%
CHEMBL2996	Q05655	Protein kinase C delta	90.19%	97.79%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.94%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.82%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.80%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.51%	97.09%
CHEMBL1871	P10275	Androgen Receptor	89.47%	96.43%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.31%	97.29%
CHEMBL299	P17252	Protein kinase C alpha	89.28%	98.03%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	89.02%	91.81%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.02%	82.50%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.95%	97.53%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.58%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.47%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.47%	96.21%
CHEMBL259	P32245	Melanocortin receptor 4	88.00%	95.38%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.23%	91.03%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.91%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.57%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.83%	95.89%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.70%	97.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.53%	95.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.89%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.68%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.68%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.76%	92.62%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	82.57%	95.36%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	81.99%	97.86%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.90%	89.05%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.65%	97.28%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.32%	85.83%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.91%	93.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.03%	95.83%

Plants that contains it

• Lysimachia capillipes

Cross-Links

• PubChem: 162912647
• LOTUS: LTS0136147
• wikiData: Q105223121