Lotoside I

Details

• Internal ID: fa99fe54-4d72-408e-9d88-a54d0a98b56b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,2R,3R,4R,6R,7R,8S,9R,12R,13R,16S,18R)-16-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-1,2,7,13,17,17-hexamethyl-6-(3-methylbut-2-enyl)-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-3,4,7-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4(C5CCC6C7C(C(OC7(C(C6(C5(CCC4C3(C)C)C)C)O)O)CC=C(C)C)(C)O)C)CO)O)OC8C(C(C(C(O8)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H]7[C@@]([C@H](O[C@]7([C@@H]([C@]6([C@@]5(CC[C@H]4C3(C)C)C)C)O)O)CC=C(C)C)(C)O)C)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C48H80O19/c1-20(2)10-13-28-47(9,59)38-22-11-12-26-44(6)16-15-27(43(4,5)25(44)14-17-45(26,7)46(22,8)42(58)48(38,60)67-28)64-41-37(66-39-34(56)32(54)29(51)21(3)61-39)36(31(53)24(19-50)63-41)65-40-35(57)33(55)30(52)23(18-49)62-40/h10,21-42,49-60H,11-19H2,1-9H3/t21-,22+,23+,24+,25-,26+,27-,28+,29-,30+,31-,32+,33-,34+,35+,36-,37+,38-,39-,40-,41-,42+,44-,45+,46-,47-,48+/m0/s1
• InChI Key: YTOUOWGIWWJGTJ-MQDYDPNJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₀O₁₉
• Molecular Weight: 961.10 g/mol
• Exact Mass: 960.52938032 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): -0.69
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6915	69.15%
Caco-2	-	0.8891	88.91%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7917	79.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8238	82.38%
OATP1B3 inhibitior	+	0.8498	84.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7654	76.54%
P-glycoprotein inhibitior	+	0.7636	76.36%
P-glycoprotein substrate	-	0.5426	54.26%
CYP3A4 substrate	+	0.7362	73.62%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8441	84.41%
CYP3A4 inhibition	-	0.9458	94.58%
CYP2C9 inhibition	-	0.8562	85.62%
CYP2C19 inhibition	-	0.8858	88.58%
CYP2D6 inhibition	-	0.9272	92.72%
CYP1A2 inhibition	-	0.8798	87.98%
CYP2C8 inhibition	+	0.6943	69.43%
CYP inhibitory promiscuity	-	0.8626	86.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9044	90.44%
Skin irritation	-	0.6285	62.85%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7872	78.72%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.8281	82.81%
skin sensitisation	-	0.9034	90.34%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8904	89.04%
Acute Oral Toxicity (c)	I	0.4680	46.80%
Estrogen receptor binding	+	0.7762	77.62%
Androgen receptor binding	+	0.7434	74.34%
Thyroid receptor binding	-	0.5307	53.07%
Glucocorticoid receptor binding	+	0.6725	67.25%
Aromatase binding	+	0.6682	66.82%
PPAR gamma	+	0.7726	77.26%
Honey bee toxicity	-	0.5894	58.94%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9531	95.31%

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	98.65%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.74%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.00%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.67%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.81%	91.24%
CHEMBL1937	Q92769	Histone deacetylase 2	90.95%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.63%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.47%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.77%	86.33%
CHEMBL3589	P55263	Adenosine kinase	87.75%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.35%	97.09%
CHEMBL233	P35372	Mu opioid receptor	87.34%	97.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.01%	97.36%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	85.51%	95.36%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.03%	97.86%
CHEMBL4072	P07858	Cathepsin B	84.83%	93.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.11%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.09%	92.94%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.03%	95.58%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.96%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.53%	95.83%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	81.51%	97.31%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	81.42%	96.67%
CHEMBL325	Q13547	Histone deacetylase 1	81.09%	95.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.77%	92.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.62%	91.03%
CHEMBL237	P41145	Kappa opioid receptor	80.12%	98.10%
CHEMBL2581	P07339	Cathepsin D	80.01%	98.95%

Plants that contains it

• Ziziphus jujuba
• Ziziphus lotus

Cross-Links

• PubChem: 102066551
• NPASS: NPC217713
• LOTUS: LTS0121835
• wikiData: Q105361794