9,19-Cyclolanostan-28-oic acid, 1,3,16,20,24-pentahydroxy-24-(hydroxymethyl)-, beta-D-glucopyranosyl ester, (1alpha,3beta,4alpha,16beta,24S)-

Details

• Internal ID: 6fc8b1fe-417c-49ae-b5ed-20f4c917939a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,3S,4S,6S,7S,8R,11S,12S,14S,15R,16R)-15-[(2S,5S)-2,5-dihydroxy-5-(hydroxymethyl)-6-methylheptan-2-yl]-4,6,14-trihydroxy-7,12,16-trimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate
• InChI: InChI=1S/C37H62O13/c1-18(2)36(48,17-39)12-10-33(5,47)28-19(40)14-32(4)21-7-8-22-34(6,30(46)50-29-27(45)26(44)25(43)20(15-38)49-29)23(41)13-24(42)37(22)16-35(21,37)11-9-31(28,32)3/h18-29,38-45,47-48H,7-17H2,1-6H3/t19-,20+,21-,22-,23-,24-,25+,26-,27+,28-,29-,31+,32-,33-,34-,35-,36+,37+/m0/s1
• InChI Key: MOYBUGGNPKXCHY-DYDKOGDJSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₂O₁₃
• Molecular Weight: 714.90 g/mol
• Exact Mass: 714.41904203 g/mol
• Topological Polar Surface Area (TPSA): 238.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): -0.04
• H-Bond Acceptor: 13
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

• ((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) (1S,3S,4S,6S,7S,8R,11S,12S,14S,15R,16R)-15-((2S,5S)-2,5-dihydroxy-5-(hydroxymethyl)-6-methylheptan-2-yl)-4,6,14-trihydroxy-7,12,16-trimethylpentacyclo(9.7.0.01,3.03,8.012,16)octadecane-7-carboxylate
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,3S,4S,6S,7S,8R,11S,12S,14S,15R,16R)-15-[(2S,5S)-2,5-dihydroxy-5-(hydroxymethyl)-6-methylheptan-2-yl]-4,6,14-trihydroxy-7,12,16-trimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate
• RefChem:107579
• 9,19-Cyclolanostan-28-oic acid, 1,3,16,20,24-pentahydroxy-24-(hydroxymethyl)-, beta-D-glucopyranosyl ester, (1alpha,3beta,4alpha,16beta,24S)-
• DTXSID701103999
• 9,19-Cyclolanostan-28-oic acid, 1,3,16,20,24-pentahydroxy-24-(hydroxymethyl)-, I(2)-D-glucopyranosyl ester, (1I+/-,3I(2),4I+/-,16I(2),24S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6728	67.28%
Caco-2	-	0.8568	85.68%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7015	70.15%
OATP2B1 inhibitior	-	0.8641	86.41%
OATP1B1 inhibitior	+	0.8323	83.23%
OATP1B3 inhibitior	+	0.9131	91.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7764	77.64%
P-glycoprotein inhibitior	+	0.7309	73.09%
P-glycoprotein substrate	+	0.5493	54.93%
CYP3A4 substrate	+	0.7159	71.59%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8429	84.29%
CYP3A4 inhibition	-	0.8869	88.69%
CYP2C9 inhibition	-	0.7294	72.94%
CYP2C19 inhibition	-	0.8000	80.00%
CYP2D6 inhibition	-	0.9509	95.09%
CYP1A2 inhibition	-	0.8506	85.06%
CYP2C8 inhibition	+	0.6101	61.01%
CYP inhibitory promiscuity	-	0.9623	96.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7310	73.10%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9121	91.21%
Skin irritation	-	0.6940	69.40%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7013	70.13%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.9091	90.91%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8246	82.46%
Acute Oral Toxicity (c)	I	0.4565	45.65%
Estrogen receptor binding	+	0.6925	69.25%
Androgen receptor binding	+	0.7519	75.19%
Thyroid receptor binding	-	0.5488	54.88%
Glucocorticoid receptor binding	+	0.5890	58.90%
Aromatase binding	+	0.6408	64.08%
PPAR gamma	+	0.6582	65.82%
Honey bee toxicity	-	0.6090	60.90%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8751	87.51%

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	99.76%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.94%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.83%	96.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	97.25%	85.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.96%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.76%	96.95%
CHEMBL237	P41145	Kappa opioid receptor	94.84%	98.10%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.82%	85.14%
CHEMBL236	P41143	Delta opioid receptor	93.26%	99.35%
CHEMBL2581	P07339	Cathepsin D	92.99%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	92.29%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.93%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	91.35%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.64%	96.77%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.62%	98.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.08%	96.21%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	89.18%	95.71%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.76%	91.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.35%	96.47%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.94%	96.38%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.84%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.51%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.00%	97.14%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.60%	97.29%
CHEMBL220	P22303	Acetylcholinesterase	86.50%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.38%	89.34%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.26%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.32%	89.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.00%	95.71%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.93%	82.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.40%	94.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	83.71%	97.86%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.71%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.65%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.20%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.80%	92.50%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.70%	92.86%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.17%	93.04%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.13%	90.93%
CHEMBL340	P08684	Cytochrome P450 3A4	81.86%	91.19%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.34%	99.17%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.14%	90.08%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.12%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.46%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	80.33%	98.05%
CHEMBL1075317	P61964	WD repeat-containing protein 5	80.16%	96.33%

Plants that contains it

• Passiflora edulis

Cross-Links

• PubChem: 21609741
• LOTUS: LTS0009040
• wikiData: Q105169251