(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(3R,6R)-2-hydroxy-2-methyl-6-[(3S,8R,9R,10S,13R,14S,17R)-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol

Details

• Internal ID: 172d9a58-1171-47de-a41e-1c4aad9a98dc
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(3R,6R)-2-hydroxy-2-methyl-6-[(3S,8R,9R,10S,13R,14S,17R)-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• SMILES (Canonical): CC(CCC(C(C)(C)O)OC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)C3CCC4(C3(CCC5(C4CC=C6C5CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)O)C)C)C
• SMILES (Isomeric): C[C@H](CC[C@H](C(C)(C)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)[C@H]3CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC=C6[C@H]5CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)C
• InChI: InChI=1S/C48H82O18/c1-22(9-13-31(45(4,5)60)66-43-40(59)37(56)34(53)28(64-43)21-61-41-38(57)35(54)32(51)26(19-49)62-41)23-15-16-48(8)29-12-10-24-25(46(29,6)17-18-47(23,48)7)11-14-30(44(24,2)3)65-42-39(58)36(55)33(52)27(20-50)63-42/h10,22-23,25-43,49-60H,9,11-21H2,1-8H3/t22-,23-,25-,26-,27-,28-,29-,30+,31-,32-,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,46+,47-,48+/m1/s1
• InChI Key: ACQZDPFYFKJNJQ-PCIVXFBTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₂O₁₈
• Molecular Weight: 947.20 g/mol
• Exact Mass: 946.55011576 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): -0.03
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 14

Synonyms

• CHEMBL227427

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7122	71.22%
Caco-2	-	0.8885	88.85%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8033	80.33%
OATP2B1 inhibitior	-	0.8779	87.79%
OATP1B1 inhibitior	+	0.8502	85.02%
OATP1B3 inhibitior	-	0.3092	30.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7435	74.35%
P-glycoprotein inhibitior	+	0.7530	75.30%
P-glycoprotein substrate	-	0.5149	51.49%
CYP3A4 substrate	+	0.7118	71.18%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9631	96.31%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.9059	90.59%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.8883	88.83%
CYP2C8 inhibition	+	0.6313	63.13%
CYP inhibitory promiscuity	-	0.9012	90.12%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6129	61.29%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9055	90.55%
Skin irritation	-	0.6298	62.98%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8433	84.33%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7152	71.52%
skin sensitisation	-	0.9020	90.20%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6952	69.52%
Acute Oral Toxicity (c)	III	0.6471	64.71%
Estrogen receptor binding	+	0.7990	79.90%
Androgen receptor binding	+	0.7444	74.44%
Thyroid receptor binding	-	0.5090	50.90%
Glucocorticoid receptor binding	+	0.7076	70.76%
Aromatase binding	+	0.6600	66.00%
PPAR gamma	+	0.7853	78.53%
Honey bee toxicity	-	0.7057	70.57%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9499	94.99%

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	99.32%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.33%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.96%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.58%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.66%	98.95%
CHEMBL1977	P11473	Vitamin D receptor	90.39%	99.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.24%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.25%	93.56%
CHEMBL2996	Q05655	Protein kinase C delta	87.97%	97.79%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.94%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.73%	94.45%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.72%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	86.59%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.93%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	84.99%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.82%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.96%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.91%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	83.88%	90.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.16%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.14%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.49%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.63%	89.00%
CHEMBL1871	P10275	Androgen Receptor	80.62%	96.43%

Plants that contains it

• Siraitia grosvenorii

Cross-Links

• PubChem: 17752184
• LOTUS: LTS0098079
• wikiData: Q104909242