(2R,3R,4S,5S)-2-[[(1S,2R,3S,9S,17R,19R,22R)-2-hydroxy-22-(2-methoxypropan-2-yl)-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: 59c8dd00-58b3-41c1-842f-8833613997e4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4S,5S)-2-[[(1S,2R,3S,9S,17R,19R,22R)-2-hydroxy-22-(2-methoxypropan-2-yl)-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1CC2C(OC3(C1C4(CCC56CC57CCC(C(C7CCC6C4(C3O)C)(C)C)OC8C(C(C(CO8)O)O)O)C)O2)C(C)(C)OC
• SMILES (Isomeric): C[C@@H]1CC2[C@@H](O[C@]3(C1[C@]4(CCC56CC57CC[C@@H](C(C7CCC6[C@@]4([C@H]3O)C)(C)C)O[C@@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)C)O2)C(C)(C)OC
• InChI: InChI=1S/C36H58O9/c1-18-15-20-27(31(4,5)41-8)45-36(44-20)26(18)32(6)13-14-35-17-34(35)12-11-23(43-28-25(39)24(38)19(37)16-42-28)30(2,3)21(34)9-10-22(35)33(32,7)29(36)40/h18-29,37-40H,9-17H2,1-8H3/t18-,19+,20?,21?,22?,23+,24+,25-,26?,27-,28-,29-,32-,33-,34?,35?,36+/m1/s1
• InChI Key: LAOCOVISLMUJNC-KVTAVDFCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₉
• Molecular Weight: 634.80 g/mol
• Exact Mass: 634.40808342 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.78
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7281	72.81%
Caco-2	-	0.8281	82.81%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6277	62.77%
OATP2B1 inhibitior	-	0.7245	72.45%
OATP1B1 inhibitior	+	0.8616	86.16%
OATP1B3 inhibitior	+	0.9369	93.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8567	85.67%
P-glycoprotein inhibitior	+	0.7103	71.03%
P-glycoprotein substrate	+	0.5754	57.54%
CYP3A4 substrate	+	0.7187	71.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8204	82.04%
CYP3A4 inhibition	-	0.8931	89.31%
CYP2C9 inhibition	-	0.7889	78.89%
CYP2C19 inhibition	-	0.8419	84.19%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	-	0.8543	85.43%
CYP2C8 inhibition	+	0.7440	74.40%
CYP inhibitory promiscuity	-	0.9609	96.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6219	62.19%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9174	91.74%
Skin irritation	-	0.7118	71.18%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.5408	54.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.6668	66.68%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7341	73.41%
skin sensitisation	-	0.8854	88.54%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7509	75.09%
Acute Oral Toxicity (c)	I	0.4266	42.66%
Estrogen receptor binding	-	0.5303	53.03%
Androgen receptor binding	+	0.7518	75.18%
Thyroid receptor binding	-	0.5552	55.52%
Glucocorticoid receptor binding	+	0.5677	56.77%
Aromatase binding	+	0.6779	67.79%
PPAR gamma	+	0.6041	60.41%
Honey bee toxicity	-	0.6570	65.70%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.8425	84.25%

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	99.46%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.00%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.71%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.72%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.26%	96.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	93.17%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.43%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.14%	97.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.24%	96.61%
CHEMBL325	Q13547	Histone deacetylase 1	87.23%	95.92%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.05%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.35%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.33%	98.75%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	86.03%	98.99%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.51%	97.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.33%	91.03%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.25%	96.95%
CHEMBL1902	P62942	FK506-binding protein 1A	85.25%	97.05%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.20%	85.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.56%	91.07%
CHEMBL259	P32245	Melanocortin receptor 4	84.47%	95.38%
CHEMBL206	P03372	Estrogen receptor alpha	83.95%	97.64%
CHEMBL1937	Q92769	Histone deacetylase 2	83.77%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.50%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.26%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.53%	100.00%
CHEMBL1871	P10275	Androgen Receptor	82.47%	96.43%
CHEMBL1914	P06276	Butyrylcholinesterase	82.31%	95.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.42%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.08%	92.62%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.99%	89.34%
CHEMBL2581	P07339	Cathepsin D	80.92%	98.95%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.78%	95.71%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.69%	94.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.57%	95.56%

Plants that contains it

• Actaea simplex

Cross-Links

• PubChem: 11856241
• NPASS: NPC290951