(2S,3R,4S,5S)-2-[[(1S,2S,3S,4S,7S,9S,11S,12S,14S,17R,18R,19R,21R,22S)-2,11-dihydroxy-22-(2-hydroxypropan-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: ee1eb9f8-75e4-452a-b239-d184c670b847
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2S,3R,4S,5S)-2-[[(1S,2S,3S,4S,7S,9S,11S,12S,14S,17R,18R,19R,21R,22S)-2,11-dihydroxy-22-(2-hydroxypropan-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(CCC56CC57C(CCC6C4(C3O)C)C(C(CC7O)OC8C(C(C(CO8)O)O)O)(C)C)C)O2)C(C)(C)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@H](O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@]57[C@@H](CC[C@@H]6[C@@]4([C@@H]3O)C)C([C@H](C[C@@H]7O)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)(C)C)C)O2)C(C)(C)O
• InChI: InChI=1S/C35H56O10/c1-16-12-18-26(30(4,5)41)45-35(44-18)25(16)31(6)10-11-33-15-34(33)19(8-9-20(33)32(31,7)28(35)40)29(2,3)22(13-21(34)37)43-27-24(39)23(38)17(36)14-42-27/h16-28,36-41H,8-15H2,1-7H3/t16-,17+,18-,19+,20-,21+,22+,23+,24-,25-,26+,27+,28+,31-,32-,33+,34-,35+/m1/s1
• InChI Key: LMZFFAVUZOTJKB-PVRZAXBDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₆O₁₀
• Molecular Weight: 636.80 g/mol
• Exact Mass: 636.38734798 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7457	74.57%
Caco-2	-	0.8409	84.09%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6558	65.58%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.8718	87.18%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8726	87.26%
P-glycoprotein inhibitior	+	0.6785	67.85%
P-glycoprotein substrate	+	0.6253	62.53%
CYP3A4 substrate	+	0.7223	72.23%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8266	82.66%
CYP3A4 inhibition	-	0.9101	91.01%
CYP2C9 inhibition	-	0.8006	80.06%
CYP2C19 inhibition	-	0.8528	85.28%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.8578	85.78%
CYP2C8 inhibition	+	0.7619	76.19%
CYP inhibitory promiscuity	-	0.9581	95.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6248	62.48%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9181	91.81%
Skin irritation	-	0.6874	68.74%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7184	71.84%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6556	65.56%
skin sensitisation	-	0.8903	89.03%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7860	78.60%
Acute Oral Toxicity (c)	I	0.4592	45.92%
Estrogen receptor binding	-	0.4805	48.05%
Androgen receptor binding	+	0.7461	74.61%
Thyroid receptor binding	-	0.5368	53.68%
Glucocorticoid receptor binding	+	0.5545	55.45%
Aromatase binding	+	0.6654	66.54%
PPAR gamma	+	0.6263	62.63%
Honey bee toxicity	-	0.6553	65.53%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9120	91.20%

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	99.40%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.47%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.49%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.64%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.56%	92.94%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.08%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.08%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.76%	96.61%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	91.52%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.62%	97.14%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	88.67%	92.88%
CHEMBL259	P32245	Melanocortin receptor 4	88.41%	95.38%
CHEMBL1914	P06276	Butyrylcholinesterase	86.60%	95.00%
CHEMBL2996	Q05655	Protein kinase C delta	86.50%	97.79%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.34%	82.69%
CHEMBL2179	P04062	Beta-glucocerebrosidase	85.96%	85.31%
CHEMBL2581	P07339	Cathepsin D	85.68%	98.95%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.48%	95.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.47%	85.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.99%	97.33%
CHEMBL204	P00734	Thrombin	84.34%	96.01%
CHEMBL1871	P10275	Androgen Receptor	84.22%	96.43%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.17%	97.53%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.05%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.49%	93.04%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.12%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.82%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.64%	89.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.09%	92.86%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.07%	98.99%

Plants that contains it

• Actaea simplex

Cross-Links

• PubChem: 162897218
• LOTUS: LTS0019307
• wikiData: Q105154206