(2R,3R,4S,5S)-2-[[(1S,2R,3S,9S,17R,19R,22R)-2,16-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: bf39b35c-b721-4188-813f-7ebb5ce562ed
• 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)-2,16-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(C(CC56CC57CCC(C(C7CCC6C4(C3O)C)(C)C)OC8C(C(C(CO8)O)O)O)O)C)O2)C(C)(C)O
• SMILES (Isomeric): C[C@@H]1CC2[C@@H](O[C@]3(C1[C@]4(C(CC56CC57CC[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)O)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)32(7)21(37)13-34-15-33(34)11-10-22(43-27-24(39)23(38)17(36)14-42-27)29(2,3)19(33)8-9-20(34)31(32,6)28(35)40/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: JKPGINPCCVKTKQ-VJXPIYMOSA-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: 2.40
• 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	-	0.8451	84.51%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6558	65.58%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.8677	86.77%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8831	88.31%
P-glycoprotein inhibitior	+	0.6712	67.12%
P-glycoprotein substrate	+	0.5614	56.14%
CYP3A4 substrate	+	0.7205	72.05%
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	+	0.7479	74.79%
CYP inhibitory promiscuity	-	0.9581	95.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6248	62.48%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9174	91.74%
Skin irritation	-	0.6874	68.74%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6507	65.07%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6841	68.41%
skin sensitisation	-	0.8903	89.03%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7193	71.93%
Acute Oral Toxicity (c)	I	0.4592	45.92%
Estrogen receptor binding	-	0.4949	49.49%
Androgen receptor binding	+	0.7450	74.50%
Thyroid receptor binding	-	0.5440	54.40%
Glucocorticoid receptor binding	-	0.4659	46.59%
Aromatase binding	+	0.6581	65.81%
PPAR gamma	+	0.6447	64.47%
Honey bee toxicity	-	0.6554	65.54%
Biodegradation	-	0.6750	67.50%
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	98.67%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.13%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.24%	96.77%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.22%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.81%	97.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.84%	92.88%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.83%	96.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	90.82%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.78%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.06%	97.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.00%	96.61%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.27%	85.14%
CHEMBL259	P32245	Melanocortin receptor 4	87.18%	95.38%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.25%	92.86%
CHEMBL3837	P07711	Cathepsin L	86.14%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.56%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	84.51%	95.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.93%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.90%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.09%	97.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.99%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.95%	91.07%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.72%	95.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.47%	82.69%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.32%	85.31%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.18%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.73%	94.75%
CHEMBL1871	P10275	Androgen Receptor	80.51%	96.43%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.15%	92.62%

Plants that contains it

• Actaea cimicifuga
• Actaea dahurica

Cross-Links

• PubChem: 11856499
• NPASS: NPC289609