[(2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9-[(2R,3R,4R,5R,6S)-3-acetyloxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-4,5-dihydroxyoxan-3-yl] acetate

Details

• Internal ID: e753d27c-0f73-44de-bd43-e25ab3996473
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9-[(2R,3R,4R,5R,6S)-3-acetyloxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-4,5-dihydroxyoxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CC3C4(CC(C(C4(CCC35CC56C2C(C(CC6)OC7C(C(C(CO7)O)O)OC(=O)C)(C)C)C)C8(CCC(O8)C(C)(C)O)C)O)C)OC(=O)C)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]3[C@@]4(C[C@@H]([C@@H]([C@]4(CC[C@]35C[C@]56[C@@H]2C([C@H](CC6)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)OC(=O)C)(C)C)C)[C@]8(CC[C@H](O8)C(C)(C)O)C)O)C)OC(=O)C)O)O
• InChI: InChI=1S/C45H72O15/c1-21-30(50)32(52)34(57-23(3)47)38(55-21)58-26-17-27-42(9)18-24(48)35(43(10)13-11-29(60-43)40(6,7)53)41(42,8)15-16-44(27)20-45(44)14-12-28(39(4,5)36(26)45)59-37-33(56-22(2)46)31(51)25(49)19-54-37/h21,24-38,48-53H,11-20H2,1-10H3/t21-,24-,25+,26-,27-,28-,29-,30-,31-,32+,33+,34+,35-,36-,37-,38-,41+,42-,43+,44-,45+/m0/s1
• InChI Key: UAZCIPVWBFFESL-ADDKURDRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₂O₁₅
• Molecular Weight: 853.00 g/mol
• Exact Mass: 852.48712159 g/mol
• Topological Polar Surface Area (TPSA): 220.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9112	91.12%
Caco-2	-	0.8748	87.48%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8424	84.24%
OATP2B1 inhibitior	-	0.8754	87.54%
OATP1B1 inhibitior	+	0.8324	83.24%
OATP1B3 inhibitior	+	0.8915	89.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8787	87.87%
BSEP inhibitior	+	0.6616	66.16%
P-glycoprotein inhibitior	+	0.7749	77.49%
P-glycoprotein substrate	+	0.6292	62.92%
CYP3A4 substrate	+	0.7421	74.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.7257	72.57%
CYP2C9 inhibition	-	0.7889	78.89%
CYP2C19 inhibition	-	0.8603	86.03%
CYP2D6 inhibition	-	0.9530	95.30%
CYP1A2 inhibition	-	0.8768	87.68%
CYP2C8 inhibition	+	0.6903	69.03%
CYP inhibitory promiscuity	-	0.9724	97.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6001	60.01%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9058	90.58%
Skin irritation	-	0.6715	67.15%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7024	70.24%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6414	64.14%
skin sensitisation	-	0.9032	90.32%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.9639	96.39%
Acute Oral Toxicity (c)	I	0.5691	56.91%
Estrogen receptor binding	+	0.6721	67.21%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	-	0.5771	57.71%
Glucocorticoid receptor binding	+	0.7583	75.83%
Aromatase binding	+	0.6894	68.94%
PPAR gamma	+	0.7791	77.91%
Honey bee toxicity	-	0.6014	60.14%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9711	97.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.13%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.49%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.41%	96.77%
CHEMBL284	P27487	Dipeptidyl peptidase IV	94.57%	95.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.44%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.27%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.25%	89.00%
CHEMBL204	P00734	Thrombin	92.10%	96.01%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.63%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	91.18%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.18%	96.95%
CHEMBL1914	P06276	Butyrylcholinesterase	90.79%	95.00%
CHEMBL259	P32245	Melanocortin receptor 4	87.65%	95.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.56%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.46%	91.07%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	87.24%	97.31%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.09%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.82%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	85.06%	85.31%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.91%	83.57%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.45%	89.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.25%	92.88%
CHEMBL2581	P07339	Cathepsin D	82.98%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.79%	97.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.33%	97.36%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.75%	97.21%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.58%	95.71%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.18%	95.58%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.05%	85.30%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.73%	91.24%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.39%	100.00%

Plants that contains it

• Astragalus coluteocarpus

Cross-Links

• PubChem: 21633227
• LOTUS: LTS0009302
• wikiData: Q105269139