cucurbitacin I 2-O-beta-D-glucopyranoside

Details

• Internal ID: 941eb646-deda-4aca-ada0-131284cdeaa3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
• SMILES (Canonical): CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2C=C(C1=O)OC5C(C(C(C(O5)CO)O)O)O)C)C)C(C)(C(=O)C=CC(C)(C)O)O)O)C)C
• SMILES (Isomeric): C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)[C@](C)(C(=O)/C=C/C(C)(C)O)O)O
• InChI: InChI=1S/C36H52O12/c1-31(2,45)12-11-23(39)36(8,46)28-19(38)14-33(5)22-10-9-17-18(35(22,7)24(40)15-34(28,33)6)13-20(29(44)32(17,3)4)47-30-27(43)26(42)25(41)21(16-37)48-30/h9,11-13,18-19,21-22,25-28,30,37-38,41-43,45-46H,10,14-16H2,1-8H3/b12-11+/t18-,19-,21-,22+,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1
• InChI Key: LIIOJBIJVPGVGO-JZZAZZIQSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₂O₁₂
• Molecular Weight: 676.80 g/mol
• Exact Mass: 676.34587709 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.88
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• cucurbitacin I 2-O-beta-D-glucopyranoside
• CHEBI:68917
• 29803-94-9
• (8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
• Cucurbitacine-I-glucoside
• beta-Glucoside de LA cucurbitacine (I)
• Compound NP-002365
• 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 2-(beta-D-glucopyranosyloxy)-9-methyl-16,20,25-trihydroxy-
• CHEMBL1765380
• ACon1_002046
• AKOS040735120
• NCGC00179885-01
• NCGC00179885-03
• BRD-K10934705-001-01-9
• Q27137272
• (4R,9beta,16alpha,23E)-16,20,25-trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-2-yl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9049	90.49%
Caco-2	-	0.8492	84.92%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8255	82.55%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8345	83.45%
OATP1B3 inhibitior	+	0.8709	87.09%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6044	60.44%
P-glycoprotein inhibitior	+	0.7306	73.06%
P-glycoprotein substrate	-	0.5851	58.51%
CYP3A4 substrate	+	0.7103	71.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8893	88.93%
CYP3A4 inhibition	-	0.7781	77.81%
CYP2C9 inhibition	-	0.8433	84.33%
CYP2C19 inhibition	-	0.9144	91.44%
CYP2D6 inhibition	-	0.9454	94.54%
CYP1A2 inhibition	-	0.8551	85.51%
CYP2C8 inhibition	+	0.6609	66.09%
CYP inhibitory promiscuity	-	0.9191	91.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6753	67.53%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9122	91.22%
Skin irritation	-	0.5459	54.59%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3605	36.05%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.7120	71.20%
skin sensitisation	-	0.8945	89.45%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5129	51.29%
Acute Oral Toxicity (c)	III	0.6142	61.42%
Estrogen receptor binding	+	0.7355	73.55%
Androgen receptor binding	+	0.7408	74.08%
Thyroid receptor binding	+	0.5453	54.53%
Glucocorticoid receptor binding	+	0.7558	75.58%
Aromatase binding	+	0.6966	69.66%
PPAR gamma	+	0.6791	67.91%
Honey bee toxicity	-	0.6655	66.55%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9826	98.26%

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	99.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.65%	96.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	95.51%	87.67%
CHEMBL2581	P07339	Cathepsin D	95.46%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.90%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.42%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.98%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.96%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.03%	96.61%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.92%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	90.33%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.56%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.37%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.62%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.45%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.84%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.92%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.72%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.88%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.97%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.66%	82.38%

Plants that contains it

• Bryonia cretica
• Citrullus colocynthis
• Iberis amara

Cross-Links

• PubChem: 6441519
• LOTUS: LTS0138798
• wikiData: Q27137272