(8S,9R,10R,13R,14S,16R,17R)-17-[(2R,5R)-5-[[9-[(2S,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5R,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

Details

• Internal ID: d94d8f30-32b9-4fdb-8578-388e14944df7
• 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-[(2R,5R)-5-[[9-[(2S,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5R,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)CC(C(C)(C)O)NC6=C7C(=NC=N6)N(C=N7)C8C(C(C(O8)CO)O)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@H](C(C)(C)O)NC6=C7C(=NC=N6)N(C=N7)[C@@H]8[C@@H]([C@@H]([C@@H](O8)CO)O)O)O)O
• InChI: InChI=1S/C46H65N5O16/c1-41(2)19-9-10-25-43(5)13-21(54)35(44(43,6)14-28(56)45(25,7)20(19)11-22(36(41)62)66-40-34(61)32(59)30(57)24(16-53)67-40)46(8,64)27(55)12-26(42(3,4)63)50-37-29-38(48-17-47-37)51(18-49-29)39-33(60)31(58)23(15-52)65-39/h9,11,17-18,20-21,23-26,30-35,39-40,52-54,57-61,63-64H,10,12-16H2,1-8H3,(H,47,48,50)/t20-,21-,23+,24-,25+,26-,30+,31-,32+,33-,34-,35+,39+,40-,43+,44-,45+,46+/m1/s1
• InChI Key: URTOXXGIVHAQEK-HFWVBHEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₆₅N₅O₁₆
• Molecular Weight: 944.00 g/mol
• Exact Mass: 943.44263100 g/mol
• Topological Polar Surface Area (TPSA): 337.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.06
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9362	93.62%
Caco-2	-	0.8600	86.00%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Lysosomes	0.3404	34.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8447	84.47%
OATP1B3 inhibitior	+	0.9309	93.09%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8345	83.45%
P-glycoprotein inhibitior	+	0.7452	74.52%
P-glycoprotein substrate	+	0.6805	68.05%
CYP3A4 substrate	+	0.7317	73.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8214	82.14%
CYP2C19 inhibition	-	0.8191	81.91%
CYP2D6 inhibition	-	0.8942	89.42%
CYP1A2 inhibition	-	0.8177	81.77%
CYP2C8 inhibition	+	0.7467	74.67%
CYP inhibitory promiscuity	-	0.7656	76.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.4924	49.24%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.9000	90.00%
Skin irritation	-	0.7589	75.89%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6984	69.84%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5682	56.82%
skin sensitisation	-	0.8514	85.14%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6093	60.93%
Estrogen receptor binding	+	0.7171	71.71%
Androgen receptor binding	+	0.7649	76.49%
Thyroid receptor binding	+	0.6431	64.31%
Glucocorticoid receptor binding	+	0.7864	78.64%
Aromatase binding	+	0.6452	64.52%
PPAR gamma	+	0.8047	80.47%
Honey bee toxicity	-	0.6441	64.41%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9817	98.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.20%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.87%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.84%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.73%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.40%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.18%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.49%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.02%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	92.84%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	92.35%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.30%	96.61%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	90.32%	80.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.94%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.67%	95.56%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	87.90%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.83%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.04%	95.89%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.76%	97.53%
CHEMBL3589	P55263	Adenosine kinase	84.69%	98.05%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.83%	100.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.75%	97.86%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.23%	87.67%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.72%	94.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.59%	86.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.39%	82.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.15%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.09%	99.17%

Plants that contains it

• Cucurbita pepo

Cross-Links

• PubChem: 162933448
• LOTUS: LTS0035524
• wikiData: Q105278027