Uzarine

Details

• Internal ID: 899dcf1a-752c-4ba4-90d0-0b6d323c80a0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O
• InChI: InChI=1S/C35H54O14/c1-33-8-5-18(47-32-30(43)28(41)26(39)23(49-32)15-46-31-29(42)27(40)25(38)22(13-36)48-31)12-17(33)3-4-21-20(33)6-9-34(2)19(7-10-35(21,34)44)16-11-24(37)45-14-16/h11,17-23,25-32,36,38-44H,3-10,12-15H2,1-2H3/t17-,18-,19+,20-,21+,22+,23+,25+,26+,27-,28-,29+,30+,31+,32+,33-,34+,35-/m0/s1
• InChI Key: COIUWGNHAYDCDZ-RHWYPIQRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₁₄
• Molecular Weight: 698.80 g/mol
• Exact Mass: 698.35135639 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.75
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• Uzarine
• EINECS 243-616-7
• Uzarigenin + 2-D-glucose [German]
• NSC 407809
• SCHEMBL702463
• CHEMBL2303618
• (3-beta,5-alpha)-3-[(2-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• (3beta,5alpha)-3-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• Card-20(22)-enolide, 3-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-14-hydroxy-, (3beta,5alpha)-
• Card-20(22)-enolide, 3-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-14-hydroxy-, (3.beta.,5.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8248	82.48%
Caco-2	-	0.8850	88.50%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8382	83.82%
OATP2B1 inhibitior	-	0.7381	73.81%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5069	50.69%
P-glycoprotein inhibitior	+	0.6658	66.58%
P-glycoprotein substrate	+	0.6279	62.79%
CYP3A4 substrate	+	0.7132	71.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9241	92.41%
CYP2C9 inhibition	-	0.9242	92.42%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6565	65.65%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9270	92.70%
Skin irritation	-	0.5648	56.48%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8321	83.21%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9189	91.89%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7229	72.29%
Acute Oral Toxicity (c)	I	0.8357	83.57%
Estrogen receptor binding	+	0.7945	79.45%
Androgen receptor binding	+	0.8123	81.23%
Thyroid receptor binding	-	0.6780	67.80%
Glucocorticoid receptor binding	+	0.5585	55.85%
Aromatase binding	+	0.6934	69.34%
PPAR gamma	+	0.6502	65.02%
Honey bee toxicity	-	0.6866	68.66%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9498	94.98%

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	98.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.48%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.16%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.59%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.31%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	90.88%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.16%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.88%	96.77%
CHEMBL1871	P10275	Androgen Receptor	87.56%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	87.56%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.54%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.16%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.88%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.78%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.61%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.92%	96.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.49%	85.14%
CHEMBL2581	P07339	Cathepsin D	84.76%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.81%	96.00%

Plants that contains it

• Asclepias eastwoodiana
• Asclepias tuberosa
• Calotropis procera
• Xysmalobium undulatum

Cross-Links

• PubChem: 20055063
• NPASS: NPC470897
• ChEMBL: CHEMBL2303618
• LOTUS: LTS0108364
• wikiData: Q104253155