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Uscharin

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID d99ea33d-dc33-4855-9b4d-45fb3880cb6c
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name (1S,3R,5S,7R,9S,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)spiro[4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-9,2'-5H-1,3-thiazole]-14-carbaldehyde
SMILES (Canonical) CC1CC2(C3(C(O1)OC4CC5CCC6C(C5(CC4O3)C=O)CCC7(C6(CCC7C8=CC(=O)OC8)O)C)O)N=CCS2
SMILES (Isomeric) C[C@@H]1C[C@]2([C@]3([C@@H](O1)O[C@@H]4C[C@@H]5CC[C@@H]6[C@@H]([C@]5(C[C@H]4O3)C=O)CC[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)O)N=CCS2
InChI InChI=1S/C31H41NO8S/c1-17-13-30(32-9-10-41-30)31(36)26(38-17)39-23-12-19-3-4-22-21(28(19,16-33)14-24(23)40-31)5-7-27(2)20(6-8-29(22,27)35)18-11-25(34)37-15-18/h9,11,16-17,19-24,26,35-36H,3-8,10,12-15H2,1-2H3/t17-,19+,20-,21+,22-,23-,24-,26+,27-,28-,29+,30+,31-/m1/s1
InChI Key DONIPVCAKBPJLH-IGACXKNBSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C31H41NO8S
Molecular Weight 587.70 g/mol
Exact Mass 587.25528844 g/mol
Topological Polar Surface Area (TPSA) 149.00 Ų
XlogP 1.40
Atomic LogP (AlogP) 3.15
H-Bond Acceptor 10
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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Uscharine
UNII-L7XQV67FTV
L7XQV67FTV
24211-81-2
14-Hydroxy-2,3-((6-hydroxy-9-methyl-8-oxa-1-thia-4-azaspiro(4.5)dec-3-ene-6,7-diyl)bis(oxy))-19-oxocard-20(22)-enolide (2alpha(5S,6R,7S,9R),3beta,5alpha)-
Uscharine (6CI)
USCHARIN [MI]
C31H41O8NS
CHEMBL500585
Card-20(22)-enolide, 14-hydroxy-2,3-((6-hydroxy-9-methyl-8-oxa-1-thia-4-azaspiro(4.5)dec-3-ene-6,7-diyl)bis(oxy))-19-oxo-, (2alpha(5S,6R,7S,9R),3beta,5alpha)-
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Uscharin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9131 91.31%
Caco-2 - 0.8301 83.01%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.6515 65.15%
OATP2B1 inhibitior - 0.5766 57.66%
OATP1B1 inhibitior + 0.8819 88.19%
OATP1B3 inhibitior + 0.9417 94.17%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7102 71.02%
BSEP inhibitior + 0.8938 89.38%
P-glycoprotein inhibitior + 0.6862 68.62%
P-glycoprotein substrate + 0.7427 74.27%
CYP3A4 substrate + 0.7211 72.11%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8876 88.76%
CYP3A4 inhibition - 0.8719 87.19%
CYP2C9 inhibition - 0.7973 79.73%
CYP2C19 inhibition - 0.6449 64.49%
CYP2D6 inhibition - 0.9065 90.65%
CYP1A2 inhibition - 0.7523 75.23%
CYP2C8 inhibition + 0.6176 61.76%
CYP inhibitory promiscuity - 0.8185 81.85%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4708 47.08%
Eye corrosion - 0.9842 98.42%
Eye irritation - 0.9407 94.07%
Skin irritation - 0.7207 72.07%
Skin corrosion - 0.9151 91.51%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7249 72.49%
Micronuclear + 0.5600 56.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.8163 81.63%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.5166 51.66%
Acute Oral Toxicity (c) III 0.5751 57.51%
Estrogen receptor binding + 0.7734 77.34%
Androgen receptor binding + 0.8057 80.57%
Thyroid receptor binding - 0.4928 49.28%
Glucocorticoid receptor binding + 0.6923 69.23%
Aromatase binding + 0.6522 65.22%
PPAR gamma + 0.5859 58.59%
Honey bee toxicity - 0.7374 73.74%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.6500 65.00%
Fish aquatic toxicity + 0.9620 96.20%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL2146346 P46531 Neurogenic locus notch homolog protein 1 400 nM
 IC50
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.86% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.10% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.89% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.85% 95.56%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 93.80% 93.40%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.79% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.41% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.11% 99.23%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 90.02% 96.77%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.28% 91.11%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.47% 95.89%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 86.49% 81.11%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 85.45% 92.86%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 85.35% 100.00%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 84.75% 83.57%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.63% 82.69%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.43% 97.25%
CHEMBL3714130 P46095 G-protein coupled receptor 6 84.33% 97.36%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 84.22% 86.00%
CHEMBL3038469 P24941 CDK2/Cyclin A 82.55% 91.38%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.11% 93.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.79% 97.33%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 81.22% 82.38%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 81.08% 98.99%
CHEMBL4208 P20618 Proteasome component C5 80.56% 90.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.34% 93.04%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Anemone narcissiflora
Asclepias curassavica
Calotropis procera
Gomphocarpus fruticosus
Gomphocarpus fruticosus subsp. fruticosus
Hyperbaena columbica
Viburnum lantanoides

Cross-Links

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PubChem 11261800
NPASS NPC163365
ChEMBL CHEMBL500585
LOTUS LTS0036534
wikiData Q27282814