URSOLIC ACID

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Synonyms
UNII P3M2575F3F
Source Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...

Structure

InChI Key WCGUUGGRBIKTOS-GPOJBZKASA-N
Smiles C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(=O)O
InChI
InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C30H48O3
Molecular Weight 456.7
AlogP 6.49
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 57.53
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 33.0
Assay Description Organism Bioactivity Reference
Inhibition of alpha-glucosidase (unknown origin) using PNPG as substrate incubated for 15 min prior to substrate addition measured after 15 min by spectrophotometric analysis Homo sapiens 1780.0 nM
Antioxidant activity in high cholesterol diet fed Mus musculus KM (mouse) assessed as MDA level in liver at 150 mg/kg, ig for 10 days (Rvb = 13.6188 +/- 4.2522 nmol/ml) Mus musculus 7.33 nmol/ml
Antioxidant activity assessed as ferric ion reducing activity measured as trolox equivalents by FRAP assay None 13.58 umol/g
Antioxidant activity assessed as ABTS radical scavenging activity None None
Antioxidant activity assessed as DPPH radical scavenging activity after 30 min None None
Hypolipidemic activity in high cholesterol diet fed Mus musculus KM (mouse) assessed as total cholesterol level at 150 mg/kg, ig for 10 days (Rvb = 7.3219 +/- 1.00196 mmol/l) Mus musculus 5.22 mmol/L
Hypolipidemic activity in high cholesterol diet fed Mus musculus KM (mouse) assessed as triglyceride level at 150 mg/kg, ig for 10 days (Rvb = 0.9359 +/- 0.2817 mmol/l) Mus musculus 0.432 mmol/L
Hypolipidemic activity in high cholesterol diet fed Mus musculus KM (mouse) assessed as low density lipoprotein cholesterol at 150 mg/kg, ig for 10 days (Rvb = 4.2972 +/- 1.1725 mmol/l) Mus musculus 1.57 mmol/L
Hypolipidemic activity in high cholesterol diet fed Mus musculus KM (mouse) assessed as high density lipoprotein cholesterol at 150 mg/kg, ig for 10 days (Rvb = 2.6953+/- 0,58099 mmol/l) Mus musculus 2.44 mmol/L
Inhibition of PTP1B (unknown origin) Homo sapiens 3080.0 nM Inhibition of PTP1B (unknown origin) Homo sapiens 3080.0 nM
Growth inhibitory activity against po dosed fourth-instar larvae of Spodoptera frugiperda (fall armyworm) assessed as proportion of prothetely appearance of precocious pupal structure in larvae after 48 to 72 hr Spodoptera frugiperda 30.0 %
Growth inhibitory activity against po dosed Spodoptera frugiperda (fall armyworm) larvae assessed as promotion of apolysis to fifth instar with ecdysis inhibition at 5 to 20 ug/ml Spodoptera frugiperda None
Insecticidal activity against Drosophila melanogaster larvae fed with compound incorporated diet assessed as mortality after 72 hr by not choice test Drosophila melanogaster 41.3 ug.mL-1
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as relative growth index at 20 ug/ml (Rvb = 1.0 no_unit) Spodoptera frugiperda 0.29
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as relative growth index at 10 ug/ml (Rvb = 1.0 no_unit) Spodoptera frugiperda 0.73
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as relative growth index at 5 ug/ml (Rvb = 1.0 no_unit) Spodoptera frugiperda 0.98
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as growth index at 20 ug/ml (Rvb = 0.95 +/-0.02 no_unit) Spodoptera frugiperda 0.28
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as growth index at 10 ug/ml (Rvb = 0.95 +/-0.02 no_unit) Spodoptera frugiperda 0.69
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as growth index at 5 ug/ml (Rvb = 0.95 +/-0.02 no_unit) Spodoptera frugiperda 0.93
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as reduction in pupae weight at 25 ug/ml Spodoptera frugiperda None
Growth inhibitory activity against Spodoptera frugiperda (fall armyworm) larvae fed with compound containing diet assessed as delay in time to pupation at 20 ug/ml Spodoptera frugiperda 24.0 day
Insecticidal activity against Drosophila melanogaster larvae fed with compound incorporated diet assessed as mortality at 100 ug/ml after 72 hr by not choice test (Rvb = 0%) Drosophila melanogaster 100.0 %
Insecticidal activity against Drosophila melanogaster larvae fed with compound incorporated diet assessed as mortality at 50 ug/ml after 72 hr by not choice test (Rvb = 0%) Drosophila melanogaster 65.2 %
Insecticidal activity against Drosophila melanogaster larvae fed with compound incorporated diet assessed as mortality at 20 ug/ml after 72 hr by not choice test (Rvb = 0%) Drosophila melanogaster 15.1 %
Insecticidal activity against Drosophila melanogaster larvae fed with compound incorporated diet assessed as mortality at 10 ug/ml after 72 hr by not choice test (Rvb = 0%) Drosophila melanogaster 7.0 %
Acute toxicity against last larval stage of Spodoptera frugiperda (fall armyworm) assessed as mortality applied topically onto abdomen measured after 7 days Spodoptera frugiperda 10.2 ug ml-1
Acute toxicity against last larval stage of Spodoptera frugiperda (fall armyworm) assessed as survival at 50 ug/ml applied topically onto abdomen measured after 24 hr (Rvb = 98.8 +/-3.5%) Spodoptera frugiperda 0.0 %
Acute toxicity against last larval stage of Spodoptera frugiperda (fall armyworm) assessed as survival at 35 ug/ml applied topically onto abdomen measured after 24 hr (Rvb = 98.8 +/-3.5%) Spodoptera frugiperda 7.9 %
Acute toxicity against last larval stage of Spodoptera frugiperda (fall armyworm) assessed as survival at 20 ug/ml applied topically onto abdomen measured after 24 hr (Rvb = 98.8 +/-3.5%) Spodoptera frugiperda 20.1 %
Acute toxicity against last larval stage of Spodoptera frugiperda (fall armyworm) assessed as survival at 10 ug/ml applied topically onto abdomen measured after 24 hr (Rvb = 98.8 +/-3.5%) Spodoptera frugiperda 52.9 %
Acute toxicity against last larval stage of Spodoptera frugiperda (fall armyworm) assessed as survival at 5 ug/ml applied topically onto abdomen measured after 24 hr (Rvb = 98.8 +/-3.5%) Spodoptera frugiperda 73.0 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 40 ug/ml after 7 days Spodoptera frugiperda None
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 50 to 100 ug/ml after 7 days Spodoptera frugiperda 100.0 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 50 ug/ml after 21 days (Rvb = 5.6%) Spodoptera frugiperda 100.0 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 35 ug/ml after 21 days (Rvb = 5.6%) Spodoptera frugiperda 100.0 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 20 ug/ml after 21 days (Rvb = 5.6%) Spodoptera frugiperda 91.7 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 10 ug/ml after 21 days (Rvb = 5.6%) Spodoptera frugiperda 81.3 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 5 ug/ml after 21 days (Rvb = 5.6%) Spodoptera frugiperda 79.1 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 50 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 0.0 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 35 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 0.0 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 20 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 28.6 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 10 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 48.4 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 5 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 57.2 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 50 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 0.0 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 35 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 0.0 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 20 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 30.1 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 10 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 47.4 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 5 ug/ml after 21 days (Rvb = 100%) Spodoptera frugiperda 51.9 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 50 ug/ml after 7 days (Rvb = 5.6%) Spodoptera frugiperda 79.1 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 20 ug/ml after 7 days (Rvb = 5.6%) Spodoptera frugiperda 29.2 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 35 ug/ml after 7 days (Rvb = 5.6%) Spodoptera frugiperda 46.8 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 10 ug/ml after 7 days (Rvb = 5.6%) Spodoptera frugiperda 16.7 %
Insecticidal activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as mortality at 5 ug/ml after 7 days (Rvb = 5.6%) Spodoptera frugiperda 4.2 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 35 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 6.7 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 50 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 3.4 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 20 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 8.9 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 10 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 10.7 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as length gained at 5 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 68.6 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 50 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 32.5 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 35 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 49.2 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 20 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 52.5 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 10 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 53.3 %
Growth inhibitory activity against first-instar larval stage of Spodoptera frugiperda (fall armyworm) fed with compound incorporated diet assessed as weight gained at 5 ug/ml after 7 days (Rvb = 100%) Spodoptera frugiperda 81.5 %
Antifeedant activity against fourth-instar larval stage of Spodoptera litura reared on castor leaves assessed as decrease in food consumption at 150 ug/cm2 after 48 hr by no-choice leaf disk assay relative to untreated control Spodoptera litura 50.0 %
Antifeedant activity against fourth-instar larval stage of Spodoptera litura reared on castor leaves assessed as decrease in food consumption at 100 ug/cm2 after 48 hr by no-choice leaf disk assay relative to untreated control Spodoptera litura 40.0 %
Growth inhibition of Homo sapiens (human) THP1 cells at 10 uM after 48 hr by SRB assay Homo sapiens 52.0 %
Growth inhibition of Homo sapiens (human) PC3 cells at 10 uM after 48 hr by SRB assay Homo sapiens 60.0 %
Growth inhibition of Homo sapiens (human) IMR32 cells at 10 uM after 48 hr by SRB assay Homo sapiens 13.0 %
Growth inhibition of Homo sapiens (human) A549 cells at 10 uM after 48 hr by SRB assay Homo sapiens 8.0 %
Growth inhibition of Homo sapiens (human) SiHa cells at 10 uM after 48 hr by SRB assay Homo sapiens 67.0 %
Growth inhibition of Homo sapiens (human) HeLa cells at 10 uM after 48 hr by SRB assay Homo sapiens 65.0 %
Growth inhibition of Homo sapiens (human) SW620 cells at 10 uM after 48 hr by SRB assay Homo sapiens 71.0 %
Growth inhibition of Homo sapiens (human) COLO205 cells at 10 uM after 48 hr by SRB assay Homo sapiens 7.0 %
Cytotoxicity against Homo sapiens (human) MDA-MB-231 cells assessed as growth inhibition by MTT assay Homo sapiens 5.0 %
Inhibition of cathepsin D (unknown origin) using hemoglobin as substrate after 30 min by spectrophotometric analysis Homo sapiens 18200.0 nM
Toxicity in Swiss albino Mus musculus (mouse) assessed as mortality up to 100 mg/kg, po measured up to 72 hr Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as presence of secretions up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as diarrhea up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as convulsions up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as tremors up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as ataxia up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as lethargy up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as effect on mobility up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as abdominal constriction up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None
Toxicity in Swiss albino Mus musculus (mouse) assessed as weight loss up to 100 mg/kg, po measured up to 24 hr relative to control Mus musculus None

Cross References

Resources Reference
ChEMBL CHEMBL169
FDA SRS P3M2575F3F
PubChem 64945
SureChEMBL SCHEMBL70205
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