NAV

Ursolic acid

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Ursolic acid
DrugBank Accession Number
DB15588
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 456.711
Monoisotopic: 456.360345406
Chemical Formula
C30H48O3
Synonyms
  • Malol
  • Prunol
  • Urson
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGTPase HRas
regulator
Humans
UNeutrophil elastase
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
P3M2575F3F
CAS number
77-52-1
InChI Key
WCGUUGGRBIKTOS-GPOJBZKASA-N
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
IUPAC Name
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
SMILES
[H][C@@]12[C@@H](C)[C@H](C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0002395
KEGG Compound
C08988
ChemSpider
58472
BindingDB
50148911
RxNav
1426931
ChEBI
9908
ChEMBL
CHEMBL169
ZINC
ZINC000003978827
PDBe Ligand
6Q5
Wikipedia
Ursolic_acid
PDB Entries
5k3m / 5x8s

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentSyndrome, Metabolic1
2RecruitingSupportive CareLoss of muscle mass / Muscular Atrophy / Paraplegia / Quadriplegia / Resistance, Insulin / Spinal Cord Injuries1
1WithdrawnTreatmentPrimary Sclerosing Cholangitis (PSC)1
0CompletedBasic ScienceBioavailability of Phytonutrients1
0WithdrawnBasic ScienceProstate Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00059 mg/mLALOGPS
logP6.35ALOGPS
logP6.58Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.74Chemaxon
pKa (Strongest Basic)-0.84Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area57.53 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity133.7 m3·mol-1Chemaxon
Polarizability54.51 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0ue9-2941000000-2ca89e826b7fdd2c8c1c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002f-0023900000-43b07991e5cfcd6c9419
GC-MS Spectrum - GC-MSGC-MSsplash10-0ue9-2941000000-2ca89e826b7fdd2c8c1c
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0a4i-0000930000-25139768b4507e334b4a
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0a4i-0000900000-63b4335e8110c54aba6e
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-0a4i-0000900000-b6287e2cceb1071deab7
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0a4i-0000900000-27e80ae2f29ac7c2825c
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-0a4i-0000900000-433a030e07383bf9ecbf
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0000900000-315a19254ceeb5598e13
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0000900000-2eff827266b9664aa7cf
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0000900000-ff12fe00efc56275c007
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014l-0001223390-7f53534d3578e8cfc4b4
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0a4i-0000900000-63b4335e8110c54aba6e
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0a4i-0000900000-b6287e2cceb1071deab7
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0a4i-0000900000-27e80ae2f29ac7c2825c
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0a4i-0000900000-433a030e07383bf9ecbf
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01t9-0029800000-86a594c11680cf4a317f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0001211390-507a9b205eaa7310f0ec
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0037900000-08b9c68893f80ab994c8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0w9u-0001223691-a434f7aa9337860104e7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-052o-0960400000-41b5382473b677051164
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1951600000-bca0f48cca868f7d87b8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0021900000-d58366df105ed413ea57
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000900000-0ec4c5accdcd7280f663
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000900000-aab23c3caaf008ba7944
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0594500000-da0e4e5ab94ebccfca21
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-0000900000-028caf10b4ac823429ca
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0951000000-5eee1c352f4b3282caaf
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-218.935749
predicted
DarkChem Lite v0.1.0
[M-H]-218.596749
predicted
DarkChem Lite v0.1.0
[M-H]-213.45638
predicted
DeepCCS 1.0 (2019)
[M+H]+221.211649
predicted
DarkChem Lite v0.1.0
[M+H]+217.432749
predicted
DarkChem Lite v0.1.0
[M+H]+215.35179
predicted
DeepCCS 1.0 (2019)
[M+Na]+218.739149
predicted
DarkChem Lite v0.1.0
[M+Na]+217.108749
predicted
DarkChem Lite v0.1.0
[M+Na]+221.31422
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. GTPase HRas
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Protein c-terminus binding
Specific Function
Ras proteins bind GDP/GTP and possess intrinsic GTPase activity.
Gene Name
HRAS
Uniprot ID
P01112
Uniprot Name
GTPase HRas
Molecular Weight
21297.97 Da
References
  1. Bhaskar BV, Rammohan A, Babu TM, Zheng GY, Chen W, Rajendra W, Zyryanov GV, Gu W: Molecular insight into isoform specific inhibition of PI3K-alpha and PKC-eta with dietary agents through an ensemble pharmacophore and docking studies. Sci Rep. 2021 Jun 9;11(1):12150. doi: 10.1038/s41598-021-90287-3. [Article]
Details2. Neutrophil elastase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serine-type endopeptidase activity
Specific Function
Modifies the functions of natural killer cells, monocytes and granulocytes. Inhibits C5a-dependent neutrophil enzyme release and chemotaxis.
Gene Name
ELANE
Uniprot ID
P08246
Uniprot Name
Neutrophil elastase
Molecular Weight
28517.81 Da
References
  1. Mitaine-Offer AC, Hornebeck W, Sauvain M, Zeches-Hanrot M: Triterpenes and phytosterols as human leucocyte elastase inhibitors. Planta Med. 2002 Oct;68(10):930-2. doi: 10.1055/s-2002-34929. [Article]

Drug created at December 10, 2019 19:04 / Updated at June 27, 2022 23:48