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Ursolic acid

CAT: 0804-HY-N0140-01Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0140-01Size:50 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.
CAS Number
77-52-1
Product Name Alternative
Prunol; Urson; Malol
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
Autophagy; Endogenous Metabolite
Type
Natural Products
Related Pathways
Autophagy; Metabolic Enzyme/Protease
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Ursolic-acid.html
Purity
99.02
Solubility
DMSO : 33.33 mg/mL (ultrasonic)
Smiles
CC1(C)[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H]
Molecular Formula
C30H48O3
Molecular Weight
456.70
Precautions
H302, H315, H319, H335
References & Citations
[1]Yie Y, et al. Ursolic acid inhibited growth of hepatocellular carcinoma HepG2 cells through AMPKα-mediated reduction of DNA methyltransferase 1. Mol Cell Biochem. 2014 Dec 30.|[2]Kim M, et al. The combination of ursolic acid and leucine potentiates the differentiation of C2C12 murine myoblasts through the mTOR signaling pathway. Int J Mol Med. 2015 Mar;35 (3) :755-62.|[3]Kim ES, et al. Ursolic acid inhibits the invasive phenotype of SNU-484 human gastric cancer cells. Oncol Lett. 2015 Feb;9 (2) :897-902.|[4]Li R, et al. Ursolic Acid Promotes Apoptosis of SGC-7901 Gastric Cancer Cells through ROCK/PTEN Mediated Mitochondrial Translocation of Cofilin-1. Asian Pac J Cancer Prev. 2014;15 (22) :9593-7.|[5]Hu Z, et al. Ursolic acid improves survival and attenuates lung injury in septic rats induced by cecal ligation and puncture. J Surg Res. 2014 Oct 22. pii: S0022-4804 (14) 00967-6.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

(+)-Ursolic Acid

Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a geroprotector and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an ursolate. It derives from a hydride of an ursane.

CAS Number77-52-1
PubChem CID64945
IUPAC Name(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Molecular FormulaC30H48O3
Molecular Weight456.7
XLogP7.3
Topological Polar Surface Area57.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Heavy Atom Count33
Formal Charge0
Complexity874
SMILES
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)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
InChIKey
WCGUUGGRBIKTOS-GPOJBZKASA-N
Chemical Structure
2D Structure
2D structure of (+)-Ursolic Acid
CAS: 77-52-1
CID: 64945
Formula: C30H48O3
MW: 456.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight456.7
XLogP37.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass456.36034539
Monoisotopic Mass456.36034539
Topological Polar Surface Area57.5 Ų
Heavy Atom Count33
Formal Charge0
Complexity874
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
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