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Ursolic acid acetate

CAT: 0804-HY-N2815-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2815-01Size:1 mg
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Description
Ursolic acid acetate (Acetylursolic acid) is a triterpenoid compound and an inhibitor of Plasmodium falciparum heat shock protein 90 (PfHsp90) with a KD of 8.16 μM. Ursolic acid acetate is cytotoxic to KB cells, with an IC50 value of 8.4 μM. Ursolic acid acetate can be used in tumor and antimalarial research[1][2][3].
CAS Number
7372-30-7
Product Name Alternative
Acetylursolic acid; 3-Acetylursolic acid
UNSPSC
12352211
Hazard Statement
H315, H319, H335
Target
HSP; Parasite
Type
Natural Products
Related Pathways
Anti-infection; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/ursolic-acid-acetate.html
Purity
98.0
Solubility
DMSO : 25 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
[H][C@]12C3=CC[C@]4([C@@](CC[C@]5(C(C)([C@H](CC[C@@]54C)OC(C)=O)C)[H])([C@@]3(CC[C@]1(CC[C@H]([C@@H]2C)C)C(O)=O)C)C)[H]
Molecular Formula
C32H50O4
Molecular Weight
498.74
Precautions
H315, H319, H335
References & Citations
[1]Chiang YM, et al. Cytotoxic triterpenes from the aerial roots of Ficus microcarpa. Phytochemistry. 2005 Feb;66 (4) :495-501.|[2]Nndwammbi AAT, et al. Ursolic acid acetate and iso-mukaadial acetate bind to Plasmodium falciparum Hsp90, abrogating its chaperone function in vitro. Naunyn Schmiedebergs Arch Pharmacol. 2024 Jul;397 (7) :5179-5192.|[3]Gnoatto S C B, et al. Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4- (3-aminopropyl) piperazinyl] propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Bioorganic & medicinal chemistry, 2008, 16 (2) : 771-782.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
HSP90; Plasmodium

Chemical Information

O-Acetylursolic Acid

Acetylursolic acid is a triterpenoid.

CAS Number7372-30-7
PubChem CID6475119
IUPAC Name(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetyloxy-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 FormulaC32H50O4
Molecular Weight498.7
XLogP7.9
Topological Polar Surface Area63.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Heavy Atom Count36
Formal Charge0
Complexity981
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)OC(=O)C)C)C)[C@@H]2[C@H]1C)C)C(=O)O
InChI
InChI=1S/C32H50O4/c1-19-11-16-32(27(34)35)18-17-30(7)22(26(32)20(19)2)9-10-24-29(6)14-13-25(36-21(3)33)28(4,5)23(29)12-15-31(24,30)8/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)/t19-,20+,23+,24-,25+,26+,29+,30-,31-,32+/m1/s1
InChIKey
PHFUCJXOLZAQNH-OTMOLZNZSA-N
Chemical Structure
2D Structure
2D structure of O-Acetylursolic Acid
CAS: 7372-30-7
CID: 6475119
Formula: C32H50O4
MW: 498.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight498.7
XLogP37.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass498.37091007
Monoisotopic Mass498.37091007
Topological Polar Surface Area63.6 Ų
Heavy Atom Count36
Formal Charge0
Complexity981
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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