Ursolic acid

Ursolic acid
Compound Structure:
Synonyms: Ursolic acid; 77-52-1 ;Prunol; Malol; Urson
Compound ID: NMPC-1587
PubChem ID:

64945
Molecular Formula: C30H48O3
Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O
InChIKey: WCGUUGGRBIKTOS-GPOJBZKASA-N
About the compound:

Ursolic acid is a pentacyclictriterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclictriterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane. Ursolic Acid is a pentacyclictriterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities.
Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

456.7 g/mol

XLogP3-AA

7.3

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

3

Rotatable Bond Count

1

Exact Mass

456.36034539 g/mol

Monoisotopic Mass

456.36034539 g/mol

Topological Polar Surface Area

57.5Ų

Heavy Atom Count

33

Formal Charge

0

Complexity

874

Isotope Atom Count

0

Defined Atom Stereocenter Count

10

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Large, lustrous prisms from absolute alcohol, fine hair-like needles from dilute alcohol

Melting Point

284 °C

Solubility 

One part dissolves in 88 parts methanol, 178 alcohol, (35 boiling alcohol), 140 ether, 388 chloroform, 1675 carbon disulfide. Moderately soluble in acetone. Soluble in hot glacial acetic acid and in 2% alcoholic NaOH. Insoluble in petroleum ether.

Source:PubChem
Source Species: Borreria verticillata.
Hoslundia opposita
Myrianthus arboreus
Stachytarpheta jamaicensis
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