Moronic Acid
Basic information
- CAS
6713-27-5- Standard SMILES
CC1(C)C=C2[C@H]3CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O)CC1- InChIKey
UMYJVVZWBKIXQQ-QALSDZMNSA-N- Molecular formula
- C30H46O3
- Average molar mass
- 454.7 g/mol
- Monoisotopic mass
- 454.34469533
Overview
Moronic acid is a pentacyclic triterpenoid that is olean-18-ene substituted at position 3 by an oxo group and position 28 by a carboxy group. It has a role as a metabolite, an anti-HIV agent and an anti-HSV-1 agent. It derives from a hydride of an oleanane.
Names & identifiers
- Preferred name
- Moronic Acid
- IUPAC
- (4aS,6aR,6aR,6bR,8aR,12aR,14aS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-4,5,6,6a,7,8,8a,11,12,13,14,14a-dodecahydro-3H-picene-4a-carboxylic acid
- English name
- moronic acid
- Molecular formula
- C30H46O3
- Molecular weight
- 454.68
Names & synonyms
Moronic acid6713-27-53-Oxoolean-18-en-28-oic acid(4aS,6aR,6aR,6bR,8aR,12aR,14aS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-4,5,6,6a,7,8,8a,11,12,13,14,14a-dodecahydro-3H-picene-4a-carboxylic acidXW8W7HC4JKCHEBI:30815DTXSID30891948RefChem:159742DTXCID001031460(+)-MORONIC ACIDMLS000563430MFCD11113464
Show more names
moronicaci3-Oxooleana-18-ene-28-oic acidOlean-18-en-28-oic acid,3-oxo-3-Oxo-5α-olean-18-en-28-oic acid
MoronicacidSMR000232278(4aS,6aR,6bR,8aR,12aR,12bR,14aS)-2,2,6a,6b,9,9,12a-Heptamethyl-10-oxo-3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-octadecahydropicene-4a(2H)-carboxylic acidAMBRONIC ACIDUNII-XW8W7HC4JKMLS000728508SCHEMBL3249723-Oxoolean-18-en-28-oic acid; (+)-Moronic acid; Ambronic acid
Database identifiers
- CAS
6713-27-5
Properties
Computed structural properties
- XLogP
- 7.4
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 927
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Physicochemical properties
- Melting point
- 212 °C · 212 °C(dec.)
- Boiling point
- 550 · 550.0±50.0 °C(Predicted)
- Density
- 1.09 · 1.09±0.1 g/cm3(Predicted)
- solubility
- 1 · Chloroform: Sparingly soluble: 1-10 mg/mlMethanol: Slightly soluble: 0.1-1 mg/ml
- form
- Solid
- pka
- 4.59 · 4.59±0.70(Predicted)
- color
- White to off-white
- FDA UNII
- 8 W7HC4JK · XW8W7HC4JK
Chemistry & industry
Applications
UsesMoronic Acid and its derivatives can have antidiabetic activity by inhibiting PTP-1B. Moronic Acid is also shown sustained antidiabetic and antihyperglycemic action possibly mediated by an insulin sensitization in rat models.
General DescriptionMoronic acid is a fatty acid found in the seeds of Morus alba. It has been shown to have anti-infective properties by binding to the bacterial efflux protein, which is responsible for transporting toxic compounds out of the cell. The binding of moronic acid to the efflux protein prevents it from functioning and leads to increased expression of proinflammatory genes, ultimately leading to cell death. Moronic acid has also been shown to bind to a receptor on Staphylococcus aureus that is responsible for regulating virulence factors, leading to decreased production of proteins such as coagulase and proteases. Moronic acid also binds with oleanolic acid and inhibits the growth of Mycobacterium tuberculosis in vitro.
Additional notes
DefinitionChEBI: Moronic acid is a pentacyclic triterpenoid that is olean-18-ene substituted at position 3 by an oxo group and position 28 by a carboxy group. It has a role as a metabolite, an anti-HSV-1 agent and an anti-HIV agent. It derives from a hydride of an oleanane.
Related reactions
0 records
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Compound notes
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