(+)-Marmasmic acid
Basic information
- CAS
2212-99-9- Standard SMILES
CC1(C)C[C@H]2C=C(C=O)[C@]34C[C@]3(C(=O)OC4O)[C@H]2C1- InChIKey
BIUVCPLWWOLECJ-LIHVSQBMSA-N- Molecular formula
- C15H18O4
- Average molar mass
- 262.3 g/mol
- Monoisotopic mass
- 262.12050905
Overview
Marasmic acid is a delta-lactone.
Names & identifiers
- Preferred name
- (+)-Marmasmic acid
- IUPAC
- (1S,2S,6S,9R)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo[7.3.1.01,9.02,6]tridec-7-ene-8-carbaldehyde
- English name
- marasmic acid
- Molecular formula
- C15H18O4
- Molecular weight
- 262.3
Names & synonyms
(+)-Marmasmic acidNSC318506CHEBI:6692CHEMBL1986451DTXSID70944765LMPR0103620002NCI60_002734C09701Q27107298(3aR,5aS,8aS,8bS)-3-Hydroxy-7,7-dimethyl-1-oxo-6,7,8,8a-tetrahydro-1H,3H,5aH-3a,8b-methanoindeno[4,5-c]furan-4-carbaldehyde3-Hydroxy-7,7-dimethyl-1-oxo-6,7,8,8a-tetrahydro-1H,3H,5aH-3a,8b-methanoindeno[4,5-c]furan-4-carbaldehyde3H,8b-Methano-1H-indeno[4,5-c]furan-4-carboxaldehyde, 5a,7,8,8a-tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo-
Show more names
CCRIS 1701NSC 318506NSC-318506marasmic acidLACHNELLA FUNGUS3H,6H-3a,8b-Methano-1H-indeno[4,5-c]furan-4-carboxaldehyde, 5a,7,8,8a-tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo-, (3S,3aR,5aS,8aS,8bS)-
Database identifiers
- CAS
2212-99-9- PubChem CID
- 330358
- DTXSID
DTXSID70944765- ChEMBL
CHEMBL1986451- ChEBI
CHEBI:6692
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 534
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
Physicochemical properties
- Melting point
- 173.5 °C · 173.5°C
- Boiling point
- 339.23 °C · 339.23°C (rough estimate)
- Density
- 1.0721 · 1.0721 (rough estimate)
- refractive index
- 1.435 · 1.4350 (estimate)
- pka
- 11.22 · 11.22±0.60(Predicted)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 74 EQ59M5C · S74EQ59M5C
Chemistry & industry
Applications
UsesMarasmic acid is a sesquiterpenoid with unsaturated dialdehyde functionality, first isolated from the Basidiomycete Marasmus conigenus. Marasmic acid has antibacterial, antifungal, cytotoxic and mutagenic activities, and its broad-spectrum activity is related to the α,β-unsaturated aldehyde group. However, its detailed biological mechanism of action has not been clarified. Previous studies have suggested that marasmic acid may exert its effects by reacting with endogenous nucleophiles or forming pyrrole derivatives. This study found that marasmic acid interferes with the membrane sensor histidine kinase MoSln1p of M. oryzae, superactivates the HOG pathway and causes cell death, indicating that its mechanism of action is different from other unsaturated dialdehyde sesquiterpenoids.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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