Showing Compound Card for Methyl acetylsalicylate (CDB000634)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 5 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:47:50 UTC
Updated at2020-12-07 19:07:36 UTC
CannabisDB IDCDB000634
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethyl acetylsalicylate
DescriptionMethyl acetylsalicylate also known as methyl aspirin, belongs to the class of organic compounds known as acylsalicylic acids and derivatives. These are salicylic acids or derivatives, that are O-acylated. Methyl acetylsalicylate is a methylated derivative of Aspirin. Aspirin or acetylsalicylic acid (ASA) is a commonly used drug for the treatment or prevention of pain, fever, inflammation and platelet aggregation and blood cloth formation. Acetylsalicylic acid accomplishes all these effect by irreversibly inhibiting the enzymes COX-1 and COX-2, preventing the formation of prostaglandines and tromboxanes (PMID: 14592543 ). In plants, salicylic acid and its derivatives are the key signaling molecule for the activation of the defense response known as the “Systemic Aquired Resistance” (SAR), which initiates in the plant tissue attacked by a biological aggressor. This signal is transmitted throughout the plant individual and also to neighbouring plants (by means of the volatile methyl salicylate) to prepare unexposed tissue for the impending attack (PMID: 15283665 ). Methyl salicylate has been reported to be a volatile component in cannabis samples (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Methyl 2-(acetyloxy)benzoic acidGenerator
2-Acetoxy-benzoic acid methyl esterChEMBL
2-Acetoxy-benzoate methyl esterGenerator
Methyl 2-acetoxybenzoic acidGenerator
Methyl aspirinMeSH
Acetylsalicylic acid methyl esterMeSH
Methyl acetylsalicylic acidMeSH
Chemical FormulaC10H10O4
Average Molecular Weight194.19
Monoisotopic Molecular Weight194.0579
IUPAC Namemethyl 2-(acetyloxy)benzoate
Traditional Namemethyl 2-(acetyloxy)benzoate
CAS Registry Number580-02-9
SMILES
COC(=O)C1=CC=CC=C1OC(C)=O
InChI Identifier
InChI=1S/C10H10O4/c1-7(11)14-9-6-4-3-5-8(9)10(12)13-2/h3-6H,1-2H3
InChI KeyONWPLBKWMAUFGZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylsalicylic acids and derivatives. These are salicylic acids or derivatives, that are O-acylated.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylsalicylic acids and derivatives
Alternative Parents
Substituents
  • Acylsalicylic acid or derivatives
  • Phenol ester
  • Benzoate ester
  • Phenoxy compound
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.52ALOGPS
logP1.58ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.22 m³·mol⁻¹ChemAxon
Polarizability19.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMethyl acetylsalicylate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. doi: 10.1016/s0049-3848(03)00379-7. [PubMed:14592543 ]
  2. Durrant WE, Dong X: Systemic acquired resistance. Annu Rev Phytopathol. 2004;42:185-209. doi: 10.1146/annurev.phyto.42.040803.140421. [PubMed:15283665 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details
1. Prostaglandin G/H synthase 2
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
Enzyme Details
2. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82