Showing metabocard for Azelaic acid (BMDB0000784)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:30 UTC
Update Date2020-05-11 22:28:50 UTC
BMDB IDBMDB0000784
Secondary Accession Numbers
  • BMDB00784
Metabolite Identification
Common NameAzelaic acid
DescriptionAzelaic acid, also known as 1,9-nonanedioate or azelex, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Azelaic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Azelaic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,7-DicarboxyheptaneChEBI
1,7-Heptanedicarboxylic acidChEBI
1,9-Nonanedioic acidChEBI
Acide azelaiqueChEBI
Acidum azelaicumChEBI
Anchoic acidChEBI
AzelainsaeureChEBI
AzelexChEBI
FinaceaChEBI
Lepargylic acidChEBI
N-Nonanedioic acidChEBI
NonandisaeureChEBI
SkinorenChEBI
Nonanedioic acidKegg
1,7-HeptanedicarboxylateGenerator
1,9-NonanedioateGenerator
AnchoateGenerator
LepargylateGenerator
N-NonanedioateGenerator
NonanedioateGenerator
AzelaateGenerator
Azalaic acidHMDB
AzelaicacidtechHMDB
Azelainic acidHMDB
AzelateHMDB
Emerox 1110HMDB
Emerox 1144HMDB
Emery'S L-110HMDB
FinevinHMDB
Heptanedicarboxylic acidHMDB
Nonanedioic acid azelaic acidHMDB
Nonanedioic acid homopolymerHMDB
Poly(azelaic anhydride)HMDB
Polyazelaic anhydrideHMDB
SkinoremHMDB
Azelaic acid, dilithium saltHMDB
Azelaic acid, dipotassium saltHMDB
Azelaic acid, disodium saltHMDB
Azelaic acid, monosodium saltHMDB
Azelaic acid, potassium saltHMDB
Azelaic acid, sodium saltHMDB
Monosodium azelateHMDB
Azelaic acidPhytoBank
Azelic acidPhytoBank
alpha,omega-Nonanedioic acidPhytoBank
α,ω-Nonanedioic acidPhytoBank
Chemical FormulaC9H16O4
Average Molecular Weight188.2209
Monoisotopic Molecular Weight188.104859
IUPAC Namenonanedioic acid
Traditional Nameazelaic acid
CAS Registry Number123-99-9
SMILES
OC(=O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChI KeyBDJRBEYXGGNYIS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point106.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.4 mg/mLNot Available
LogP1.57HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.37ALOGPS
logP1.82ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity46.54 m³·mol⁻¹ChemAxon
Polarizability20.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Epidermis
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000784
DrugBank IDDB00548
Phenol Explorer Compound IDNot Available
FooDB IDFDB012192
KNApSAcK IDC00045634
Chemspider ID2179
KEGG Compound IDC08261
BioCyc IDCPD0-1265
BiGG IDNot Available
Wikipedia LinkAzelaic_Acid
METLIN ID5750
PubChem Compound2266
PDB IDNot Available
ChEBI ID48131
References
Synthesis ReferenceChen, Song; Yan, Jinlong. Synthesis of azelaic acid by chemical oxidation with oleic acid. Pige Huagong (2003), 20(6), 31-35.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available