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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:33:31 UTC
Update Date2018-05-19 21:31:52 UTC
HMDB IDHMDB0004085
Secondary Accession Numbers
  • HMDB04085
Metabolite Identification
Common NameTuberculostearic acid
DescriptionTuberculostearic acid is the characteristic fatty acid of acid-fast bacteria of the order Actinomycetales. (PMID 3329256 ). Tuberculostearic acid (TBSA) is a mycobacterial cell wall constituent that is possible to measure in plasma samples of patients with active tuberculosis. (PMID 14723350 ). Detection of tuberculostearic acid in cerebrospinal fluid by use of gas chromatography-mass spectrometry has proven to be a very rapid, sensitive, and specific test for tuberculous meningitis. (PMID 8438134 ).
Structure
Thumb
Synonyms
ValueSource
10-Methyloctadecanoic acidChEBI
10-Methylstearic acidChEBI
10-MethyloctadecanoateGenerator
TuberculostearateGenerator
10-MethylstearateGenerator
10-Methyl-octadecanoateHMDB
10-Methyl-octadecanoic acidHMDB
L-(+)-Tuberculostearic acidHMDB
Chemical FormulaC19H38O2
Average Molecular Weight298.5038
Monoisotopic Molecular Weight298.28718046
IUPAC Name10-methyloctadecanoic acid
Traditional Nametuberculostearic acid
CAS Registry Number542-47-2
SMILES
CCCCCCCCC(C)CCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C19H38O2/c1-3-4-5-6-9-12-15-18(2)16-13-10-7-8-11-14-17-19(20)21/h18H,3-17H2,1-2H3,(H,20,21)
InChI KeyBEOUGZFCUMNGOU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Monocarboxylic 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.2e-05 g/LALOGPS
logP8.33ALOGPS
logP7.43ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity90.83 m³·mol⁻¹ChemAxon
Polarizability40.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9750000000-b70e654cc058a5620b04View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009l-9541000000-43b10427114989dc2285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-48bc35c4e94091b267bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uej-5690000000-bf34278d4e8686e14d6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9520000000-c74137e204a6abcbfe3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-593b8b182233ab92b298View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-1090000000-eb2b1b9d5efeddefa9a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-1d265edf2fb2723a153bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected but not Quantified Adult (>18 years old)Not SpecifiedMycobacterium tuberculosis details
Cerebrospinal Fluid (CSF)Detected but not Quantified Adult (>18 years old)Not SpecifiedTuberculous meningitis details
Associated Disorders and Diseases
Disease References
Mycobacterium tuberculosis
  1. Almenoff PL, Brooks JB, Johnson A, Lesser M: Differentiation of sarcoidosis from tuberculosis by use of electron capture gas-liquid chromatography. Lung. 1996;174(6):349-58. [PubMed:8887930 ]
Tuberculous meningitis
  1. French GL, Teoh R, Chan CY, Humphries MJ, Cheung SW, O'Mahony G: Diagnosis of tuberculous meningitis by detection of tuberculostearic acid in cerebrospinal fluid. Lancet. 1987 Jul 18;2(8551):117-9. [PubMed:2885596 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023306
KNApSAcK IDNot Available
Chemspider ID58549
KEGG Compound IDC16794
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTuberculostearic acid
METLIN ID4294
PubChem Compound65037
PDB IDNot Available
ChEBI ID68565
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Almenoff PL, Brooks JB, Johnson A, Lesser M: Differentiation of sarcoidosis from tuberculosis by use of electron capture gas-liquid chromatography. Lung. 1996;174(6):349-58. [PubMed:8887930 ]
  2. French GL, Teoh R, Chan CY, Humphries MJ, Cheung SW, O'Mahony G: Diagnosis of tuberculous meningitis by detection of tuberculostearic acid in cerebrospinal fluid. Lancet. 1987 Jul 18;2(8551):117-9. [PubMed:2885596 ]
  3. Muranishi H, Nakashima M, Tsunematsu H, Shigematsu N, Isobe R: [Rapid diagnosis of pulmonary tuberculosis by detection of tuberculostearic acid with gas chromatography/mass spectrometry]. Kekkaku. 1987 Dec;62(12):627-33. [PubMed:3329256 ]
  4. Traunmuller F, Zeitlinger MA, Stoiser B, Lagler H, Abdel Salam HA, Presterl E, Graninger W: Circulating tuberculostearic acid in tuberculosis patients. Scand J Infect Dis. 2003;35(11-12):790-3. [PubMed:14723350 ]
  5. Frei R: [Current methods in rapid diagnosis of tuberculosis]. Schweiz Med Wochenschr. 1993 Feb 6;123(5):147-52. [PubMed:8438134 ]