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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-02-03 11:04:33 UTC
Update Date2020-02-26 21:35:34 UTC
HMDB IDHMDB0011659
Secondary Accession Numbers
  • HMDB11659
Metabolite Identification
Common Name2-Methylerythritol
Description2-C-methyl-D-erythritol is a soluble carbohydrate that is found in certain higher plants. In particular, it can be found in the petals, leaves and stems of certain flowering plants (PMID: 15384409 ). 2-Methylerythritol or 2-C-methyl-D-erythritol is likely a dephosphorylated form of 2-C-methyl-D-erythritol-4-phosphate. 2-C-methyl-D-erythritol-4-phosphate (MEP) is a central component to the non-mevalonate pathway for isoprenoid synthesis. This pathway is unique to certain gram negative and a few gram positive bacteria as well as plants and apicomplexan protozoa such as malaria parasites. Isoprenoid compounds are a diverse group of natural products that are essential components in all cells. Isoprenoids are biosynthesized from the simple precursors isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). IPP and DMAPP serve as the basis for the biosynthesis of molecules used in processes as diverse as protein prenylation, cell membrane maintenance, hormones, protein anchoring and N-glycosylation. 2-Methylerythritol is occasionally found in human urine specimens and is believed to be from exogenous dietary sources (plant products, leafy salads) or possibly produced by certain species of gut microflora.
Structure
Data?1582752934
Synonyms
ValueSource
(2R,3S)-2-Methyl-1,2,3,4-butanetetrolHMDB
2-C-Methyl-D-erythritolHMDB
2-C-MethylerythritolHMDB
3-MethylerythritolHMDB
[S-(R,S)]-2-Methyl-1,2,3,4-butanetetrolHMDB
3-C-MethylerythritolHMDB
2-MethylerythritolHMDB
Chemical FormulaC5H12O4
Average Molecular Weight136.1464
Monoisotopic Molecular Weight136.073558872
IUPAC Name(3S)-2-methylbutane-1,2,3,4-tetrol
Traditional Name(3S)-2-methylbutane-1,2,3,4-tetrol
CAS Registry Number93921-83-6
SMILES
CC(O)(CO)[C@@H](O)CO
InChI Identifier
InChI=1S/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m0/s1
InChI KeyHGVJFBSSLICXEM-CRCLSJGQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

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 Solubility742 g/LALOGPS
logP-1.8ALOGPS
logP-2.2ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)12.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.12 m³·mol⁻¹ChemAxon
Polarizability13.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01t9-9000000000-7e4e7672c11a6f38d58eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0abi-9256500000-4488acec35fa28a4729cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1900000000-3d4da02cca74e8661ce3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-9100000000-aa5dbc8bde3ddd8a8adaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-4ce1f0c31e904689acaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-059i-6900000000-840be55e94295c91bf51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-9300000000-4bca42c5d391d6238fd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-5973a28a3a5b3302b8d7Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified25.3 (17.0-49.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028350
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481015
PDB IDNot Available
ChEBI ID86367
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Enomoto H, Kohata K, Nakayama M, Yamaguchi Y, Ichimura K: 2-C-methyl-D-erythritol is a major carbohydrate in petals of Phlox subulata possibly involved in flower development. J Plant Physiol. 2004 Aug;161(8):977-80. [PubMed:15384409 ]