Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-02-03 11:04:33 UTC

Update Date

2022-03-07 02:51:12 UTC

HMDB ID

HMDB0011659

Secondary Accession Numbers

HMDB11659

Metabolite Identification

Common Name

2-Methylerythritol

Description

2-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R,3S)-2-Methyl-1,2,3,4-butanetetrol	HMDB
2-C-Methyl-D-erythritol	HMDB
2-C-Methylerythritol	HMDB
3-Methylerythritol	HMDB
[S-(R,S)]-2-Methyl-1,2,3,4-butanetetrol	HMDB
3-C-Methylerythritol	MeSH, HMDB
2-Methylerythritol	MeSH, HMDB

Chemical Formula

C₅H₁₂O₄

Average Molecular Weight

136.1464

Monoisotopic Molecular Weight

136.073558872

IUPAC Name

(3S)-2-methylbutane-1,2,3,4-tetrol

Traditional Name

(3S)-2-methylbutane-1,2,3,4-tetrol

CAS Registry Number

93921-83-6

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 Key

HGVJFBSSLICXEM-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetritol (CHEBI:86367 )

Ontology

Not Available

Urine (PMID: 24023812)

Source

Endogenous

Endogenous (HMDB: HMDB0011659)

Microbe

Microbe (HMDB: HMDB0011659)

Exogenous

Exogenous (HMDB: HMDB0011659)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	742 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.2	ChemAxon
logS	0.74	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.12 m³·mol⁻¹	ChemAxon
Polarizability	13.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.388	31661259
DarkChem	[M-H]-	124.412	31661259
DeepCCS	[M+H]+	127.084	30932474
DeepCCS	[M-H]-	123.866	30932474
DeepCCS	[M-2H]-	160.854	30932474
DeepCCS	[M+Na]+	136.244	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	128.1	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	126.4	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	132.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylerythritol	CC(O)(CO)[C@@H](O)CO	2543.9	Standard polar	33892256
2-Methylerythritol	CC(O)(CO)[C@@H](O)CO	1345.4	Standard non polar	33892256
2-Methylerythritol	CC(O)(CO)[C@@H](O)CO	1249.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methylerythritol,1TMS,isomer #1	CC(CO)(O[Si](C)(C)C)[C@@H](O)CO	1349.7	Semi standard non polar	33892256
2-Methylerythritol,1TMS,isomer #2	CC(O)(CO[Si](C)(C)C)[C@@H](O)CO	1359.9	Semi standard non polar	33892256
2-Methylerythritol,1TMS,isomer #3	CC(O)(CO)[C@H](CO)O[Si](C)(C)C	1327.4	Semi standard non polar	33892256
2-Methylerythritol,1TMS,isomer #4	CC(O)(CO)[C@@H](O)CO[Si](C)(C)C	1344.2	Semi standard non polar	33892256
2-Methylerythritol,2TMS,isomer #1	CC(CO[Si](C)(C)C)(O[Si](C)(C)C)[C@@H](O)CO	1424.8	Semi standard non polar	33892256
2-Methylerythritol,2TMS,isomer #2	CC(CO)(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	1407.7	Semi standard non polar	33892256
2-Methylerythritol,2TMS,isomer #3	CC(CO)(O[Si](C)(C)C)[C@@H](O)CO[Si](C)(C)C	1423.3	Semi standard non polar	33892256
2-Methylerythritol,2TMS,isomer #4	CC(O)(CO[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	1395.4	Semi standard non polar	33892256
2-Methylerythritol,2TMS,isomer #5	CC(O)(CO[Si](C)(C)C)[C@@H](O)CO[Si](C)(C)C	1415.2	Semi standard non polar	33892256
2-Methylerythritol,2TMS,isomer #6	CC(O)(CO)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	1395.2	Semi standard non polar	33892256
2-Methylerythritol,3TMS,isomer #1	CC(CO[Si](C)(C)C)(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	1466.6	Semi standard non polar	33892256
2-Methylerythritol,3TMS,isomer #2	CC(CO[Si](C)(C)C)(O[Si](C)(C)C)[C@@H](O)CO[Si](C)(C)C	1471.6	Semi standard non polar	33892256
2-Methylerythritol,3TMS,isomer #3	CC(CO)(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	1455.9	Semi standard non polar	33892256
2-Methylerythritol,3TMS,isomer #4	CC(O)(CO[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	1434.8	Semi standard non polar	33892256
2-Methylerythritol,4TMS,isomer #1	CC(CO[Si](C)(C)C)(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	1517.8	Semi standard non polar	33892256
2-Methylerythritol,1TBDMS,isomer #1	CC(CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	1598.9	Semi standard non polar	33892256
2-Methylerythritol,1TBDMS,isomer #2	CC(O)(CO[Si](C)(C)C(C)(C)C)[C@@H](O)CO	1587.7	Semi standard non polar	33892256
2-Methylerythritol,1TBDMS,isomer #3	CC(O)(CO)[C@H](CO)O[Si](C)(C)C(C)(C)C	1556.0	Semi standard non polar	33892256
2-Methylerythritol,1TBDMS,isomer #4	CC(O)(CO)[C@@H](O)CO[Si](C)(C)C(C)(C)C	1575.7	Semi standard non polar	33892256
2-Methylerythritol,2TBDMS,isomer #1	CC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	1858.3	Semi standard non polar	33892256
2-Methylerythritol,2TBDMS,isomer #2	CC(CO)(O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	1857.7	Semi standard non polar	33892256
2-Methylerythritol,2TBDMS,isomer #3	CC(CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO[Si](C)(C)C(C)(C)C	1854.8	Semi standard non polar	33892256
2-Methylerythritol,2TBDMS,isomer #4	CC(O)(CO[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	1838.8	Semi standard non polar	33892256
2-Methylerythritol,2TBDMS,isomer #5	CC(O)(CO[Si](C)(C)C(C)(C)C)[C@@H](O)CO[Si](C)(C)C(C)(C)C	1848.7	Semi standard non polar	33892256
2-Methylerythritol,2TBDMS,isomer #6	CC(O)(CO)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1845.7	Semi standard non polar	33892256
2-Methylerythritol,3TBDMS,isomer #1	CC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	2122.6	Semi standard non polar	33892256
2-Methylerythritol,3TBDMS,isomer #2	CC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO[Si](C)(C)C(C)(C)C	2129.1	Semi standard non polar	33892256
2-Methylerythritol,3TBDMS,isomer #3	CC(CO)(O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2133.9	Semi standard non polar	33892256
2-Methylerythritol,3TBDMS,isomer #4	CC(O)(CO[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2115.5	Semi standard non polar	33892256
2-Methylerythritol,4TBDMS,isomer #1	CC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2375.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylerythritol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-9000000000-7e4e7672c11a6f38d58e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylerythritol GC-MS (4 TMS) - 70eV, Positive	splash10-0abi-9256500000-4488acec35fa28a4729c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylerythritol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylerythritol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 10V, Positive-QTOF	splash10-00kr-1900000000-3d4da02cca74e8661ce3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 20V, Positive-QTOF	splash10-08fr-9100000000-aa5dbc8bde3ddd8a8ada	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 40V, Positive-QTOF	splash10-0a4i-9200000000-4ce1f0c31e904689acaa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 10V, Negative-QTOF	splash10-059i-6900000000-840be55e94295c91bf51	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 20V, Negative-QTOF	splash10-0abi-9300000000-4bca42c5d391d6238fd2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 40V, Negative-QTOF	splash10-0a4i-9000000000-5973a28a3a5b3302b8d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 10V, Negative-QTOF	splash10-052r-6900000000-072ae28521ba94e55e74	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 20V, Negative-QTOF	splash10-0a4i-9100000000-7e7e2fc485eb5b008fdd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 40V, Negative-QTOF	splash10-0a4l-9000000000-c4337458c61f4f7185b6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 10V, Positive-QTOF	splash10-0pvi-9600000000-2d6c724a76220fbb1f72	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 20V, Positive-QTOF	splash10-06r6-9100000000-71e5921f92379b4f07cf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylerythritol 40V, Positive-QTOF	splash10-0a4j-9000000000-693d14528e5ccdf90b0b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	25.3 (17.0-49.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21336380	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028350

KNApSAcK ID

C00052127

Chemspider ID

111356

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481015

PDB ID

Not Available

ChEBI ID

86367

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for 2-Methylerythritol (HMDB0011659)

MOL for HMDB0011659 (2-Methylerythritol)

3D MOL for HMDB0011659 (2-Methylerythritol)

3D SDF for HMDB0011659 (2-Methylerythritol)

3D-SDF for HMDB0011659 (2-Methylerythritol)

PDB for HMDB0011659 (2-Methylerythritol)

3D PDB for HMDB0011659 (2-Methylerythritol)

SMILES for HMDB0011659 (2-Methylerythritol)

INCHI for HMDB0011659 (2-Methylerythritol)

Structure for HMDB0011659 (2-Methylerythritol)

3D Structure for HMDB0011659 (2-Methylerythritol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra