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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:50:07 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254499

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Metaldehyde

Description

Metaldehyde belongs to the class of organic compounds known as acetals. Acetals are compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups. Metaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Metaldehyde is a potentially toxic compound. Metaldehyde is also irritant to eyes and skin. It also competitively inhibits biogenic amine oxidation which, in turn, decreases 5-hydroxyindoleacetic acid (5-HIAA), a metabolite of 5-HT by competitively inhibiting 5-HT-oxidation. Acetaldehyde acts as a releasing factor for 5-hydroxytryptamine (5-HT) and noradrenaline (NA). Metaldehyde intoxicatin leads to central nervous system depression, and liver and kidney injury. There is no specific antidote. Death from respiratory failure can occur within a few hours of exposure. This compound has been identified in human blood as reported by (PMID: 31557052 ). Metaldehyde is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Metaldehyde is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.411   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.871   0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.282  -0.653   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.859  -1.242   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.859  -2.782   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.436  -0.653   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.153   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.693   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.436   2.193   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.859   2.782   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.859   4.322   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.282   2.193   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0254499
HETATM    1  C1  UNL     1      -0.206   2.764  -0.760  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.357   1.606   0.076  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.972   0.747  -0.767  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.731  -0.234  -0.211  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.855   0.225   0.656  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.881  -1.143   0.462  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.004  -1.551  -0.563  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.622  -2.841  -0.135  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.889  -0.525  -0.751  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.258  -0.011   0.467  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.779   0.169   0.433  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.641   1.129   0.851  1.00  0.00           O  
HETATM   13  H1  UNL     1      -0.195   3.711  -0.211  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.227   2.503  -1.114  1.00  0.00           H  
HETATM   15  H3  UNL     1       0.434   2.916  -1.665  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.130   2.085   0.733  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.179  -0.837  -1.043  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.338  -0.690   1.085  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.545   0.837   1.508  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.624   0.691   0.010  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.545  -1.724  -1.503  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.168  -2.781   0.822  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.226  -3.257  -0.966  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.213  -3.567   0.037  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.074  -0.791   1.261  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.134   0.884   1.173  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.251  -0.813   0.673  1.00  0.00           H  
HETATM   28  H16 UNL     1      -3.129   0.498  -0.558  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   12   16
CONECT    3    4
CONECT    4    5    6   17
CONECT    5   18   19   20
CONECT    6    7
CONECT    7    8    9   21
CONECT    8   22   23   24
CONECT    9   10
CONECT   10   11   12   25
CONECT   11   26   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Metacetaldehyde	MeSH

Chemical Formula

C₈H₁₆O₄

Average Molecular Weight

176.2102

Monoisotopic Molecular Weight

176.104859

IUPAC Name

2,4,6,8-tetramethyl-1,3,5,7-tetraoxocane

Traditional Name

metaldehyde

CAS Registry Number

Not Available

SMILES

CC1OC(C)OC(C)OC(C)O1

InChI Identifier

InChI=1S/C8H16O4/c1-5-9-6(2)11-8(4)12-7(3)10-5/h5-8H,1-4H3

InChI Key

GKKDCARASOJPNG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetals. Acetals are compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Acetals

Alternative Parents

Substituents

Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

acetal (CHEBI:81931 )
Molluscacide (C18744 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0254499)
extracellular (HMDB: HMDB0254499)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	0.96	ALOGPS
logP	1.17	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.78 m³·mol⁻¹	ChemAxon
Polarizability	18.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	149.629	30932474
DeepCCS	[M-H]-	146.323	30932474
DeepCCS	[M-2H]-	183.303	30932474
DeepCCS	[M+Na]+	158.897	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	135.8	32859911
AllCCS	[M+NH4]+	144.0	32859911
AllCCS	[M+Na]+	145.1	32859911
AllCCS	[M-H]-	138.9	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	142.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
METALDEHYDE	CC1OC(C)OC(C)OC(C)O1	1387.8	Standard polar	33892256
METALDEHYDE	CC1OC(C)OC(C)OC(C)O1	1009.8	Standard non polar	33892256
METALDEHYDE	CC1OC(C)OC(C)OC(C)O1	1038.2	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 - Metaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0043-9600000000-aff896a31bab36179c25	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-addd53e7c97dd0a41373	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 10V, Positive-QTOF	splash10-004i-1900000000-3a0583ef3e71ce6c831d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 20V, Positive-QTOF	splash10-000j-9200000000-bc04a03537d8c1fc6e1b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 40V, Positive-QTOF	splash10-004i-9000000000-fb4cb731680420af219e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 10V, Negative-QTOF	splash10-004i-0900000000-1fbd74de738f9bd884cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 20V, Negative-QTOF	splash10-004i-2900000000-1526b460542bcfef4922	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 40V, Negative-QTOF	splash10-0a4l-9100000000-9c9a1554992bbbe5388a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 10V, Positive-QTOF	splash10-004i-0900000000-ca808b2786d3287a7be2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 20V, Positive-QTOF	splash10-004i-2900000000-5a5f4674bce9964d8be1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 40V, Positive-QTOF	splash10-006t-9100000000-c5f5078331472e7678c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 10V, Negative-QTOF	splash10-05i9-9500000000-7198ed360e8398923d71	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 20V, Negative-QTOF	splash10-052f-9000000000-e7d24bbcda04dd8a7b2f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metaldehyde 40V, Negative-QTOF	splash10-052f-9100000000-7de1757678e99237833f	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18744

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metaldehyde

METLIN ID

Not Available

PubChem Compound

61021

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Metaldehyde (HMDB0254499)

MOL for HMDB0254499 (Metaldehyde)

3D MOL for HMDB0254499 (Metaldehyde)

3D SDF for HMDB0254499 (Metaldehyde)

3D-SDF for HMDB0254499 (Metaldehyde)

PDB for HMDB0254499 (Metaldehyde)

3D PDB for HMDB0254499 (Metaldehyde)

SMILES for HMDB0254499 (Metaldehyde)

INCHI for HMDB0254499 (Metaldehyde)

Structure for HMDB0254499 (Metaldehyde)

3D Structure for HMDB0254499 (Metaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra