MiMeDB: Showing metabocard for 3-Methyl-2-butenal (MMDBc0051700)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 20:31:42 UTC

Update Date

2024-04-30 20:43:01 UTC

Metabolite ID

MMDBc0051700

Metabolite Identification

Common Name

3-Methyl-2-butenal

Description

3-Methyl-2-butenal, also known as senecialdehyde or 3,3-dimethylacrolein, belongs to the class of organic compounds known as enals. These are alpha,beta-unsaturated aldehydes of the general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. 3-methyl-2-butenal has been detected, but not quantified, in several different foods, such as common oregano, beechnuts, oval-leaf huckleberries, tea leaf willows, and red rice. This could make 3-methyl-2-butenal a potential biomarker for the consumption of these foods. 3-Methyl-2-butenal is a derivative of acrolein that is an alpha, beta-unsaturated carbonyl metabolite. It can be formed endogenously during lipid peroxidation or after oxidative stress, and is considered to play an important role in human carcinogenesis. The endogenously formed acroleins are a constant source of DNA damage, can lead to mutation, and can also induce tumours in humans (PMID:8319634 ). 3-Methyl-2-butenal, which is an unsaturated aldehyde bearing substitution at the alkene terminus, is a poor inactivator of the enzymes protein tyrosine phosphatases (PTPs). The inactivation of PTPs can yield profound biological consequences arising from the disruption of cellular signalling pathways (PMID:17655273 ).

Structure

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

Synonyms

Value	Source
3,3-Dimethyl-acrylaldehyde	ChEBI
3,3-Dimethylacrolein	ChEBI
3-Methylcrotonaldehyde	ChEBI
beta,beta-Dimethylacrolein	ChEBI
beta-Methylcrotonaldehyde	ChEBI
Prenal	ChEBI
Senecialdehyde	ChEBI
Senecioaldehyde	ChEBI
b,b-Dimethylacrolein	Generator
Β,β-dimethylacrolein	Generator
b-Methylcrotonaldehyde	Generator
Β-methylcrotonaldehyde	Generator
3-Methylbut-2-enal	HMDB
beta,beta-Dimethylacrylic aldehyde	HMDB
2-Methyl-2-buten-4-al	HMDB
3,3-Dimethylacrylaldehyde	HMDB
3-Methyl-2-buten-1-al	HMDB
3-Methyl-2-butenal	HMDB
3-Methyl-2-butenaldehyde	HMDB
β,β-Dimethylacrylic aldehyde	HMDB

Molecular Formula

C₅H₈O

Average Mass

84.1164

Monoisotopic Mass

84.057514878

IUPAC Name

3-methylbut-2-enal

Traditional Name

prenal

CAS Registry Number

Not Available

SMILES

CC(C)=CC=O

InChI Identifier

InChI=1S/C5H8O/c1-5(2)3-4-6/h3-4H,1-2H3

InChI Key

SEPQTYODOKLVSB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enals

Alternative Parents

Substituents

Enal
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:15825 )
a small molecule (PRENAL )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	63.6 g/L	ALOGPS
logP	0.97	ALOGPS
logP	1	ChemAxon
logS	-0.12	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.32 m³·mol⁻¹	ChemAxon
Polarizability	9.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a5c-9000000000-1ec92de58f3b78822176	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a5c-9000000000-1ec92de58f3b78822176	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9000000000-5092b9dfda47020345ed	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-de8a6eec89362bfff45a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-0865f5d08c1ce95bdd58	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9000000000-32ba84192db5d33a736c	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-392e24493caefed8d41d	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-2568b7ba82ce5430fe4b	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-1cc850ae9a5dbeac5dc7	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-bb5ff4f4247f9b92d7b4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-c6adf8b427f15f31188a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-44aeba383c0994cb6326	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-1fe8bbf8f6ab17ae0b2b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-6b3dd865845396e5b217	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-9b4ce98aee0a57ea1914	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-003r-9000000000-259c3199037e112aa7ef	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.54 MHz, CDCl₃, experimental)		2015-03-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191748	Carbonyl reductase [NADPH] 1	Enzyme	P16152	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2
Bacteria	Proteobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23454028

External Links

HMDB ID

HMDB0012157

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61020

PDB ID

Not Available

ChEBI ID

15825

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Eder E, Hoffman C, Sporer S, Scheckenbach S: Biomonitoring studies and susceptibility markers for acrolein congeners and allylic and benzyl compounds. Environ Health Perspect. 1993 Mar;99:245-7. doi: 10.1289/ehp.9399245. [PubMed:8319634 ]
Seiner DR, LaButti JN, Gates KS: Kinetics and mechanism of protein tyrosine phosphatase 1B inactivation by acrolein. Chem Res Toxicol. 2007 Sep;20(9):1315-20. doi: 10.1021/tx700213s. Epub 2007 Jul 27. [PubMed:17655273 ]

Showing metabocard for 3-Methyl-2-butenal (MMDBc0051700)

MOL for #<Metabolite:0x00007fecf0a05f48>

3D MOL for #<Metabolite:0x00007fecf0a05f48>

3D SDF for #<Metabolite:0x00007fecf0a05f48>

3D-SDF for #<Metabolite:0x00007fecf0a05f48>

PDB for #<Metabolite:0x00007fecf0a05f48>

3D PDB for #<Metabolite:0x00007fecf0a05f48>

SMILES for #<Metabolite:0x00007fecf0a05f48>

INCHI for #<Metabolite:0x00007fecf0a05f48>

Structure for #<Metabolite:0x00007fecf0a05f48>

3D Structure for #<Metabolite:0x00007fecf0a05f48>