Bovine Metabolome Database: Showing metabocard for Succinic acid semialdehyde (BMDB0001259)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:43:11 UTC

Update Date

2020-05-19 22:00:56 UTC

BMDB ID

BMDB0001259

Secondary Accession Numbers

BMDB01259

Metabolite Identification

Common Name

Succinic acid semialdehyde

Description

Succinic acid semialdehyde, also known as Succinic acid semialdehyde or Succinic acid semialdehyde, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Succinic acid semialdehyde is a drug. Succinic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Succinic acid semialdehyde exists in all living species, ranging from bacteria to humans. Succinic acid semialdehyde participates in a number of enzymatic reactions, within cattle. In particular, Succinic acid semialdehyde and L-glutamic acid can be biosynthesized from gamma-aminobutyric acid and oxoglutaric acid through its interaction with the enzyme 4-aminobutyrate aminotransferase, mitochondrial. In addition, Succinic acid semialdehyde can be converted into succinic acid; which is mediated by the enzyme succinate-semialdehyde dehydrogenase, mitochondrial. In cattle, succinic acid semialdehyde is involved in the metabolic pathway called the glutamate metabolism pathway. Succinic acid semialdehyde is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Formylpropanoic acid	ChEBI
3-Formylpropionic acid	ChEBI
4-Oxobutanoate	ChEBI
beta-Formylpropionic acid	ChEBI
Semialdehyde succinique	ChEBI
Succinaldehydic acid	ChEBI
Succinate semialdehyde	ChEBI
Succinic semialdehyde	Kegg
3-Formylpropanoate	Generator
3-Formylpropionate	Generator
4-Oxobutanoic acid	Generator
b-Formylpropionate	Generator
b-Formylpropionic acid	Generator
beta-Formylpropionate	Generator
Β-formylpropionate	Generator
Β-formylpropionic acid	Generator
Succinaldehydate	Generator
2-Formylpropionic acid ethyl ester	HMDB
Butryaldehydate	HMDB
Butryaldehydic acid	HMDB
gamma-Oxybutyrate	HMDB
gamma-Oxybutyric acid	HMDB
Succinic semialdehyde, calcium salt	HMDB
Succinic acid semialdehyde	ChEBI

Chemical Formula

C₄H₆O₃

Average Molecular Weight

102.0886

Monoisotopic Molecular Weight

102.031694058

IUPAC Name

4-oxobutanoic acid

Traditional Name

succinic semialdehyde

CAS Registry Number

692-29-5

SMILES

OC(=O)CCC=O

InChI Identifier

InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)

InChI Key

UIUJIQZEACWQSV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

Straight chain fatty acid
Alpha-hydrogen aldehyde
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aldehydic acid (CHEBI:16265 )
Fatty aldehydes (LMFA06000118 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane
Mitochondria

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.47	ALOGPS
logP	-0.56	ChemAxon
logS	0.28	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	22.61 m³·mol⁻¹	ChemAxon
Polarizability	9.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9400000000-8e1cb554add6ed6c4e35	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9300000000-f5403e2e858fded273ac	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9400000000-8e1cb554add6ed6c4e35	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9300000000-f5403e2e858fded273ac	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9500000000-eb52f4d003b7d5b86b3d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9600000000-463f366ebd0be24a0283	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-d9618eb947af434dcf2f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9800000000-40373963cdda851ebfea	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-bf9ebea7e4800559c111	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-0900000000-64b3498f7cdd4597da6a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-1900000000-9d47aab2400f1da945bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-1900000000-94e1ac309574efbe3903	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-3900000000-7ec96b67f820176c39d3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0udi-5900000000-7708b3a1c05b69363aa9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0zfr-8900000000-12726b727f621ac971b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0089-9000000000-9eb7dd16da8275702c75	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-1900000000-567d38fac821ab993d19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-e31b8066f970e1c178d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052u-9000000000-76526f6c67d7a67c1d07	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-70e85383e59b46bc429f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-f1c2507387f92b6e1e3f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgi-9400000000-ba1b880a90d3ace8beee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-971836bb1672ad33106e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-9000000000-06109e02fc0baa708cdc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-ce51d68c1c700db8f966	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d171f37acc222eeea075	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9100000000-b23feac6075bc2594f5e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-aa34fb8bd9988d794431	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-101491882eb1be877e89	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane
Mitochondria

Biospecimen Locations

Blood
Liver
Mammary Gland
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glutamate Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25599412	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001259

DrugBank ID

DBMET01476

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Succinic semialdehyde

METLIN ID

6114

PubChem Compound

1112

PDB ID

Not Available

ChEBI ID

16265

References

Synthesis Reference

Bruce, R.; Sims, K.; Pitts, F. N., Jr. Synthesis and purification of succinic semialdehyde. Analytical Biochemistry (1971), 41(1), 271-3.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Hydroxyacid-oxoacid transhydrogenase, mitochondrial

General function:: Energy production and conversion
Specific function:: Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). L-3-hydroxybutyrate (L-3-OHB) is also a substrate for HOT when using 2-KG as hydrogen acceptor, resulting in the formation of D-2-HG (By similarity).
Gene Name:: ADHFE1
Uniprot ID:: A6QP15
Molecular weight:: 50343.0

Enzyme Details

2. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine (By similarity).
Gene Name:: ABAT
Uniprot ID:: Q9BGI0
Molecular weight:: 56731.0

Reactions

Gamma-Aminobutyric acid + Oxoglutaric acid → Succinic acid semialdehyde + L-Glutamic acid	details

Showing metabocard for Succinic acid semialdehyde (BMDB0001259)

Structure for BMDB0001259 (Succinic acid semialdehyde)

Enzymes

Reactions