Cannabis Compound Database: Showing Compound Card for Succinic acid semialdehyde (CDB005111)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4) Show 5 proteins XML

Show more...Show more...Show more...Show more...

Record Information

Version

1.0

Created at

2020-04-17 19:10:24 UTC

Updated at

2020-12-07 19:11:36 UTC

CannabisDB ID

CDB005111

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Succinic acid semialdehyde

Description

Succinic acid semialdehyde, also known as 3-formylpropionic acid or 4-oxobutanoate, 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 very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Succinic acid semialdehyde is a potentially toxic compound. Succinic acid semialdehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

102.09

Monoisotopic Molecular Weight

102.0317

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Testicle

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Indirect biological role:

Industrial application:

Biological role:

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Succinic acid semialdehyde, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-9400000000-8e1cb554add6ed6c4e35	Spectrum
GC-MS	Succinic acid semialdehyde, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-9300000000-f5403e2e858fded273ac	Spectrum
GC-MS	Succinic acid semialdehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9400000000-8e1cb554add6ed6c4e35	Spectrum
GC-MS	Succinic acid semialdehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9300000000-f5403e2e858fded273ac	Spectrum
GC-MS	Succinic acid semialdehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9500000000-eb52f4d003b7d5b86b3d	Spectrum
GC-MS	Succinic acid semialdehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9600000000-463f366ebd0be24a0283	Spectrum
Predicted GC-MS	Succinic acid semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-9000000000-d9618eb947af434dcf2f	Spectrum
Predicted GC-MS	Succinic acid semialdehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-9800000000-40373963cdda851ebfea	Spectrum
Predicted GC-MS	Succinic acid semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-bf9ebea7e4800559c111	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-0900000000-64b3498f7cdd4597da6a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-1900000000-9d47aab2400f1da945bc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-1900000000-94e1ac309574efbe3903	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-3900000000-7ec96b67f820176c39d3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0udi-5900000000-7708b3a1c05b69363aa9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0zfr-8900000000-12726b727f621ac971b7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0089-9000000000-9eb7dd16da8275702c75	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-1900000000-567d38fac821ab993d19	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-e31b8066f970e1c178d1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052u-9000000000-76526f6c67d7a67c1d07	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-70e85383e59b46bc429f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-f1c2507387f92b6e1e3f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgi-9400000000-ba1b880a90d3ace8beee	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-971836bb1672ad33106e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-9000000000-06109e02fc0baa708cdc	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-ce51d68c1c700db8f966	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d171f37acc222eeea075	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9100000000-b23feac6075bc2594f5e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-aa34fb8bd9988d794431	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-101491882eb1be877e89	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glutamate Metabolism
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency		Not Available
Homocarnosinosis		Not Available
Hyperinsulinism-Hyperammonemia Syndrome		Not Available
2-Hydroxyglutric Aciduria (D And L Form)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
4-aminobutyrate aminotransferase, mitochondrial	ABAT	16p13.2	P80404	details
Succinate-semialdehyde dehydrogenase, mitochondrial	ALDH5A1	6p22	P51649	details
Aflatoxin B1 aldehyde reductase member 2	AKR7A2	1p36.13	O43488	details
Hydroxyacid-oxoacid transhydrogenase, mitochondrial	ADHFE1	8q13.1	Q8IWW8	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Hydroxyacid-oxoacid transhydrogenase, mitochondrial	ADHFE1	8q13.1	Q8IWW8	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001259

DrugBank ID

DBMET01476

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Enzymes

Enzyme Details

1. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Involved in 4-aminobutyrate transaminase activity
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.
Gene Name:: ABAT
Uniprot ID:: P80404
Molecular weight:: 56438.405

Enzyme Details

2. Succinate-semialdehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes one step in the degradation of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA).
Gene Name:: ALDH5A1
Uniprot ID:: P51649
Molecular weight:: 57214.23

Enzyme Details

3. Aflatoxin B1 aldehyde reductase member 2

General function:: Energy production and conversion
Specific function:: Catalyzes the NADPH-dependent reduction of succinic semialdehyde to gamma-hydroxybutyrate. May have an important role in producing the neuromodulator gamma-hydroxybutyrate (GHB). Has broad substrate specificity. Has NADPH-dependent aldehyde reductase activity towards 2-carboxybenzaldehyde, 2-nitrobenzaldehyde and pyridine-2-aldehyde (in vitro). Can reduce 1,2-naphthoquinone and 9,10-phenanthrenequinone (in vitro). Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen.
Gene Name:: AKR7A2
Uniprot ID:: O43488
Molecular weight:: 39588.65

Enzyme Details

4. Hydroxyacid-oxoacid transhydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
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). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
Gene Name:: ADHFE1
Uniprot ID:: Q8IWW8
Molecular weight:: 50307.42

Showing Compound Card for Succinic acid semialdehyde (CDB005111)

Structure for CDB005111 (Succinic acid semialdehyde)

Enzymes