Showing Compound Card for Succinic acid semialdehyde (CDB005111)

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Record Information
Version1.0
Created at2020-04-17 19:10:24 UTC
Updated at2020-12-07 19:11:36 UTC
CannabisDB IDCDB005111
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSuccinic acid semialdehyde
DescriptionSuccinic 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Formylpropanoic acidChEBI
3-Formylpropionic acidChEBI
4-OxobutanoateChEBI
beta-Formylpropionic acidChEBI
Semialdehyde succiniqueChEBI
Succinaldehydic acidChEBI
Succinate semialdehydeChEBI
Succinic semialdehydeKegg
3-FormylpropanoateGenerator
3-FormylpropionateGenerator
4-Oxobutanoic acidGenerator
b-FormylpropionateGenerator
b-Formylpropionic acidGenerator
beta-FormylpropionateGenerator
Β-formylpropionateGenerator
Β-formylpropionic acidGenerator
SuccinaldehydateGenerator
2-Formylpropionic acid ethyl esterHMDB
ButryaldehydateHMDB
Butryaldehydic acidHMDB
gamma-OxybutyrateHMDB
gamma-Oxybutyric acidHMDB
Succinic semialdehyde, calcium saltHMDB
Succinic acid semialdehydeChEBI
Chemical FormulaC4H6O3
Average Molecular Weight102.09
Monoisotopic Molecular Weight102.0317
IUPAC Name4-oxobutanoic acid
Traditional Namesuccinic semialdehyde
CAS Registry Number692-29-5
SMILES
OC(=O)CCC=O
InChI Identifier
InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)
InChI KeyUIUJIQZEACWQSV-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.47ALOGPS
logP-0.56ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity22.61 m³·mol⁻¹ChemAxon
Polarizability9.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSSuccinic acid semialdehyde, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9400000000-8e1cb554add6ed6c4e35Spectrum
GC-MSSuccinic acid semialdehyde, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9300000000-f5403e2e858fded273acSpectrum
GC-MSSuccinic acid semialdehyde, non-derivatized, GC-MS Spectrumsplash10-000i-9400000000-8e1cb554add6ed6c4e35Spectrum
GC-MSSuccinic acid semialdehyde, non-derivatized, GC-MS Spectrumsplash10-000i-9300000000-f5403e2e858fded273acSpectrum
GC-MSSuccinic acid semialdehyde, non-derivatized, GC-MS Spectrumsplash10-000i-9500000000-eb52f4d003b7d5b86b3dSpectrum
GC-MSSuccinic acid semialdehyde, non-derivatized, GC-MS Spectrumsplash10-000i-9600000000-463f366ebd0be24a0283Spectrum
Predicted GC-MSSuccinic acid semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9000000000-d9618eb947af434dcf2fSpectrum
Predicted GC-MSSuccinic acid semialdehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9800000000-40373963cdda851ebfeaSpectrum
Predicted GC-MSSuccinic acid semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-bf9ebea7e4800559c1112012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-0900000000-64b3498f7cdd4597da6a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0udi-1900000000-9d47aab2400f1da945bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-1900000000-94e1ac309574efbe39032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0udi-3900000000-7ec96b67f820176c39d32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0udi-5900000000-7708b3a1c05b69363aa92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0zfr-8900000000-12726b727f621ac971b72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0089-9000000000-9eb7dd16da8275702c752020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-1900000000-567d38fac821ab993d192021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e31b8066f970e1c178d12015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-9000000000-76526f6c67d7a67c1d072015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-70e85383e59b46bc429f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f1c2507387f92b6e1e3f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgi-9400000000-ba1b880a90d3ace8beee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-971836bb1672ad33106e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-9000000000-06109e02fc0baa708cdc2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-ce51d68c1c700db8f9662021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-d171f37acc222eeea0752021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9100000000-b23feac6075bc2594f5e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-aa34fb8bd9988d7944312021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-101491882eb1be877e892021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
4-aminobutyrate aminotransferase, mitochondrialABAT16p13.2P80404 details
Succinate-semialdehyde dehydrogenase, mitochondrialALDH5A16p22P51649 details
Aflatoxin B1 aldehyde reductase member 2AKR7A21p36.13O43488 details
Hydroxyacid-oxoacid transhydrogenase, mitochondrialADHFE18q13.1Q8IWW8 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Hydroxyacid-oxoacid transhydrogenase, mitochondrialADHFE18q13.1Q8IWW8 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001259
DrugBank IDDBMET01476
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022516
KNApSAcK IDC00019682
Chemspider ID1080
KEGG Compound IDC00232
BioCyc IDSUCC-S-ALD
BiGG ID34331
Wikipedia LinkSuccinic semialdehyde
METLIN ID6114
PubChem Compound1112
PDB IDNot Available
ChEBI ID16265
References
General ReferencesNot 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