Showing metabocard for Glyceraldehyde (BMDB0001051)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:24 UTC
Update Date2020-05-21 16:28:42 UTC
BMDB IDBMDB0001051
Secondary Accession Numbers
  • BMDB01051
Metabolite Identification
Common NameGlyceraldehyde
DescriptionGlyceraldehyde, also known as aldotriose or glycerose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Glyceraldehyde exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glyceraldehyde exists in all living species, ranging from bacteria to humans. Glyceraldehyde is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-GlyceraldehydeChEBI
2,3-DihydroxypropanalChEBI
2,3-DihydroxypropionaldehydeChEBI
AldotrioseChEBI
alpha,beta-DihydroxypropionaldehydeChEBI
DL-GlyceraldehydeChEBI
GliceraldehidoChEBI
GlyceraldehydChEBI
Glyceric aldehydeChEBI
GlycerinaldehydChEBI
GlycerinaldehydeChEBI
GlycerinformalChEBI
GlyceroseChEBI
GlyzerinaldehydChEBI
a,b-DihydroxypropionaldehydeGenerator
Α,β-dihydroxypropionaldehydeGenerator
(+/-)-2,3-dihydroxy-propanalHMDB
(+/-)-glyceraldehydeHMDB
D-(+)-GlyceraldehydeHMDB
D-2,3-DihydroxypropanalHMDB
D-2,3-DihydroxypropionaldehydeHMDB
D-AldotrioseHMDB
D-GlyceraldehydeHMDB
D-GlyceroseHMDB
delta-(+)-GlyceraldehydeHMDB
delta-2,3-DihydroxypropanalHMDB
delta-2,3-DihydroxypropionaldehydeHMDB
delta-AldotrioseHMDB
delta-GlyceraldehydeHMDB
delta-GlyceroseHMDB
DihydroxypropionaldehydeHMDB
Chemical FormulaC3H6O3
Average Molecular Weight90.0779
Monoisotopic Molecular Weight90.031694058
IUPAC Name2,3-dihydroxypropanal
Traditional Name(+/-)-glyceraldehyde
CAS Registry Number56-82-6
SMILES
OCC(O)C=O
InChI Identifier
InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2
InChI KeyMNQZXJOMYWMBOU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • 1,2-diol
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility17 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-1.7ChemAxon
logS0.96ALOGPS
pKa (Strongest Acidic)12.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.46 m³·mol⁻¹ChemAxon
Polarizability8.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0250760
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022392
KNApSAcK IDC00007413
Chemspider ID731
KEGG Compound IDC02154
BioCyc IDCPD0-1551
BiGG IDNot Available
Wikipedia LinkGlyceraldehyde
METLIN IDNot Available
PubChem Compound751
PDB IDNot Available
ChEBI ID5445
References
Synthesis ReferenceWan, Xin-Jun; Song, Ming-You; Wu, Rong; Chu, Dao-Bao. Synthesis of glyceraldehyde by indirect electrooxidation. Yingyong Huaxue (2003), 20(6), 578-581.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]

Enzymes

Enzyme Details
1. Fructose-bisphosphate aldolase B
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
Q3T0S5
Molecular weight:
39543.0
Reactions
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
Enzyme Details
2. Aldo-keto reductase family 1 member B1
General function:
Involved in 20-alpha-hydroxysteroid dehydrogenase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols. Displays enzymatic activity towards endogenous metabolites such as aromatic and aliphatic aldehydes, ketones, monosacharides, bile acids and xenobiotics substrates. Key enzyme in the polyol pathway, catalyzes reduction of glucose to sorbitol during hyperglycemia. Reduces steroids and their derivatives and prostaglandins. Displays low enzymatic activity toward all-trans-retinal, 9-cis-retinal, and 13-cis-retinal. Catalyzes the reduction of diverse phospholipid aldehydes such as 1-palmitoyl-2-(5-oxovaleroyl)-sn -glycero-3-phosphoethanolamin (POVPC) and related phospholipid aldehydes that are generated from the oxydation of phosphotidylcholine and phosphatdyleethanolamides. Plays a role in detoxifying dietary and lipid-derived unsaturated carbonyls, such as crotonaldehyde, 4-hydroxynonenal, trans-2-hexenal, trans-2,4-hexadienal and their glutathione-conjugates carbonyls (GS-carbonyls).
Gene Name:
AKR1B1
Uniprot ID:
P16116
Molecular weight:
35919.0
Reactions
Glyceraldehyde + NADP → Glycerol + NADPHdetails
Enzyme Details
3. Aldehyde dehydrogenase family 3 member B1
General function:
Energy production and conversion
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. Can use both NADP(+) and NAD(+) as electron acceptor. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
Q1JPA0
Molecular weight:
51800.0
Reactions
Glyceric acid + NADP + Water → Glyceraldehyde + NADPHdetails