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Showing metabocard for 3-Hydroxypropanal (HMDB0003453)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 21:20:02 UTC
Update Date2023-02-21 17:16:41 UTC
HMDB IDHMDB0003453
Secondary Accession Numbers
  • HMDB03453
Metabolite Identification
Common Name3-Hydroxypropanal
Description3-Hydroxypropanal is a broad-spectrum antimicrobial substance termed reuterin produced by Lactobacillus reuteri. L. reuteri resides in the gastrointestinal tract of healthy humans and animals, and is believed to. function as a symbiont in the enteric ecosystem. Synthesis of such an antimicrobial substance by an enteric resident raises a number of interesting questions and possibilities as to the role these residents may play in the health of the host. (PMID 3245697 ). In vivo, glycerol is converted in one enzymatic step into 3-Hydroxypropanal. The 3-Hydroxypropanal -producing Lactobacillus reuteri is used as a probiotic in the health care of humans and animals. 3-Hydroxypropanal forms, together with Hydroxypropanal-hydrate and Hydroxypropanal-dimer, a dynamic, multi-component system (Hydroxypropanal system) used in food preservation, as a precursor for many modern chemicals such as acrolein, acrylic acid, and 1,3-propanediol (1,3-PDO), and for polymer production. 3-Hydroxypropanal can be obtained both through traditional chemistry and bacterial fermentation. To date, 3-HPA has been produced from petrochemical resources as an intermediate in 1,3-PDO production. The biotechnological production of 3-Hydroxypropanal from renewable resources is desirable both for use of 3-Hydroxypropanal in foods and for the production of bulk chemicals. The main challenge will be the efficient production and recovery of pure 3-Hydroxypropanal. (PMID 14669058 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003453 (3-Hydroxypropanal)

  Mrv0541 02231219442D          

  5  4  0  0  0  0            999 V2000
   12.0895  -15.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068  -15.7491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0895  -16.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3714  -16.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6537  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0003453 (3-Hydroxypropanal)

HMDB0003453
     RDKit          3D
3-Hydroxypropanal
 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.7864    1.7368   -0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345    0.6487    0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -0.5987    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175   -0.2471   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212    0.6218    0.3334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449    0.6480    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -1.3747   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -1.0241    1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6957    0.3193   -1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5150   -1.1553   -0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3234    0.4252    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
M  END
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3D SDF for HMDB0003453 (3-Hydroxypropanal)

  Mrv0541 02231219442D          

  5  4  0  0  0  0            999 V2000
   12.0895  -15.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068  -15.7491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0895  -16.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3714  -16.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6537  -16.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003453

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2

> <INCHI_KEY>
AKXKFZDCRYJKTF-UHFFFAOYSA-N

> <FORMULA>
C3H6O2

> <MOLECULAR_WEIGHT>
74.0785

> <EXACT_MASS>
74.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.262928954718575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxypropanal

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-0.9621972763333333

> <ALOGPS_LOGS>
0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.597544354273339

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.420195732575397

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4363702124560094

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
18.119899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-hydroxypropionaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0003453 (3-Hydroxypropanal)

HMDB0003453
     RDKit          3D
3-Hydroxypropanal
 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.7864    1.7368   -0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345    0.6487    0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -0.5987    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175   -0.2471   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212    0.6218    0.3334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449    0.6480    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -1.3747   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -1.0241    1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6957    0.3193   -1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5150   -1.1553   -0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3234    0.4252    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
M  END
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PDB for HMDB0003453 (3-Hydroxypropanal)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      22.567 -29.392   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.799 -29.398   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      22.567 -30.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.227 -31.691   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.887 -30.937   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    5                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    2    4                                                       
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0003453 (3-Hydroxypropanal)

COMPND    HMDB0003453
HETATM    1  O1  UNL     1      -0.786   1.737  -0.144  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.234   0.649   0.178  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.448  -0.599   0.038  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.917  -0.247  -0.544  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.521   0.622   0.333  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.245   0.648   0.573  1.00  0.00           H  
HETATM    7  H2  UNL     1      -0.941  -1.375  -0.560  1.00  0.00           H  
HETATM    8  H3  UNL     1      -0.318  -1.024   1.068  1.00  0.00           H  
HETATM    9  H4  UNL     1       0.696   0.319  -1.486  1.00  0.00           H  
HETATM   10  H5  UNL     1       1.515  -1.155  -0.750  1.00  0.00           H  
HETATM   11  H6  UNL     1       1.323   0.425   1.295  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4    7    8
CONECT    4    5    9   10
CONECT    5   11
END
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SMILES for HMDB0003453 (3-Hydroxypropanal)

OCCC=O
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INCHI for HMDB0003453 (3-Hydroxypropanal)

InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-HydroxypropionaldehydeHMDB, MeSH
3-oxo-1-PropanolHMDB
b-HydroxypropanalHMDB
b-HydroxypropionaldehydeHMDB
beta-HydroxypropanalHMDB
beta-HydroxypropionaldehydeHMDB, MeSH
HydracroleinHMDB
ReuterinHMDB, MeSH
3-HPAMeSH, HMDB
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Name3-hydroxypropanal
Traditional Nameβ-hydroxypropionaldehyde
CAS Registry Number2134-29-4
SMILES
OCCC=O
InChI Identifier
InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2
InChI KeyAKXKFZDCRYJKTF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023176
KNApSAcK IDNot Available
Chemspider ID67601
KEGG Compound IDC00969
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkReuterin
METLIN ID6935
PubChem Compound75049
PDB IDNot Available
ChEBI ID17871
Food Biomarker OntologyNot Available
VMH ID3HPPNL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLu, Shunfeng; Wang, Shiliang; Peng, Bin; Qin, Yanhuang; Zhou, Zhiquan; Wu, Xiuxiang. Process for preparation of 3-hydroxypropanal and 1,3-propanediol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 10 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Olivares M, Diaz-Ropero MP, Martin R, Rodriguez JM, Xaus J: Antimicrobial potential of four Lactobacillus strains isolated from breast milk. J Appl Microbiol. 2006 Jul;101(1):72-9. [PubMed:16834593 ]
  2. Talarico TL, Casas IA, Chung TC, Dobrogosz WJ: Production and isolation of reuterin, a growth inhibitor produced by Lactobacillus reuteri. Antimicrob Agents Chemother. 1988 Dec;32(12):1854-8. [PubMed:3245697 ]
  3. Vollenweider S, Lacroix C: 3-hydroxypropionaldehyde: applications and perspectives of biotechnological production. Appl Microbiol Biotechnol. 2004 Mar;64(1):16-27. Epub 2003 Dec 11. [PubMed:14669058 ]