Showing metabocard for Hydroxypropionic acid (MMDBc0000364)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:11 UTC
Update Date2022-08-31 06:02:40 UTC
Metabolite IDMMDBc0000364
Metabolite Identification
Common NameHydroxypropionic acid
Description3-Hydroxypropionic acid is a carboxylic acid. It is an intermediate in the breakdown of branched-chain amino acids and propionic acid from the gut. Typically it originates from propionyl-CoA and a defect in the enzyme propionyl carboxylase. This leads to a buildup in propionyl-CoA in the mitochondria.  Such a buildup can lead to a disruption of the esterified CoA:free CoA ratio and ultimately to mitochondrial toxicity. Detoxification of these metabolic end products occurs via the transfer of the propionyl moiety to carnitine-forming propionyl-carnitine, which is then transferred across the inner mitochondrial membrane. 3-Hydroxypropionic acid is then released as the free acid. As an industrial chemical, it is used in the production of various chemicals such as acrylates in industry. When present in sufficiently high levels, 3-hydroxypropionic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of hydroxypropionic acid are associated with many inborn errors of metabolism including biotinidase deficiency, malonic aciduria, methylmalonate semialdehyde dehydrogenase deficiency, methylmalonic aciduria, methylmalonic aciduria due to cobalamin-related disorders, and propionic acidemia. Hydroxypropionic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. Infants with acidosis have symptoms that include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. 3-Hydroxypropionic acid is also a microbial metabolite found in Escherichia, Klebsiella and Saccharomyces (PMID: 26360870 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x000055d249feaf30>


  Mrv1652305271900162D          

  6  5  0  0  0  0            999 V2000
10000.0136 9999.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2987 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5838 9999.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.298710000.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7283 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4461 9999.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x000055d249feaf30>

HMDB0000700
     RDKit          3D
Hydroxypropionic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.5702    0.0339   -1.6672 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008   -0.2378   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1391    0.0333    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -0.7902   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042    0.1471    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    1.3280   -0.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003    1.0494    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -1.7281    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -0.9701   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    0.3205    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9929   -0.3961    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.2101   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  4  8  1  0
  4  9  1  0
  5 10  1  0
  5 11  1  0
  6 12  1  0
M  END
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3D SDF for #<Metabolite:0x000055d249feaf30>


  Mrv1652305271900162D          

  6  5  0  0  0  0            999 V2000
10000.0136 9999.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2987 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5838 9999.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.298710000.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7283 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4461 9999.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000364

> <DATABASE_NAME>
MIME

> <SMILES>
OCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)

> <INCHI_KEY>
ALRHLSYJTWAHJZ-UHFFFAOYSA-N

> <FORMULA>
C3H6O3

> <MOLECULAR_WEIGHT>
90.0779

> <EXACT_MASS>
90.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.150999882309067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxypropanoic acid

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-0.8035810240000001

> <ALOGPS_LOGS>
0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.02280713040642

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.201252954149806

> <JCHEM_PKA_STRONGEST_BASIC>
-2.477742482637333

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
19.0453

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.47e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxypropionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x000055d249feaf30>

HMDB0000700
     RDKit          3D
Hydroxypropionic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.5702    0.0339   -1.6672 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008   -0.2378   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1391    0.0333    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -0.7902   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042    0.1471    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    1.3280   -0.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003    1.0494    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -1.7281    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -0.9701   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    0.3205    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9929   -0.3961    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.2101   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  4  8  1  0
  4  9  1  0
  5 10  1  0
  5 11  1  0
  6 12  1  0
M  END
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PDB for #<Metabolite:0x000055d249feaf30>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8666.6928665.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.3588666.290   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8664.0238665.521   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8665.3588667.831   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8668.0268666.290   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8669.3668665.521   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for #<Metabolite:0x000055d249feaf30>

COMPND    HMDB0000700
HETATM    1  O1  UNL     1       1.570   0.034  -1.667  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.201  -0.238  -0.496  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.139   0.033   0.522  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.111  -0.790  -0.180  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.004   0.147   0.588  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.276   1.328  -0.045  1.00  0.00           O  
HETATM    7  H1  UNL     1       2.200   1.049   0.746  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.011  -1.728   0.367  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.654  -0.970  -1.149  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.630   0.321   1.625  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.993  -0.396   0.694  1.00  0.00           H  
HETATM   12  H6  UNL     1      -1.430   1.210  -1.005  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    7
CONECT    4    5    8    9
CONECT    5    6   10   11
CONECT    6   12
END
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SMILES for #<Metabolite:0x000055d249feaf30>

OCCC(O)=O
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INCHI for #<Metabolite:0x000055d249feaf30>

InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
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Synonyms
ValueSource
3-HYDROXY-propanoIC ACIDChEBI
3-Hydroxypropanoic acidChEBI
beta-Hydroxypropionic acidChEBI
Hydracrylic acidChEBI
3-HydroxypropionateKegg
3-Hydroxypropionic acidKegg
3-HYDROXY-propanoateGenerator
3-HydroxypropanoateGenerator
b-HydroxypropionateGenerator
b-Hydroxypropionic acidGenerator
beta-HydroxypropionateGenerator
Β-hydroxypropionateGenerator
Β-hydroxypropionic acidGenerator
HydracrylateGenerator
HydroxypropionateGenerator
2-DeoxyglycerateHMDB
2-Deoxyglyceric acidHMDB
b-LactateHMDB
b-Lactic acidHMDB
beta-LactateHMDB
beta-Lactic acidHMDB
EthylenelactateHMDB
Ethylenelactic acidHMDB
Molecular FormulaC3H6O3
Average Mass90.0779
Monoisotopic Mass90.031694058
IUPAC Name3-hydroxypropanoic acid
Traditional Namehydroxypropionic acid
CAS Registry NumberNot Available
SMILES
OCCC(O)=O
InChI Identifier
InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
InChI KeyALRHLSYJTWAHJZ-UHFFFAOYSA-N