Hmdb loader

Showing metabocard for 4-Hydroxycrotonic acid (HMDB0003381)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 19:55:15 UTC
Update Date2023-02-21 17:16:39 UTC
HMDB IDHMDB0003381
Secondary Accession Numbers
  • HMDB03381
Metabolite Identification
Common Name4-Hydroxycrotonic acid
Description4-Hydroxycrotonic acid was first identified in biopsies of renal tissue from patients with chronic glomerulonephritis. 4-Hydroxycrotonic acid is usually undetectable in normal urine and serum. Experimentally, 4-Hydroxycrotonic acid increases initially with kidney ischemia but later reaches almost control levels. (PMID: 7107749 , 6833421 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003381 (4-Hydroxycrotonic acid)

  Mrv0541 02231219422D          

  7  6  0  0  0  0            999 V2000
   23.8347  -11.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2622  -11.4989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9767  -10.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1201  -11.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4057  -11.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6912  -11.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9767  -11.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0003381 (4-Hydroxycrotonic acid)

HMDB0003381
     RDKit          3D
4-Hydroxycrotonic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.8180   -1.1540   -1.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619   -0.2122   -0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    0.4957   -0.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    0.0919    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -0.5624    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6511   -0.2362    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6702    0.0914    0.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    1.2917   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7489    0.9276    0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5224   -1.3762   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6308    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9761   -1.0738    1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7219    1.0855   -0.0238 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  2  0
  5  6  1  0
  6  7  1  0
  3  8  1  0
  4  9  1  0
  5 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
M  END
Download

3D SDF for HMDB0003381 (4-Hydroxycrotonic acid)

  Mrv0541 02231219422D          

  7  6  0  0  0  0            999 V2000
   23.8347  -11.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2622  -11.4989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9767  -10.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1201  -11.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4057  -11.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6912  -11.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9767  -11.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003381

> <DATABASE_NAME>
hmdb

> <SMILES>
OC\C=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h1-2,5H,3H2,(H,6,7)/b2-1+

> <INCHI_KEY>
RMQJECWPWQIIPW-OWOJBTEDSA-N

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
9.340497730779669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-hydroxybut-2-enoic acid

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
-0.3611888693333335

> <ALOGPS_LOGS>
0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.643719973318369

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.445132728497078

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5471423248043683

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
24.739599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxycrotonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003381 (4-Hydroxycrotonic acid)

HMDB0003381
     RDKit          3D
4-Hydroxycrotonic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.8180   -1.1540   -1.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619   -0.2122   -0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    0.4957   -0.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    0.0919    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -0.5624    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6511   -0.2362    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6702    0.0914    0.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    1.2917   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7489    0.9276    0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5224   -1.3762   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6308    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9761   -1.0738    1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7219    1.0855   -0.0238 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  2  0
  5  6  1  0
  6  7  1  0
  3  8  1  0
  4  9  1  0
  5 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
M  END
Download

PDB for HMDB0003381 (4-Hydroxycrotonic acid)

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      44.491 -20.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.823 -21.465   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      39.157 -19.155   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      43.158 -21.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      41.824 -20.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      40.490 -21.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.157 -20.695   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    7                                                            
CONECT    3    7                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    3    6                                                  
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for HMDB0003381 (4-Hydroxycrotonic acid)

COMPND    HMDB0003381
HETATM    1  O1  UNL     1       1.818  -1.154  -1.334  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.862  -0.212  -0.513  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.040   0.496  -0.387  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.681   0.092   0.264  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.451  -0.562   0.166  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.651  -0.236   0.971  1.00  0.00           C  
HETATM    7  O3  UNL     1      -2.670   0.091   0.101  1.00  0.00           O  
HETATM    8  H1  UNL     1       3.297   1.292  -0.950  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.749   0.928   0.981  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.522  -1.376  -0.530  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.453   0.631   1.631  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.976  -1.074   1.617  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.722   1.086  -0.024  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    8
CONECT    4    5    5    9
CONECT    5    6   10
CONECT    6    7   11   12
CONECT    7   13
END
Download

SMILES for HMDB0003381 (4-Hydroxycrotonic acid)

OC\C=C\C(O)=O
Download

INCHI for HMDB0003381 (4-Hydroxycrotonic acid)

InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h1-2,5H,3H2,(H,6,7)/b2-1+
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-HydroxycrotonateGenerator
trans-4-Hydroxycrotonic acidChEMBL, HMDB, MeSH
trans-4-HydroxycrotonateGenerator, HMDB
4-Hydroxy-2-butenoateHMDB
4-Hydroxy-2-butenoic acidHMDB
4-Hydroxy-crotonic acidHMDB
gamma-Hydroxy-crotonic acidHMDB
gamma-Hydroxycrotonic acidHMDB
4-Hydroxy-2-butenoic acid, (e)-isomerMeSH, HMDB
4-Hydroxy-2-butenoic acid, (Z)-isomerMeSH, HMDB
4-Hydroxy-2-butenoic acid, sodium salt, (e)-isomerMeSH, HMDB
4-Hydroxy-crotonateGenerator, HMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name(2E)-4-hydroxybut-2-enoic acid
Traditional Name4-hydroxycrotonic acid
CAS Registry Number24587-49-3
SMILES
OC\C=C\C(O)=O
InChI Identifier
InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h1-2,5H,3H2,(H,6,7)/b2-1+
InChI KeyRMQJECWPWQIIPW-OWOJBTEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological role
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 LocationsNot Available
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 IDFDB023160
KNApSAcK IDNot Available
Chemspider ID4825947
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkT-HCA
METLIN IDNot Available
PubChem Compound6155526
PDB IDNot Available
ChEBI ID553775
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niwa T, Maeda K, Asada H, Shibata M, Ohki T, Saito A, Furukawa H: Gas chromatographic-mass spectrometric analysis of organic acids in renal tissue biopsy: identification of 4-hydroxybutyric acid and 4-hydroxy-2-butenoic acid. J Chromatogr. 1982 Jun 11;230(1):1-6. [PubMed:7107749 ]
  2. Niwa T, Yamamoto N, Asada H, Kawanishi A, Yokoyama M, Maeda K, Ohki T: Ischemic change of organic acids in kidney. J Chromatogr. 1983 Feb 11;272(2):227-32. [PubMed:6833421 ]