Showing NP-Card for 4-Hydroxycrotonic acid (NP0087052)

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Record Information
Version2.0
Created at2022-05-11 16:38:34 UTC
Updated at2022-05-11 16:38:34 UTC
NP-MRD IDNP0087052
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxycrotonic acid
Description4-Hydroxycrotonic acid, also known as 4-hydroxy-2-butenoate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 4-Hydroxycrotonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It is an analogue of γ-hydroxybutyric acid (GHB), as well as an active metabolite of GHB. T-HCA binds to the high-affinity GHB receptor with 4-fold greater affinity than GHB itself, where it acts as an agonist, but does not bind to the low-affinity GHB binding site, the GABAB receptor. Because of this, T-HCA does not produce sedation, and instead causes convulsions, which are thought to be caused by GHB receptor activation-evoked increases in extracellular glutamate concentrations, with one notable area where this occurs being the hippocampus. 4-Hydroxycrotonic acid was first documented in 1982 (PMID: 7107749). Similarly to GHB, T-HCA has been found to be endogenous to the rat central nervous system, and as a metabolite of GHB, is almost certain to be endogenous to humans as well.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087052 (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
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3D MOL for NP0087052 (4-Hydroxycrotonic acid)

     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.2818   -1.1526    0.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -0.4243    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515    0.0232   -0.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806   -0.0302   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3775   -0.4580    0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -0.0608    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398    0.7447   -0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759    0.9847   -0.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321    0.6120   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572   -1.0920    1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629   -0.9323    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769    0.5543    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7047    1.2315   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  7 13  1  0
  6 11  1  0
  6 12  1  0
  5 10  1  0
  4  9  1  0
  3  8  1  0
M  END
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3D SDF for NP0087052 (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>
NP0087052

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0087052 (4-Hydroxycrotonic acid)

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PDB for NP0087052 (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

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3D PDB for NP0087052 (4-Hydroxycrotonic acid)
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SMILES for NP0087052 (4-Hydroxycrotonic acid)
OC\C=C\C(O)=O
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INCHI for NP0087052 (4-Hydroxycrotonic acid)
InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h1-2,5H,3H2,(H,6,7)/b2-1+
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Synonyms
ValueSource
4-HydroxycrotonateGenerator
trans-4-Hydroxycrotonic acidHMDB
trans-4-HydroxycrotonateHMDB
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)-isomerHMDB
4-Hydroxy-2-butenoic acid, (Z)-isomerHMDB
4-Hydroxy-2-butenoic acid, sodium salt, (e)-isomerHMDB
4-Hydroxy-crotonateHMDB
Chemical FormulaC4H6O3
Average Mass102.0886 Da
Monoisotopic Mass102.03169 Da
IUPAC Name(2E)-4-hydroxybut-2-enoic acid
Traditional Name4-hydroxycrotonic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.31ALOGPS
logP-0.36ChemAxon
logS0.36ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.74 m³·mol⁻¹ChemAxon
Polarizability9.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003381  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
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  ]