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Showing NP-Card for (2e)-4-hydroxy-2-methylbut-2-enoic acid (NP0171669)

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Record Information
Version2.0
Created at2022-09-03 08:16:33 UTC
Updated at2022-09-03 08:16:34 UTC
NP-MRD IDNP0171669
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-4-hydroxy-2-methylbut-2-enoic acid
Description (2e)-4-hydroxy-2-methylbut-2-enoic acid is found in Artemisia aucheri. 4-Hydroxytiglic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)


  Mrv1652310101707122D          

  9  8  0  0  0  0            999 V2000
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
M  END
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3D MOL for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)

     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
    0.5385    0.7840    1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.2067    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557   -0.6683   -0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584   -0.2667    0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7402    0.2942   -0.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -0.6586   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7783   -1.5090   -1.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9614   -0.1620   -0.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5271    0.2299    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4869    1.3585    1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2656    1.5416    1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263   -1.4032   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622    0.4225    0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -1.1993    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882    0.6909   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    0.7521   -0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  3  2  2  0
  2  1  1  0
  2  6  1  0
  6  8  1  0
  6  7  2  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  8 16  1  0
M  END
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3D SDF for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)


  Mrv1652310101707122D          

  9  8  0  0  0  0            999 V2000
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CO)=C(\C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3/c1-4(2-3-6)5(7)8/h2,6H,3H2,1H3,(H,7,8)/b4-2+

> <INCHI_KEY>
NCQCQZXQBYAHBZ-DUXPYHPUSA-N

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.116

> <EXACT_MASS>
116.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.373847842303757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-hydroxy-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
0.0343616199999998

> <ALOGPS_LOGS>
0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.632682652840185

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.555295569286481

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5520408668096115

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
29.0967

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-hydroxy-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)

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PDB for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)
HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         0                                  
HETATM    1  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    3    4    9                                                  
CONECT    3    2    6                                                       
CONECT    4    1    2    5                                                  
CONECT    5    4    7    8                                                  
CONECT    6    3                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    2                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)
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SMILES for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)
[H]\C(CO)=C(\C)C(O)=O
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INCHI for NP0171669 ((2e)-4-hydroxy-2-methylbut-2-enoic acid)
InChI=1S/C5H8O3/c1-4(2-3-6)5(7)8/h2,6H,3H2,1H3,(H,7,8)/b4-2+
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Synonyms
ValueSource
4-HydroxytiglateGenerator
Chemical FormulaC5H8O3
Average Mass116.1160 Da
Monoisotopic Mass116.04734 Da
IUPAC Name(2E)-4-hydroxy-2-methylbut-2-enoic acid
Traditional Name(2E)-4-hydroxy-2-methylbut-2-enoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CO)=C(\C)C(O)=O
InChI Identifier
InChI=1S/C5H8O3/c1-4(2-3-6)5(7)8/h2,6H,3H2,1H3,(H,7,8)/b4-2+
InChI KeyNCQCQZXQBYAHBZ-DUXPYHPUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia aucheriLOTUS Database
Chemical Taxonomy
ClassificationNot classified
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-0.12ALOGPS
logP0.034ChemAxon
logS0.01ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.1 m³·mol⁻¹ChemAxon
Polarizability11.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0177210  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13855819  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]