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Showing NP-Card for (2e)-4-hydroxybut-2-enal (NP0328256)

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Record Information
Version2.0
Created at2022-09-12 11:34:15 UTC
Updated at2022-09-12 11:34:15 UTC
NP-MRD IDNP0328256
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-4-hydroxybut-2-enal
Description(E)-4-hydroxybut-2-enal, also known as penitricin b or 4-hydroxycrotonaldehyde, belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. (2e)-4-hydroxybut-2-enal is found in Talaromyces aculeatus. (2e)-4-hydroxybut-2-enal was first documented in 2012 (PMID: 22644472). Based on a literature review very few articles have been published on (E)-4-hydroxybut-2-enal.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0328256 ((2e)-4-hydroxybut-2-enal)


  Mrv1652309122213342D          

  6  5  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 O   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
    0.8250    0.0000    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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for NP0328256 ((2e)-4-hydroxybut-2-enal)

     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
    3.2650   -0.6766   -0.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463   -0.0122    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -0.5078   -0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257    0.2151    0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296   -0.2669    0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544    0.6663   -0.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915    0.9318    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349   -1.4511   -0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052    1.1811    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4789   -1.2456   -0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842   -0.3515    0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716    1.5174   -0.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  6 12  1  0
  5 10  1  0
  5 11  1  0
  4  9  1  0
  3  8  1  0
  2  7  1  0
M  END
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3D SDF for NP0328256 ((2e)-4-hydroxybut-2-enal)


  Mrv1652309122213342D          

  6  5  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 O   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
    0.8250    0.0000    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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328256

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O2/c5-3-1-2-4-6/h1-3,6H,4H2/b2-1+

> <INCHI_KEY>
FXCMZPXXCRHRNK-OWOJBTEDSA-N

> <FORMULA>
C4H6O2

> <MOLECULAR_WEIGHT>
86.09

> <EXACT_MASS>
86.036779433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.51424998797945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-hydroxybut-2-enal

> <JCHEM_LOGP>
-0.5198051216666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.597856465377006

> <JCHEM_PKA_STRONGEST_BASIC>
-2.537297582044098

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
23.814199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-hydroxybut-2-enal

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0328256 ((2e)-4-hydroxybut-2-enal)

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PDB for NP0328256 ((2e)-4-hydroxybut-2-enal)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   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       0.000  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    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 NP0328256 ((2e)-4-hydroxybut-2-enal)
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SMILES for NP0328256 ((2e)-4-hydroxybut-2-enal)
OC\C=C\C=O
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INCHI for NP0328256 ((2e)-4-hydroxybut-2-enal)
InChI=1S/C4H6O2/c5-3-1-2-4-6/h1-3,6H,4H2/b2-1+
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View in JSmol
Synonyms
ValueSource
Penitricin bMeSH
4-HydroxycrotonaldehydeMeSH
Chemical FormulaC4H6O2
Average Mass86.0900 Da
Monoisotopic Mass86.03678 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
OC\C=C\C=O
InChI Identifier
InChI=1S/C4H6O2/c5-3-1-2-4-6/h1-3,6H,4H2/b2-1+
InChI KeyFXCMZPXXCRHRNK-OWOJBTEDSA-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
Talaromyces aculeatusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentEnals  
Alternative Parents
Substituents
  • Enal
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Short-chain aldehyde
    • 

  • Primary alcohol
    • 

  • Aldehyde
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4945349  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6441134  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Akagawa K, Sugiyama M, Kudo K: Asymmetric Michael addition of boronic acids to a gamma-hydroxy-alpha,beta-unsaturated aldehyde catalyzed by resin-supported peptide. Org Biomol Chem. 2012 Jul 7;10(25):4839-43. doi: 10.1039/c2ob25431j. Epub 2012  May 29. [PubMed:22644472  ] 
  2. LOTUS database [Link]