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Showing NP-Card for (cis)-crotonaldehyde (NP0336556)

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Record Information
Version2.0
Created at2024-09-11 06:50:43 UTC
Updated at2024-09-11 06:50:44 UTC
NP-MRD IDNP0336556
Secondary Accession NumbersNone
Natural Product Identification
Common Name(cis)-crotonaldehyde
Description(E)-2-Butenal, also known as (2E)-but-2-enal or crotonal, 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 (E)-2-Butenal is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (E)-2-Butenal has been detected, but not quantified in, several different foods, such as cottonseeds, mexican groundcherries, lemon balms, kumquats, and nances. (cis)-crotonaldehyde was first documented in 2012 (PMID: 22354192). This could make (e)-2-butenal a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336556 ((cis)-crotonaldehyde)


  Mrv0541 05061307402D          

  5  4  0  0  0  0            999 V2000
    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
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
M  END
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3D MOL for NP0336556 ((cis)-crotonaldehyde)

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3D SDF for NP0336556 ((cis)-crotonaldehyde)

  Mrv0541 05061307402D          

  5  4  0  0  0  0            999 V2000
    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
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0336556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2-

> <INCHI_KEY>
MLUCVPSAIODCQM-IHWYPQMZSA-N

> <FORMULA>
C4H6O

> <MOLECULAR_WEIGHT>
70.0898

> <EXACT_MASS>
70.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
7.522974242032385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-but-2-enal

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
0.7609660349999998

> <ALOGPS_LOGS>
-0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.090822229263441

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
22.0395

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
crotonaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0336556 ((cis)-crotonaldehyde)
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PDB for NP0336556 ((cis)-crotonaldehyde)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.310  -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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  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                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END

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3D PDB for NP0336556 ((cis)-crotonaldehyde)
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SMILES for NP0336556 ((cis)-crotonaldehyde)
C\C=C/C=O
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INCHI for NP0336556 ((cis)-crotonaldehyde)
InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2-
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View in JSmol
Synonyms
ValueSource
(2E)-2-ButenalHMDB
(2E)-But-2-enalHMDB
(2Z)-2-ButenalHMDB
(cis)-CrotonaldehydeHMDB
(e)-But-2-enalHMDB
(e)-CrotonaldehydeHMDB
(e)-Crotonaldehyde (iupac)HMDB
(Z)-2-ButenalHMDB
(Z)-CrotonaldehydeHMDB
1-FormylpropeneHMDB
2-ButenalHMDB
2-BUTENAL (trans) crotonaldehydeHMDB
2-Butenal, inhibitedHMDB
2-Butenal, mixture OF cis and transHMDB
2-ButenaldehydeHMDB
3-Methylacrolein, inhibitedHMDB
Aldehyde crotoniqueHMDB
beta-Methyl acroleinHMDB
beta-MethylacroleinHMDB
But-(e)-2-enalHMDB
But-2-enalHMDB
cis-CrotonaldehydeHMDB
CRDHMDB
CrotenaldehydeHMDB
CrotonalHMDB
CrotonaldehydeHMDB
Crotonaldehyde, inhibitedHMDB
Crotonaldehyde, mixture OF cis and transHMDB
Crotonaldehyde, predominantly transHMDB
Crotonaldehyde, stabilizedHMDB
Crotonic aldehydeHMDB
CrotylaldehydeHMDB
e-2-ButenalHMDB
KrotonaldehydHMDB
MethylpropenalHMDB
Nchem.215-comp8HMDB
t-2-ButenalHMDB
TopanelHMDB
Topanel caHMDB
trans- CrotonalHMDB
trans-2-ButenalHMDB
trans-CrotonaldehydeHMDB
Chemical FormulaC4H6O
Average Mass70.0898 Da
Monoisotopic Mass70.04186 Da
IUPAC Name(2Z)-but-2-enal
Traditional Namecrotonaldehyde
CAS Registry NumberNot Available
SMILES
C\C=C/C=O
InChI Identifier
InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2-
InChI KeyMLUCVPSAIODCQM-IHWYPQMZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • Aldehyde
    • 

  • 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
logP0.88ALOGPS
logP0.76ChemAxon
logS-0.02ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.04 m³·mol⁻¹ChemAxon
Polarizability7.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034233  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030138  
KNApSAcK IDNot Available
Chemspider ID559039  
KEGG Compound IDNot Available
BioCyc IDCPD-7600  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound643950  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mori Y, Yamada S: Contribution of cation-pi interactions in iminium catalysis. Molecules. 2012 Feb 21;17(2):2161-8. doi: 10.3390/molecules17022161. [PubMed:22354192  ]