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Showing NP-Card for Dehydrozingerone (NP0084512)

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Record Information
Version2.0
Created at2022-04-29 05:13:59 UTC
Updated at2022-04-29 05:14:00 UTC
NP-MRD IDNP0084512
Secondary Accession NumbersNone
Natural Product Identification
Common NameDehydrozingerone
DescriptionDehydrozingerone, also known as vanillidene acetone or MMHSK, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Dehydrozingerone is found in Curcuma longa , Fibraurea tinctoria and Zingiber officinale . Dehydrozingerone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084512 (Dehydrozingerone)


  Mrv1572004251604272D          

 16 16  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
M  END
Download

3D MOL for NP0084512 (Dehydrozingerone)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    2.4631    2.6066    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406    1.3006    0.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770    0.1574    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913    0.1465    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0736   -1.0134    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3784   -1.0773    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314    0.0036   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5744   -0.1200   -0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085    1.0902   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -1.2416   -0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -2.2499    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756   -2.2567    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -1.0658    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735   -1.1651    0.3756 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5328    2.7394   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648    3.2809   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254    2.9744    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    1.0975    0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9164   -2.0219    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    1.0034   -0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3417    0.9432   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077    1.9485   -0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192    1.3556    0.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453   -3.1871    0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105   -3.2100    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606   -2.0388    0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 11  5  1  0
  7 20  1  0
  6 19  1  0
  4 18  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
 14 26  1  0
 12 25  1  0
 11 24  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
Download

3D SDF for NP0084512 (Dehydrozingerone)


  Mrv1572004251604272D          

 16 16  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084512

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC(OC)=C(O)C=C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+

> <INCHI_KEY>
AFWKBSMFXWNGRE-ONEGZZNKSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.214

> <EXACT_MASS>
192.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.44360148172923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.004475195333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.685292811017217

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.511486304450656

> <JCHEM_PKA_STRONGEST_BASIC>
-4.528898028268719

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
55.05510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dehydrozingerone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0084512 (Dehydrozingerone)

Download
PDB for NP0084512 (Dehydrozingerone)
HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       4.001  -2.310   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.000  -3.080   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3    4    8   15                                                  
CONECT    4    3    9   16                                                  
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8    1    3   12                                                  
CONECT    9    4    5    7                                                  
CONECT   10    6   11   13                                                  
CONECT   11    7   10   14                                                  
CONECT   12    8                                                            
CONECT   13   10                                                            
CONECT   14    2   11                                                       
CONECT   15    3                                                            
CONECT   16    4                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0084512 (Dehydrozingerone)
Download
SMILES for NP0084512 (Dehydrozingerone)
[H]\C(=C(\[H])C1=CC(OC)=C(O)C=C1)C(C)=O
Download
INCHI for NP0084512 (Dehydrozingerone)
InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+
Download
View in JSmol
Synonyms
ValueSource
4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneMeSH
Vanillidene acetoneMeSH
DehydrozingerolMeSH
MMHSKMeSH
4-Hydroxy-3-methoxybenzalacetoneMeSH
Methyl-3-methoxy-4-hydroxystyryl ketoneMeSH
Methyl-3-methoxy-4-hydroxystyryl ketone, (e)-iosmerMeSH
DehydrozingeroneMeSH
Chemical FormulaC11H12O3
Average Mass192.2140 Da
Monoisotopic Mass192.07864 Da
IUPAC Name(3E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
Traditional Namedehydrozingerone
CAS Registry NumberNot Available
SMILES
[H]\C(=C(\[H])C1=CC(OC)=C(O)C=C1)C(C)=O
InChI Identifier
InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+
InChI KeyAFWKBSMFXWNGRE-ONEGZZNKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Curcuma longaPlant
Fibraurea tinctoriaLOTUS Database
Zingiber officinalePlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acids and derivatives  
Alternative Parents
Substituents
  • Hydroxycinnamic acid or derivatives
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Styrene
    • 

  • Methoxybenzene
    • 

  • Anisole
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Enone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Acryloyl-group
    • 

  • Ketone
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP2.17ALOGPS
logP2ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.06 m³·mol⁻¹ChemAxon
Polarizability20.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17840  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5354238  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available