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Showing NP-Card for 8-O-4'-Diferulic acid (NP0340022)

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Record Information
Version2.0
Created at2024-09-12 01:03:20 UTC
Updated at2024-09-12 01:03:21 UTC
NP-MRD IDNP0340022
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-O-4'-Diferulic acid
Description8-O-4'-Diferulic acid, also known as 8-O-4'-diferulate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Based on a literature review very few articles have been published on 8-O-4'-Diferulic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0340022 (8-O-4'-Diferulic acid)

8-O-4-Diferulic acid
  Mrv1652304022019342D          

 28 29  0  0  0  0            999 V2000
    6.6994   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4139   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1284   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8428   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1284    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635   -2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6779   -1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6779   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -1.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -3.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2503   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359   -4.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  2  0  0  0  0
  3  2  1  0  0  0  0
  9  2  1  0  0  0  0
  4  3  2  0  0  0  0
  8  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
 10  9  1  0  0  0  0
  1 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 17 16  1  0  0  0  0
 23 16  1  0  0  0  0
 18 17  2  0  0  0  0
 22 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 24 23  1  0  0  0  0
 15 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 25  8  1  0  0  0  0
M  END
Download

3D MOL for NP0340022 (8-O-4'-Diferulic acid)

Download
3D SDF for NP0340022 (8-O-4'-Diferulic acid)
8-O-4-Diferulic acid
  Mrv1652304022019342D          

 28 29  0  0  0  0            999 V2000
    6.6994   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4139   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1284   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8428   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1284    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635   -2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6779   -1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6779   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -1.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -3.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2503   -3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359   -4.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  2  0  0  0  0
  3  2  1  0  0  0  0
  9  2  1  0  0  0  0
  4  3  2  0  0  0  0
  8  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
 10  9  1  0  0  0  0
  1 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 17 16  1  0  0  0  0
 23 16  1  0  0  0  0
 18 17  2  0  0  0  0
 22 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 24 23  1  0  0  0  0
 15 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 25  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0340022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C(/OC2=CC=C(\C=C\C(O)=O)C=C2OC)C(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O8/c1-26-16-10-13(3-6-14(16)21)11-18(20(24)25)28-15-7-4-12(5-8-19(22)23)9-17(15)27-2/h3-11,21H,1-2H3,(H,22,23)(H,24,25)/b8-5+,18-11-

> <INCHI_KEY>
GGCXWTMEZZGUFT-ZMCAKAGVSA-N

> <FORMULA>
C20H18O8

> <MOLECULAR_WEIGHT>
386.356

> <EXACT_MASS>
386.10016754

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.38885578413026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
2.9652136743333335

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.784849379184704

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9639589879059445

> <JCHEM_PKA_STRONGEST_BASIC>
-4.521159932169788

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
101.1964

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0340022 (8-O-4'-Diferulic acid)
Download
PDB for NP0340022 (8-O-4'-Diferulic acid)
HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 8-O-4-Diferulic acid                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      12.506  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.505  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.505  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.838  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.172  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.172  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.838  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.171  -3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       7.171  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.837  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.839  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.173  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.507  -1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      15.173   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.800  -6.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.799  -5.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.799  -4.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.132  -3.410   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.466  -4.180   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.466  -5.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.132  -6.490   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.465  -3.410   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.465  -6.490   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.869  -5.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.133  -5.720   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.467  -6.490   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.801  -5.720   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.467  -8.030   0.000  0.00  0.00           O+0
CONECT    1    6   11                                                       
CONECT    2    7    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    2    6                                                       
CONECT    8    3   25                                                       
CONECT    9    2   10                                                       
CONECT   10    9                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   20   25                                                       
CONECT   16   21   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   15   19   21                                                  
CONECT   21   16   20                                                       
CONECT   22   17                                                            
CONECT   23   16   24                                                       
CONECT   24   23                                                            
CONECT   25   15   26    8                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

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3D PDB for NP0340022 (8-O-4'-Diferulic acid)
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SMILES for NP0340022 (8-O-4'-Diferulic acid)
COC1=CC(\C=C(/OC2=CC=C(\C=C\C(O)=O)C=C2OC)C(O)=O)=CC=C1O
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INCHI for NP0340022 (8-O-4'-Diferulic acid)
InChI=1S/C20H18O8/c1-26-16-10-13(3-6-14(16)21)11-18(20(24)25)28-15-7-4-12(5-8-19(22)23)9-17(15)27-2/h3-11,21H,1-2H3,(H,22,23)(H,24,25)/b8-5+,18-11-
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View in JSmol
Synonyms
ValueSource
8-O-4'-DiferulateGenerator
(2Z)-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoateGenerator
Chemical FormulaC20H18O8
Average Mass386.3560 Da
Monoisotopic Mass386.10017 Da
IUPAC Name(2Z)-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Traditional Name(2Z)-2-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C(/OC2=CC=C(\C=C\C(O)=O)C=C2OC)C(O)=O)=CC=C1O
InChI Identifier
InChI=1S/C20H18O8/c1-26-16-10-13(3-6-14(16)21)11-18(20(24)25)28-15-7-4-12(5-8-19(22)23)9-17(15)27-2/h3-11,21H,1-2H3,(H,22,23)(H,24,25)/b8-5+,18-11-
InChI KeyGGCXWTMEZZGUFT-ZMCAKAGVSA-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 phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassPhenylpyruvic acid derivatives  
Direct ParentPhenylpyruvic acid derivatives  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Cinnamic acid or derivatives
    • 

  • Coumaric acid or derivatives
    • 

  • Hydroxycinnamic acid
    • 

  • Hydroxycinnamic acid or derivatives
    • 

  • Enol-phenylpyruvate
    • 

  • Phenoxyacetate
    • 

  • Methoxyphenol
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Styrene
    • 

  • Anisole
    • 

  • Phenoxy compound
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP3.44ALOGPS
logP2.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.2 m³·mol⁻¹ChemAxon
Polarizability38.39 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB097219  
KNApSAcK IDNot Available
Chemspider ID8425026  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available