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Showing NP-Card for Dihydrosinapic acid (NP0339448)

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Record Information
Version2.0
Created at2024-09-11 21:54:37 UTC
Updated at2024-09-11 21:54:37 UTC
NP-MRD IDNP0339448
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrosinapic acid
DescriptionDihydrosinapic acid, also known as dihydrosinapate or hdmpa CPD, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Dihydrosinapic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrosinapic acid is a metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339448 (Dihydrosinapic acid)


  Mrv1652306131922572D          

 16 16  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -2.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -2.9776    0.0000 C   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  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4 12  1  0  0  0  0
  3 13  1  0  0  0  0
  5 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
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3D MOL for NP0339448 (Dihydrosinapic acid)

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3D SDF for NP0339448 (Dihydrosinapic acid)

  Mrv1652306131922572D          

 16 16  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -2.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -2.9776    0.0000 C   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  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4 12  1  0  0  0  0
  3 13  1  0  0  0  0
  5 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCC(O)=O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h5-6,14H,3-4H2,1-2H3,(H,12,13)

> <INCHI_KEY>
BPPVOXVSMSXBEI-UHFFFAOYSA-N

> <FORMULA>
C11H14O5

> <MOLECULAR_WEIGHT>
226.2259

> <EXACT_MASS>
226.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.737556040307595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3,5-dimethoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
1.4366549173333334

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.340881769266202

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.772429754231048

> <JCHEM_PKA_STRONGEST_BASIC>
-4.602923868376613

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
56.873900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-hydroxy-3,5-dimethoxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339448 (Dihydrosinapic acid)
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PDB for NP0339448 (Dihydrosinapic acid)
HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.293  -0.938   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -7.042  -3.248   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -7.042  -0.168   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -4.375  -4.788   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -8.376  -0.938   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.709  -5.558   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9   10   11    8                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4                                                            
CONECT   13    3   15                                                       
CONECT   14    5   16                                                       
CONECT   15   13                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0339448 (Dihydrosinapic acid)
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SMILES for NP0339448 (Dihydrosinapic acid)
COC1=CC(CCC(O)=O)=CC(OC)=C1O
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INCHI for NP0339448 (Dihydrosinapic acid)
InChI=1S/C11H14O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h5-6,14H,3-4H2,1-2H3,(H,12,13)
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Synonyms
ValueSource
DihydrosinapateGenerator
HDMPA CPDHMDB
3-(4'-Hydroxyl-3',5'-dimethoxyphenyl)propionic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)propanoateHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)propionic acidHMDB
4-Hydroxy-3,5-dimethoxybenzenepropanoic acidHMDB
4-Hydroxy-3,5-dimethoxyhydrocinnamic acidHMDB
Dihydrosinapic acidHMDB
Chemical FormulaC11H14O5
Average Mass226.2259 Da
Monoisotopic Mass226.08412 Da
IUPAC Name3-(4-hydroxy-3,5-dimethoxyphenyl)propanoic acid
Traditional Name3-(4-hydroxy-3,5-dimethoxyphenyl)propanoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(CCC(O)=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C11H14O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h5-6,14H,3-4H2,1-2H3,(H,12,13)
InChI KeyBPPVOXVSMSXBEI-UHFFFAOYSA-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 phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassPhenylpropanoic acids  
Sub ClassNot Available
Direct ParentPhenylpropanoic acids  
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
    • 

  • Methoxyphenol
    • 

  • Dimethoxybenzene
    • 

  • M-dimethoxybenzene
    • 

  • Anisole
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Methoxybenzene
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.08ALOGPS
logP1.44ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.87 m³·mol⁻¹ChemAxon
Polarizability22.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041727  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029893  
KNApSAcK IDNot Available
Chemspider ID76391  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound84681  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References