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Showing NP-Card for sinapoyl alcohol (NP0330574)

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Record Information
Version2.0
Created at2022-09-12 16:03:16 UTC
Updated at2022-09-12 16:03:16 UTC
NP-MRD IDNP0330574
Secondary Accession NumbersNone
Natural Product Identification
Common Namesinapoyl alcohol
Description3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid, also known as 3,5-dimethoxy-4-hydroxycinnamic acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. sinapoyl alcohol is found in Arabidopsis thaliana, Avena sativa, Brassica juncea, Brassica napus, Citrus aurantium, Citrus limon, Citrus sinensis, Vincetoxicum hirundinaria, Fagopyrum esculentum, Glechoma hederacea, Isodon japonicus, Juglans regia, Lithospermum erythrorhizon, Olea europaea, Oxalis pes-caprae, Phaseolus vulgaris, Posidonia oceanica, Prunus avium, Pterogyne nitens, Sabia japonica, Secale cereale, Theobroma cacao, Triticum aestivum, Triticum turgidum, Vitis vinifera and Zea mays. 3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0330574 (sinapoyl alcohol)


  Mrv1652308201916402D          

 16 16  0  0  0  0            999 V2000
    2.1434   -1.2375    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
    0.7145    2.0625    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
    1.4289    0.8250    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    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  4 10  1  4  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15  8  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
Download

3D MOL for NP0330574 (sinapoyl alcohol)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -2.5338   -2.5480   -2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -1.5856   -1.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981   -0.8315   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835   -0.9920   -1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603   -0.2633   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967   -0.4815   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0448   -0.1516   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6398    0.5794    0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1310    1.1607    1.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885    0.7011    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    0.6475    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1868    0.8032    0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347    1.7392    1.8232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146    2.5417    2.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1752    0.0723    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4828    0.2514    0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888   -2.1979   -3.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068   -3.4649   -1.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -2.8849   -2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -1.7224   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9124   -1.1020   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791   -0.5660   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4811    0.9158   -0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824    1.2686    0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618    2.0365    3.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024    2.9887    1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930    3.3811    2.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1952   -0.2955    0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 16 28  1  0
M  END
Download

3D SDF for NP0330574 (sinapoyl alcohol)


  Mrv1652308201916402D          

 16 16  0  0  0  0            999 V2000
    2.1434   -1.2375    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
    0.7145    2.0625    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
    1.4289    0.8250    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    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  4 10  1  4  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15  8  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330574

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)

> <INCHI_KEY>
PCMORTLOPMLEFB-UHFFFAOYSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.212

> <EXACT_MASS>
224.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.222229710034018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.5171784069999998

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.40561872178323

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.806693764961078

> <JCHEM_PKA_STRONGEST_BASIC>
-4.604716707555859

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
57.96720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sinapoyl alcohol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0330574 (sinapoyl alcohol)

Download
PDB for NP0330574 (sinapoyl alcohol)
HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   6.930   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  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3    4    7                                                       
CONECT    4    3   10                                                       
CONECT    5    7    8                                                       
CONECT    6    7    9                                                       
CONECT    7    3    5    6                                                  
CONECT    8    5   11   15                                                  
CONECT    9    6   11   16                                                  
CONECT   10    4   12   13                                                  
CONECT   11    8    9   14                                                  
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    1    8                                                       
CONECT   16    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Download
3D PDB for NP0330574 (sinapoyl alcohol)
Download
SMILES for NP0330574 (sinapoyl alcohol)
COC1=CC(C=CC(O)=O)=CC(OC)=C1O
Download
INCHI for NP0330574 (sinapoyl alcohol)
InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)
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View in JSmol
Synonyms
ValueSource
3,5-Dimethoxy-4-hydroxycinnamic acidChEBI
3,5-Dimethoxy-4-hydroxycinnamateGenerator
3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoateGenerator
Sinapic acidChEBI, HMDB, MeSH
SinapateGenerator, HMDB
trans-Sinapic acidMeSH
trans-Sinapinic acidMeSH
Synapitic acidMeSH
(e)-Sinapic acidMeSH
Sinapinic acidMeSH
Chemical FormulaC11H12O5
Average Mass224.2120 Da
Monoisotopic Mass224.06847 Da
IUPAC Name3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
Traditional Namesinapoyl alcohol
CAS Registry NumberNot Available
SMILES
COC1=CC(C=CC(O)=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)
InChI KeyPCMORTLOPMLEFB-UHFFFAOYSA-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
Arabidopsis thalianaLOTUS Database
Avena sativaLOTUS Database
Brassica junceaLOTUS Database
Brassica napusLOTUS Database
Citrus aurantiumLOTUS Database
Citrus limonLOTUS Database
Citrus sinensisLOTUS Database
Cynanchum vincetoxicumLOTUS Database
Fagopyrum esculentumLOTUS Database
Glechoma hederaceaLOTUS Database
Isodon japonicusLOTUS Database
Juglans regiaLOTUS Database
Lithospermum erythrorhizonLOTUS Database
Olea europaeaLOTUS Database
Oxalis pes-capraeLOTUS Database
Phaseolus vulgarisLOTUS Database
Posidonia oceanicaLOTUS Database
Prunus aviumLOTUS Database
Pterogyne nitensLOTUS Database
Sabia japonicaLOTUS Database
Secale cerealeLOTUS Database
Theobroma cacaoLOTUS Database
Triticum aestivumLOTUS Database
Triticum turgidumLOTUS Database
Vitis viniferaLOTUS Database
Zea maysLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acids  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Coumaric acid or derivatives
    • 

  • Hydroxycinnamic acid
    • 

  • M-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Styrene
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.63ALOGPS
logP1.52ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.97 m³·mol⁻¹ChemAxon
Polarizability22.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0127488  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB086350  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSinapinic_acid  
METLIN IDNot Available
PubChem Compound10743  
PDB IDNot Available
ChEBI ID77131  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]