NP-MRD: Showing NP-Card for Methyl sinapate (NP0002806)

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Record Information

Version

1.0

Created at

2020-11-23 19:40:54 UTC

Updated at

2021-08-12 19:52:12 UTC

NP-MRD ID

NP0002806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl sinapate

Provided By

BMRB

Description

Methyl sinapate is found in Brassica carinata, Brassica juncea, Brassica nigra, Buxus papillosa, Elaeagnus lanceolata, Wasabia japonica , Fagraea gracilipes, Goniothalamus laoticus, Guatteria foliosa, Polygala vulgaris, Raphanus sativus, Solanum nigrum and Zanthoxylum piperitum. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.6169    0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1793    0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0897   -0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4378   -1.6276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6521    0.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626   -0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -0.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2231    1.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607    1.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088    3.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464    3.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7503    0.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1879    0.9410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4022   -0.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -1.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437   -3.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646   -1.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0450    1.8720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888   -1.0033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0545    0.0063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3041    1.7186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106   -2.2304    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8665    2.1467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0183    4.8687    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8745    1.9934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8840    3.8591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774   -0.0899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027   -3.7842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846   -3.0881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956   -4.8952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.8333    0.0000 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  7  1  0
  1 18  1  1
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
 11 24  1  1
 11 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  1
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END

NP0002806
     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    5.4791    0.9781   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730    0.6919   -0.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900   -0.5858   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596   -1.5755   -0.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341   -0.8370   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2907    0.1731    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    0.0467    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    1.2081    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3109    1.1559    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246    2.3319    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3608    3.5805    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -0.0512    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665   -0.1291    0.1410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736   -1.1894    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -2.4161    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1137   -3.6138   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064   -1.1747    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009    0.8789   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9739    0.3150    0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    2.0289    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -1.8483   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    1.1567    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990    2.1488    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019    3.6613   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1113    4.3650    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024    3.7303    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7875   -1.0477    0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8506   -4.4427    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196   -3.7706   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -3.6762    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144   -2.0928   -0.0263 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END


     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.6169    0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1793    0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0897   -0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4378   -1.6276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6521    0.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626   -0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -0.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2231    1.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607    1.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088    3.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464    3.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7503    0.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1879    0.9410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4022   -0.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -1.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437   -3.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646   -1.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0450    1.8720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888   -1.0033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0545    0.0063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3041    1.7186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106   -2.2304    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8665    2.1467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0183    4.8687    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8745    1.9934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8840    3.8591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774   -0.0899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027   -3.7842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846   -3.0881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956   -4.8952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.8333    0.0000 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  7  1  0
  1 18  1  1
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
 11 24  1  1
 11 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  1
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END
> <DATABASE_ID>
NP0002806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)17-3)7-10(16-2)12(9)14/h4-7,14H,1-3H3/b5-4+

> <INCHI_KEY>
JHLPYWLKSLVYOI-SNAWJCMRSA-N

> <FORMULA>
C12H14O5

> <MOLECULAR_WEIGHT>
238.239

> <EXACT_MASS>
238.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.478532532303664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
1.8964057963333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.288824461067613

> <JCHEM_PKA_STRONGEST_BASIC>
-4.601964658115229

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
62.736300000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002806
     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    5.4791    0.9781   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730    0.6919   -0.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900   -0.5858   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596   -1.5755   -0.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341   -0.8370   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2907    0.1731    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    0.0467    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    1.2081    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3109    1.1559    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246    2.3319    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3608    3.5805    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -0.0512    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665   -0.1291    0.1410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736   -1.1894    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -2.4161    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1137   -3.6138   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064   -1.1747    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009    0.8789   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9739    0.3150    0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    2.0289    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -1.8483   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    1.1567    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990    2.1488    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019    3.6613   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1113    4.3650    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024    3.7303    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7875   -1.0477    0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8506   -4.4427    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196   -3.7706   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -3.6762    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144   -2.0928   -0.0263 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         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       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   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   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   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
HETATM   17  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    8    9                                                       
CONECT    7    8   10                                                       
CONECT    8    4    6    7                                                  
CONECT    9    6   12   15                                                  
CONECT   10    7   12   16                                                  
CONECT   11    5   13   17                                                  
CONECT   12    9   10   14                                                  
CONECT   13   11                                                            
CONECT   14   12                                                            
CONECT   15    1    9                                                       
CONECT   16    2   10                                                       
CONECT   17    3   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    NP0002806
HETATM    1  C1  UNL     1       5.479   0.978  -0.058  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.073   0.692  -0.034  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.590  -0.586  -0.066  1.00  0.00           C  
HETATM    4  O2  UNL     1       4.360  -1.576  -0.118  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.134  -0.837  -0.040  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.291   0.173   0.015  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.155   0.047   0.046  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.938   1.208   0.105  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.311   1.156   0.136  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.025   2.332   0.193  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.361   3.581   0.220  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.963  -0.051   0.110  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.366  -0.129   0.141  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.174  -1.189   0.052  1.00  0.00           C  
HETATM   15  O5  UNL     1      -2.834  -2.416   0.026  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.114  -3.614  -0.033  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.806  -1.175   0.020  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.801   0.879  -1.093  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.974   0.315   0.662  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.627   2.029   0.316  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.760  -1.848  -0.065  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.724   1.157   0.039  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.399   2.149   0.124  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.602   3.661  -0.599  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.111   4.365   0.025  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.802   3.730   1.169  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.787  -1.048   0.120  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.851  -4.443   0.138  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.720  -3.771  -1.056  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.280  -3.676   0.694  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.214  -2.093  -0.026  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8    8   17
CONECT    8    9   23
CONECT    9   10   12   12
CONECT   10   11
CONECT   11   24   25   26
CONECT   12   13   14
CONECT   13   27
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   28   29   30
CONECT   17   31
END

NP0002806
     RDKit          3D

31 31  0  0  0  0  0  0  0  0999 V2000
    5.4791    0.9781   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730    0.6919   -0.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900   -0.5858   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596   -1.5755   -0.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341   -0.8370   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2907    0.1731    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    0.0467    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    1.2081    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3109    1.1559    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246    2.3319    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3608    3.5805    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -0.0512    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665   -0.1291    0.1410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736   -1.1894    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -2.4161    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1137   -3.6138   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064   -1.1747    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009    0.8789   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9739    0.3150    0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    2.0289    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -1.8483   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    1.1567    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990    2.1488    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019    3.6613   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1113    4.3650    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024    3.7303    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7875   -1.0477    0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8506   -4.4427    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196   -3.7706   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -3.6762    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144   -2.0928   -0.0263 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	Generator
Methyl sinapic acid	Generator
Antithiamine factor	MeSH

Chemical Formula

C₁₂H₁₄O₅

Average Mass

238.2390 Da

Monoisotopic Mass

238.08412 Da

IUPAC Name

methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Traditional Name

methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)17-3)7-10(16-2)12(9)14/h4-7,14H,1-3H3/b5-4+

InChI Key

JHLPYWLKSLVYOI-SNAWJCMRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brassica carinata	LOTUS Database	35616633
Brassica carinata B line	KNApSAcK Database	22123792
Brassica carinata Y line	KNApSAcK Database	22123792
Brassica juncea	LOTUS Database	35616633
Brassica nigra	LOTUS Database	35616633
Buxus papillosa	LOTUS Database	35616633
Elaeagnus lanceolata	LOTUS Database	35616633
Eutrema japonicum	Plant	KNApSAcK
Fagraea gracilipes	LOTUS Database	35616633
Goniothalamus laoticus	LOTUS Database	35616633
Guatteria foliosa	LOTUS Database	35616633
Polygala vulgaris	LOTUS Database	35616633
Raphanus sativus	LOTUS Database	35616633
Solanum nigrum	LOTUS Database	35616633
Wasabia japonica	KNApSAcK Database	22123792
Zanthoxylum piperitum	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.9	ChemAxon
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.74 m³·mol⁻¹	ChemAxon
Polarizability	24.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034328

Chemspider ID

4479104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]

Showing NP-Card for Methyl sinapate (NP0002806)

MOL for NP0002806 (Methyl sinapate)

3D MOL for NP0002806 (Methyl sinapate)

3D SDF for NP0002806 (Methyl sinapate)

3D-SDF for NP0002806 (Methyl sinapate)

PDB for NP0002806 (Methyl sinapate)

3D PDB for NP0002806 (Methyl sinapate)

SMILES for NP0002806 (Methyl sinapate)

INCHI for NP0002806 (Methyl sinapate)

Structure for NP0002806 (Methyl sinapate)

3D Structure for NP0002806 (Methyl sinapate)