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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:04 UTC

Update Date

2022-03-07 02:52:08 UTC

HMDB ID

HMDB0029379

Secondary Accession Numbers

HMDB29379

Metabolite Identification

Common Name

Sinapine

Description

Sinapine (CAS: 18696-26-9), also known as sinapoylcholine, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Sinapine is an extremely weak basic (essentially neutral) compound (based on its pKa). Sinapine has been detected, but not quantified, in garden cress and horseradish. Sinapine is found in brassicas. It is a storage protein isolated from the seeds of Brassica napus (rape). This could make sinapine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0029379
     RDKit          3D
Sinapine
 46 46  0  0  0  0  0  0  0  0999 V2000
    5.1638   -3.2063    0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6633   -1.9194    0.0531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -0.7970   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183   -0.9049   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747    0.1927   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317   -0.0045   -0.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    0.9811   -0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384    0.6978   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356    1.6417   -0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -0.5819   -0.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -0.9425   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -0.2157    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0169   -0.5642    0.5582 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6523    0.2180   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5077   -0.1553    1.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2274   -1.9711    0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    1.4301   -0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401    1.5645   -0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    2.8097   -0.7404 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3984    3.9334   -0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419    0.4478   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    0.6250   -0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3481   -3.3542   -0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038   -3.9896    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710   -3.3443    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318   -1.8603   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -1.0004   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7119    1.9980   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2714   -0.7359   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -2.0240   -0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -0.4569    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    0.8877    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1192    1.1955   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4276   -0.2901   -1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7325    0.3567   -0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1506    0.7340    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1080   -0.9506    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6892    0.0916    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4316   -2.5353    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2154    0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3424   -2.3137   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6704    2.3233   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    4.1047   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568    4.7916   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693    3.7832   -1.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2379    1.5253   -0.4251 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  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
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 13 14  1  0
 13 15  1  0
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  5 17  2  0
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 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
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 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
M  CHG  1  13   1
M  END


  Mrv1652304282020512D          

 22 22  0  0  0  0            999 V2000
 9999.268010000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.982410000.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.696110000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.411810000.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.696110001.7820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.125410000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.408010000.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8390 9998.4809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.841110000.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.691510000.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4080 9999.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1204 9998.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.554810000.9570    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10004.268410000.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.554810001.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.268410001.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.552810000.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.838410000.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.123810000.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1238 9999.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8383 9999.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5529 9999.7193    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  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
  1 17  1  0  0  0  0
 19  7  1  0  0  0  0
 21  8  1  0  0  0  0
 20 11  1  0  0  0  0
M  CHG  1  13   1
M  END
> <DATABASE_ID>
HMDB0029379

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1

> <INCHI_KEY>
HUJXHFRXWWGYQH-UHFFFAOYSA-O

> <FORMULA>
C16H24NO5

> <MOLECULAR_WEIGHT>
310.3655

> <EXACT_MASS>
310.165447883

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.32545227228419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
-0.93

> <JCHEM_LOGP>
-2.247286297805079

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.288740484436033

> <JCHEM_PKA_STRONGEST_BASIC>
-4.602090062685847

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
96.669

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sinapine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029379
     RDKit          3D
Sinapine
 46 46  0  0  0  0  0  0  0  0999 V2000
    5.1638   -3.2063    0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6633   -1.9194    0.0531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -0.7970   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183   -0.9049   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747    0.1927   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317   -0.0045   -0.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    0.9811   -0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384    0.6978   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356    1.6417   -0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -0.5819   -0.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -0.9425   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -0.2157    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0169   -0.5642    0.5582 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6523    0.2180   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5077   -0.1553    1.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2274   -1.9711    0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    1.4301   -0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401    1.5645   -0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    2.8097   -0.7404 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3984    3.9334   -0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419    0.4478   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    0.6250   -0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3481   -3.3542   -0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038   -3.9896    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710   -3.3443    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318   -1.8603   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -1.0004   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7119    1.9980   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2714   -0.7359   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -2.0240   -0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -0.4569    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    0.8877    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1192    1.1955   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4276   -0.2901   -1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7325    0.3567   -0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1506    0.7340    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1080   -0.9506    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6892    0.0916    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4316   -2.5353    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2154    0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3424   -2.3137   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6704    2.3233   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    4.1047   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568    4.7916   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693    3.7832   -1.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2379    1.5253   -0.4251 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  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
M  CHG  1  13   1
M  END

HEADER    PROTEIN                                 28-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-20         0                                  
HETATM    1  C   UNK     0    8665.3008668.453   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.6348667.683   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.9668668.453   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8669.3028667.683   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.9668669.993   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8670.6348668.453   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8659.9628668.453   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8662.6338663.831   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8671.9708667.683   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8658.6248667.679   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8659.9628665.371   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8661.2918663.059   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8673.3028668.453   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0    8674.6348667.683   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8673.3028670.274   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8674.6348669.223   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.9658667.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.6328668.453   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.2988667.683   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.2988666.143   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8662.6318665.373   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8663.9658666.143   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    6                                                       
CONECT    5    3                                                            
CONECT    6    4    9                                                       
CONECT    7   10   19                                                       
CONECT    8   12   21                                                       
CONECT    9    6   13                                                       
CONECT   10    7                                                            
CONECT   11   20                                                            
CONECT   12    8                                                            
CONECT   13    9   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   18   22    1                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20    7                                                  
CONECT   20   19   21   11                                                  
CONECT   21   20   22    8                                                  
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0029379
HETATM    1  C1  UNL     1       5.164  -3.206   0.236  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.663  -1.919   0.053  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.887  -0.797  -0.171  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.518  -0.905  -0.225  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.675   0.193  -0.448  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.232  -0.004  -0.492  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.390   0.981  -0.697  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.038   0.698  -0.726  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.836   1.642  -0.922  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.520  -0.582  -0.543  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.867  -0.943  -0.554  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.591  -0.216   0.530  1.00  0.00           C  
HETATM   13  N1  UNL     1      -5.017  -0.564   0.558  1.00  0.00           N1+
HETATM   14  C10 UNL     1      -5.652   0.218  -0.488  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.508  -0.155   1.870  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.227  -1.971   0.415  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.250   1.430  -0.619  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.640   1.564  -0.568  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.220   2.810  -0.740  1.00  0.00           O  
HETATM   20  C15 UNL     1       4.398   3.933  -0.967  1.00  0.00           C  
HETATM   21  C16 UNL     1       5.442   0.448  -0.344  1.00  0.00           C  
HETATM   22  O5  UNL     1       6.826   0.625  -0.300  1.00  0.00           O  
HETATM   23  H1  UNL     1       4.348  -3.354  -0.531  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.904  -3.990   0.077  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.671  -3.344   1.221  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.032  -1.860  -0.095  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.821  -1.000  -0.352  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.712   1.998  -0.845  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.271  -0.736  -1.567  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.947  -2.024  -0.357  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.107  -0.457   1.492  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.572   0.888   0.428  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.119   1.195  -0.522  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.428  -0.290  -1.451  1.00  0.00           H  
HETATM   35  H13 UNL     1      -6.733   0.357  -0.325  1.00  0.00           H  
HETATM   36  H14 UNL     1      -6.151   0.734   1.787  1.00  0.00           H  
HETATM   37  H15 UNL     1      -6.108  -0.951   2.348  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.689   0.092   2.560  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.432  -2.535   0.948  1.00  0.00           H  
HETATM   40  H18 UNL     1      -6.186  -2.215   0.959  1.00  0.00           H  
HETATM   41  H19 UNL     1      -5.342  -2.314  -0.630  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.670   2.323  -0.795  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.814   4.105  -0.040  1.00  0.00           H  
HETATM   44  H22 UNL     1       5.057   4.792  -1.150  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.769   3.783  -1.856  1.00  0.00           H  
HETATM   46  H24 UNL     1       7.238   1.525  -0.425  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6   17   17
CONECT    6    7    7   27
CONECT    7    8   28
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   15   16
CONECT   14   33   34   35
CONECT   15   36   37   38
CONECT   16   39   40   41
CONECT   17   18   42
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   43   44   45
CONECT   21   22
CONECT   22   46
END

HMDB0029379
     RDKit          3D
Sinapine
 46 46  0  0  0  0  0  0  0  0999 V2000
    5.1638   -3.2063    0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6633   -1.9194    0.0531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -0.7970   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183   -0.9049   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747    0.1927   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317   -0.0045   -0.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    0.9811   -0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384    0.6978   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356    1.6417   -0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -0.5819   -0.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -0.9425   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -0.2157    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0169   -0.5642    0.5582 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6523    0.2180   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5077   -0.1553    1.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2274   -1.9711    0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    1.4301   -0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401    1.5645   -0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    2.8097   -0.7404 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3984    3.9334   -0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419    0.4478   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    0.6250   -0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3481   -3.3542   -0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038   -3.9896    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710   -3.3443    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318   -1.8603   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -1.0004   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7119    1.9980   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2714   -0.7359   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -2.0240   -0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070   -0.4569    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    0.8877    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1192    1.1955   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4276   -0.2901   -1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7325    0.3567   -0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1506    0.7340    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1080   -0.9506    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6892    0.0916    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4316   -2.5353    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2154    0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3424   -2.3137   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6704    2.3233   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    4.1047   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568    4.7916   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693    3.7832   -1.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2379    1.5253   -0.4251 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  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
M  CHG  1  13   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(4-Hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminium	ChEBI
O-Sinapoylcholine	ChEBI
Sinapoylcholine	ChEBI
2-[[3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]oxy]-N,N,N- trimethylethanaminium, 9ci	HMDB
4-Hydroxy-3,5-dimethoxycinnamate choline	HMDB
Choline 4-hydroxy-3,5-dimethoxycinnamate, 8ci	HMDB
Sinapine bisulfate	HMDB
Sinapine bisulphate	HMDB
Sugar phosphoric acid	HMDB
trans-Sinapine	HMDB
trans-Sinapoylcholine	HMDB

Chemical Formula

C₁₆H₂₄NO₅

Average Molecular Weight

310.3655

Monoisotopic Molecular Weight

310.165447883

IUPAC Name

(2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium

Traditional Name

sinapine

CAS Registry Number

84123-22-8

SMILES

COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O

InChI Identifier

InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1

InChI Key

HUJXHFRXWWGYQH-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Acyl choline
Anisole
Methoxybenzene
Phenol ether
Styrene
Phenoxy compound
Fatty acid ester
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Enoate ester
Quaternary ammonium salt
Alpha,beta-unsaturated carboxylic ester
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic oxide
Organic salt
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acylcholine (CHEBI:16353 )
Sinapate derivatives (C00933 )
a small molecule (O-SINAPOYLCHOLINE )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6398 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-3.370 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	-2.2	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	96.67 m³·mol⁻¹	ChemAxon
Polarizability	34.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.572	31661259
DarkChem	[M-H]-	173.576	31661259
DeepCCS	[M+H]+	166.179	30932474
DeepCCS	[M-H]-	163.821	30932474
DeepCCS	[M-2H]-	197.755	30932474
DeepCCS	[M+Na]+	172.918	30932474
AllCCS	[M+H]+	173.5	32859911
AllCCS	[M+H-H2O]+	170.6	32859911
AllCCS	[M+NH4]+	176.2	32859911
AllCCS	[M+Na]+	177.0	32859911
AllCCS	[M-H]-	181.1	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	183.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.18 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3121 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.55 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1255.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	192.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	135.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	360.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	323.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	665.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	979.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	176.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1239.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	422.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	372.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sinapine	COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O	3883.7	Standard polar	33892256
Sinapine	COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O	2277.2	Standard non polar	33892256
Sinapine	COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O	2431.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sinapine,1TMS,isomer #1	COC1=CC(/C=C/C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2461.0	Semi standard non polar	33892256
Sinapine,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2710.5	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sinapine

METLIN ID

Not Available

PubChem Compound

89287

PDB ID

Not Available

ChEBI ID

16353

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1063401

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Sinapine (HMDB0029379)

MOL for HMDB0029379 (Sinapine)

3D MOL for HMDB0029379 (Sinapine)

3D SDF for HMDB0029379 (Sinapine)

3D-SDF for HMDB0029379 (Sinapine)

PDB for HMDB0029379 (Sinapine)

3D PDB for HMDB0029379 (Sinapine)

SMILES for HMDB0029379 (Sinapine)

INCHI for HMDB0029379 (Sinapine)

Structure for HMDB0029379 (Sinapine)

3D Structure for HMDB0029379 (Sinapine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized