MiMeDB: Showing metabocard for Sugar phosphate (MMDBc0031938)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:55:46 UTC

Update Date

2024-04-30 19:53:47 UTC

Metabolite ID

MMDBc0031938

Metabolite Identification

Common Name

Sugar phosphate

Description

Any monosaccharide containing an alcoholic hydroxy group esterified with phosphoric acid

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
 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


  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>
MMDBc0031938

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₆H₂₄NO₅

Average Mass

310.3655

Monoisotopic Mass

310.165447883

IUPAC Name

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

Traditional Name

sinapine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9340000000-63c6b1f491d1742f581e	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-07r9-9083000000-01fd82cd03199a2410f7	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ik9-0069000000-dae71e5c3cb5e8c98d01	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0090000000-689b623cad4015ad4305	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0kdi-0980000000-e85059fdfaf38b65fbf3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0092000000-57b6d7af206f0f8438e3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0090000000-c865ce6a2d45509c5636	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0090000000-c860008ae94305bdbb56	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0390000000-fe4aa244978824523259	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0kdj-0950000000-61508103ba9b618dbf8f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0090000000-bf3c90800cc09e89c513	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0090000000-e6a2d2e0e7afaaa89594	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0090000000-c17f367eb5b6d7c37692	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0090000000-4b0ecc4ed11995be1006	2017-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Seed	Armoracia rusticana	FooDB	31437929
Plant	Seed	Lepidium sativum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0029379

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

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Sugar phosphate (MMDBc0031938)

MOL for #<Metabolite:0x00007fecf128ea70>

3D MOL for #<Metabolite:0x00007fecf128ea70>

3D SDF for #<Metabolite:0x00007fecf128ea70>

3D-SDF for #<Metabolite:0x00007fecf128ea70>

PDB for #<Metabolite:0x00007fecf128ea70>

3D PDB for #<Metabolite:0x00007fecf128ea70>

SMILES for #<Metabolite:0x00007fecf128ea70>

INCHI for #<Metabolite:0x00007fecf128ea70>

Structure for #<Metabolite:0x00007fecf128ea70>

3D Structure for #<Metabolite:0x00007fecf128ea70>