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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:50:48 UTC

Update Date

2022-03-07 02:53:24 UTC

HMDB ID

HMDB0032616

Secondary Accession Numbers

HMDB32616

Metabolite Identification

Common Name

Sinapic acid

Description

Sinapic acid, also known as sinapinATE, 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. Sinapic acid is an odorless tasting compound. Sinapic acid is found, on average, in the highest concentration within a few different foods, such as sunflowers (Helianthus annuus), olives (Olea europaea), and garden onions (Allium cepa) and in a lower concentration in hard wheats (Triticum durum), rapes (Brassica napus var. napus), and garlics (Allium sativum). Sinapic acid has also been detected, but not quantified in, several different foods, such as chives (Allium schoenoprasum), teffs (Eragrostis tef), celeriacs (Apium graveolens var. rapaceum), yardlong beans (Vigna unguiculata ssp. sesquipedalis), and pepper (c. pubescens). This could make sinapic acid a potential biomarker for the consumption of these foods. Sinapic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Sinapic acid.

Structure

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


  Mrv1652306171921372D          

 16 16  0  0  0  0            999 V2000
   -1.6293   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440   -1.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6293   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -0.5024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -1.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440   -2.5653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0585   -2.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3  7  1  0  0  0  0
  4 13  1  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032616

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(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)/b4-3+

> <INCHI_KEY>
PCMORTLOPMLEFB-ONEGZZNKSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.21

> <EXACT_MASS>
224.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.323224439789968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-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>
9.405618194181288

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.606694294741961

> <JCHEM_PKA_STRONGEST_BASIC>
-4.604716708653556

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
57.967200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sinapinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.043  -0.168   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.294  -0.938   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -7.043  -3.248   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.377  -0.938   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.375  -4.789   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.709  -5.558   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    1                                                       
CONECT    7    3   14                                                       
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    4                                                            
CONECT   14    7                                                            
CONECT   15    5   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0032616
HETATM    1  C1  UNL     1      -1.470   3.953  -0.140  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.193   2.751  -0.198  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.485   1.549  -0.144  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.111   1.516  -0.037  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.565   0.295   0.014  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.013   0.326   0.127  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.764  -0.756   0.184  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.222  -0.621   0.298  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.802   0.484   0.344  1.00  0.00           O  
HETATM   10  O3  UNL     1       5.003  -1.762   0.357  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.162  -0.871  -0.044  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.550  -0.873  -0.152  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.278  -2.032  -0.210  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.779  -3.325  -0.173  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.173   0.354  -0.199  1.00  0.00           C  
HETATM   16  O5  UNL     1      -3.568   0.344  -0.308  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.147   4.828  -0.100  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.827   3.990  -1.061  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.836   3.913   0.771  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.444   2.443   0.007  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.552   1.288   0.170  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.313  -1.738   0.148  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.646  -2.669   0.629  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.323  -1.840  -0.007  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.590  -3.983   0.258  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.439  -3.718  -1.151  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.922  -3.364   0.531  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.114  -0.480  -0.351  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   20
CONECT    5    6   11   11
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9    9   10
CONECT   10   23
CONECT   11   12   24
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   25   26   27
CONECT   15   16
CONECT   16   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	ChEBI
SINAPINATE	ChEBI
Sinapinic acid	ChEBI
3,5-Dimethoxy-4-hydroxycinnamic acid	Kegg
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoate	Generator
3,5-Dimethoxy-4-hydroxycinnamate	Generator
Sinapate	Generator
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(2E)-2-propenoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(e)-2-propenoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
4-Hydroxy-3,5-dimethoxy-(e)-cinnamic acid	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid	HMDB
trans-3,5-Dimethoxy-4-hydroxycinnamic acid	HMDB
Sinapic acid	ChEBI
trans-Sinapate	Generator, HMDB
(e)-Sinapic acid	MeSH, HMDB
Synapitic acid	MeSH, HMDB
trans-Sinapinic acid	MeSH, HMDB
(E)-3,5-Dimethoxy-4-hydroxycinnamic acid	HMDB
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
(E)-Sinapic acid	HMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid	HMDB
E-Sinapinic acid	HMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid	HMDB
trans-Sinapic acid	HMDB

Chemical Formula

C₁₁H₁₂O₅

Average Molecular Weight

224.21

Monoisotopic Molecular Weight

224.068473494

IUPAC Name

(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

Traditional Name

sinapinic acid

CAS Registry Number

7362-37-0

SMILES

COC1=CC(\C=C\C(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)/b4-3+

InChI Key

PCMORTLOPMLEFB-ONEGZZNKSA-N

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (CHEBI:15714 )
Sinapate derivatives (C00482 )

Ontology

Physiological effect

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 12771321)
Feces (PMID: 19573517)

Cellular substructure

Extracellular (HMDB: HMDB0032616)
Cytoplasm (HMDB: HMDB0032616)

Source

Exogenous

Exogenous (HMDB: HMDB0032616)

Fruit juice (FooDB: FOOD00763)

Distilled beverage

Liquor (FooDB: FOOD00616)

Alcoholic beverage

Red wine (HMDB: HMDB0032616)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Nuts (HMDB: HMDB0032616)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (HMDB: HMDB0032616)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Vegetables (HMDB: HMDB0032616)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Biscuit (FooDB: FOOD00274)
Breakfast cereal (FooDB: FOOD00270)
Pasta (FooDB: FOOD00273)
Whole grain cereal products (HMDB: HMDB0032616)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)
Bulgur (FooDB: FOOD00741)
Other cereal product (FooDB: FOOD00272)

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Cocoa and cocoa product

Cocoa product

Cocoa powder (FooDB: FOOD00685)

Cocoa and cocoa products (HMDB: HMDB0032616)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0032616)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Fat and oil

Olive oil (HMDB: HMDB0032616)

Legumes (HMDB: HMDB0032616)

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Endogenous

Endogenous (HMDB: HMDB0032616)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192 °C	Not Available
Boiling Point	403.41 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	7082 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.286 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.97 m³·mol⁻¹	ChemAxon
Polarizability	22.32 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	152.601	30932474
DeepCCS	[M-H]-	150.243	30932474
DeepCCS	[M-2H]-	183.729	30932474
DeepCCS	[M+Na]+	158.72	30932474
AllCCS	[M+H]+	149.6	32859911
AllCCS	[M+H-H2O]+	145.6	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	148.2	32859911
AllCCS	[M+Na-2H]-	148.6	32859911
AllCCS	[M+HCOO]-	149.1	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.	4.65 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3862 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1535.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	283.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	118.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	72.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	392.3 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	319.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	886.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	317.1 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	1003.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	444.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	265.4 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	61.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sinapic acid	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O	3815.2	Standard polar	33892256
Sinapic acid	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O	2004.3	Standard non polar	33892256
Sinapic acid	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O	2149.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sinapic acid,1TMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1O	2214.3	Semi standard non polar	33892256
Sinapic acid,1TMS,isomer #2	COC1=CC(/C=C/C(=O)O)=CC(OC)=C1O[Si](C)(C)C	2169.8	Semi standard non polar	33892256
Sinapic acid,2TMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2201.5	Semi standard non polar	33892256
Sinapic acid,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	2477.7	Semi standard non polar	33892256
Sinapic acid,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2451.1	Semi standard non polar	33892256
Sinapic acid,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2735.3	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 464	12771321	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 464	12592675	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 464	14733499	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB08587

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sinapinic_acid

METLIN ID

Not Available

PubChem Compound

637775

PDB ID

Not Available

ChEBI ID

15714

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1548161

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yun KJ, Koh DJ, Kim SH, Park SJ, Ryu JH, Kim DG, Lee JY, Lee KT: Anti-inflammatory effects of sinapic acid through the suppression of inducible nitric oxide synthase, cyclooxygase-2, and proinflammatory cytokines expressions via nuclear factor-kappaB inactivation. J Agric Food Chem. 2008 Nov 12;56(21):10265-72. doi: 10.1021/jf802095g. Epub 2008 Oct 9. [PubMed:18841975 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Sinapic acid (HMDB0032616)

MOL for HMDB0032616 (Sinapic acid)

3D MOL for HMDB0032616 (Sinapic acid)

3D SDF for HMDB0032616 (Sinapic acid)

3D-SDF for HMDB0032616 (Sinapic acid)

PDB for HMDB0032616 (Sinapic acid)

3D PDB for HMDB0032616 (Sinapic acid)

SMILES for HMDB0032616 (Sinapic acid)

INCHI for HMDB0032616 (Sinapic acid)

Structure for HMDB0032616 (Sinapic acid)

3D Structure for HMDB0032616 (Sinapic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized