NP-MRD: Showing NP-Card for Sinapic acid (NP0000676)

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Record Information

Version

2.0

Created at

2012-09-11 17:50:48 UTC

Updated at

2024-09-03 04:22:49 UTC

NP-MRD ID

NP0000676

Natural Product DOI

https://doi.org/10.57994/2993

Secondary Accession Numbers

None

Natural Product 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 has been detected, but not quantified, in several different foods, such as strawberry guava, purple lavers, common verbena, ryes, and lupines. This could make sinapic acid a potential biomarker for the consumption of these foods. A sinapic acid in which the double bond has trans-configuration.

Structure

MOL SDF 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>
NP0000676

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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 Mass

224.2100 Da

Monoisotopic Mass

224.06847 Da

IUPAC Name

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

Traditional Name

sinapinic acid

CAS Registry Number

530-59-6

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Alliaria petiolata		LOTUS database
Allium cepa		LOTUS database
Althaea officinalis		LOTUS database
Arabidopsis thaliana	Plant	KNApSAcK
Avena sativa		LOTUS database
Betula pubescens		LOTUS database
Brassica carinata		LOTUS database
Brassica juncea		LOTUS database
Brassica napus		LOTUS database
Brassica oleracea		LOTUS database
Brassica rapa		LOTUS database
Calligonum leucocladum		LOTUS database
Cassia javanica		LOTUS database
Citrus aurantium		LOTUS database
Citrus limon		LOTUS database
Citrus sinensis		LOTUS database
Coffea canephora		LOTUS database
Cynanchum thesioides		LOTUS database
Cynanchum vincetoxicum		LOTUS database
Descurainia Sophia		LOTUS database
Eutrema japonicum	Plant	KNApSAcK
Ficaria verna		LOTUS database
Ginkgo biloba		LOTUS database
Glechoma hederacea		LOTUS database
Glycine max		LOTUS database
Hordeum vulgare		LOTUS database
Iris germanica		LOTUS database
Isatis tinctoria		LOTUS database
Isodon japonicus		LOTUS database
Juglans regia		LOTUS database
Limoniastrum guyonianum		LOTUS database
Linum usitatissimum		LOTUS database
Lithospermum erythrorhizon		LOTUS database
Lycopus europaeus		LOTUS database
Malus sylvestris		LOTUS database
Matthiola incana		LOTUS database
Menyanthes trifoliata		LOTUS database
Olea europaea		LOTUS database
Oxalis pes-caprae		LOTUS database
Panax ginseng		LOTUS database
Persea americana		LOTUS database
Persicaria lapathifolia		LOTUS database
Phaseolus vulgaris		LOTUS database
Poa huecu		LOTUS database
Posidonia oceanica		LOTUS database
Potentilla fruticosa		LOTUS database
Prunus cerasus		LOTUS database
Pterogyne nitens		LOTUS database
Rhaponticum carthamoides		LOTUS database
Secale cereale		LOTUS database
Secamone afzelii		LOTUS database
Sida acuta		LOTUS database
Sinapis alba		LOTUS database
Tecoma stans		LOTUS database
Triticum turgidum		LOTUS database
Vaccinium macrocarpon		LOTUS database
Vincetoxicum scandens		LOTUS database
Vitis vinifera		LOTUS database
Zea mays		LOTUS database

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	192 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted 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

External Links

HMDB ID

HMDB0032616

DrugBank ID

DB08587

Phenol Explorer Compound ID

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Chadni M, Flourat AL, Reungoat V, Mouterde LMM, Allais F, Ioannou I: Selective Extraction of Sinapic Acid Derivatives from Mustard Seed Meal by Acting on pH: Toward a High Antioxidant Activity Rich Extract. Molecules. 2021 Jan 3;26(1):212. doi: 10.3390/molecules26010212. [PubMed:33401641 ]
Qian B, Wang C, Zeng Z, Ren Y, Li D, Song JL: Ameliorative Effect of Sinapic Acid on Dextran Sodium Sulfate- (DSS-) Induced Ulcerative Colitis in Kunming (KM) Mice. Oxid Med Cell Longev. 2020 Nov 27;2020:8393504. doi: 10.1155/2020/8393504. eCollection 2020. [PubMed:33312339 ]
Verma V, Singh D, Kh R: Sinapic Acid Alleviates Oxidative Stress and Neuro-Inflammatory Changes in Sporadic Model of Alzheimer's Disease in Rats. Brain Sci. 2020 Nov 30;10(12):923. doi: 10.3390/brainsci10120923. [PubMed:33266113 ]
Hassan B, Tariq I A: Phenolic compounds and hepatoprotective potential of Anastatica hierochuntica ethanolic and aqueous extracts against CCl4-induced hepatotoxicity in rats. J Tradit Chin Med. 2020 Dec;40(6):947-955. doi: 10.19852/j.cnki.jtcm.2020.06.006. [PubMed:33258346 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Sinapic acid (NP0000676)

MOL for NP0000676 (Sinapic acid)

3D MOL for NP0000676 (Sinapic acid)

3D SDF for NP0000676 (Sinapic acid)

3D-SDF for NP0000676 (Sinapic acid)

PDB for NP0000676 (Sinapic acid)

3D PDB for NP0000676 (Sinapic acid)

SMILES for NP0000676 (Sinapic acid)

INCHI for NP0000676 (Sinapic acid)

Structure for NP0000676 (Sinapic acid)

3D Structure for NP0000676 (Sinapic acid)