NP-MRD: Showing NP-Card for (z)-sinapic acid (NP0253907)

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Record Information

Version

2.0

Created at

2022-09-07 17:55:11 UTC

Updated at

2022-09-07 17:55:11 UTC

NP-MRD ID

NP0253907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(z)-sinapic acid

Description

Cis-Sinapic acid, also known as cis-sinapate or synapitic acid, 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. Cis-Sinapic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cis-Sinapic acid has been detected, but not quantified in, common pea and pulses. This could make cis-sinapic acid a potential biomarker for the consumption of these foods. (z)-sinapic acid is found in Arabidopsis thaliana, Brassica napus, Gliricidia sepium, Secale cereale and Zea mays. A 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid in which the double bond has cis-configuration.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306171921402D          

 16 16  0  0  0  0            999 V2000
10000.428610000.1764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7133 9999.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.004310000.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.004310002.6394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.291110002.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.849510002.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.670710002.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.381010002.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.093310002.6394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.381010001.4098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.141810002.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.427310002.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.712610002.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.712610001.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.427210000.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.141810001.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  1 15  1  0  0  0  0
 14  3  1  0  0  0  0
 13  4  1  0  0  0  0
 11  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253907

> <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-ARJAWSKDSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.21

> <EXACT_MASS>
224.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.809927608666506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-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>
9.405617577384861

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.106694924305161

> <JCHEM_PKA_STRONGEST_BASIC>
-4.604716715085129

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
57.96720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic 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  O   UNK     0    8667.4678666.996   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8666.1318666.228   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8664.8088668.529   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8664.8088671.594   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8663.4778670.827   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.1198671.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.6528671.594   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.9788670.831   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8674.3088671.594   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8672.9788669.298   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8668.7988670.834   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.4648671.604   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.1308670.833   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.1308669.293   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.4648668.523   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.7988669.293   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1                                                            
CONECT    3   14                                                            
CONECT    4    5   13                                                       
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12   16    6                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14    4                                                  
CONECT   14   13   15    3                                                  
CONECT   15   14   16    1                                                  
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(Z)-4-Hydroxy-3,5-dimethoxycinnamic acid	ChEBI
cis-4-Hydroxy-3,5-dimethoxycinnamic acid	ChEBI
(Z)-4-Hydroxy-3,5-dimethoxycinnamate	Generator
cis-4-Hydroxy-3,5-dimethoxycinnamate	Generator
cis-Sinapate	Generator
trans-Sinapinic acid	HMDB
3,5-Dimethoxy-4-hydroxycinnamic acid	HMDB
(e)-Sinapic acid	HMDB
Sinapic acid	HMDB
Sinapinic acid	HMDB
Synapitic acid	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid	HMDB
trans-Sinapic acid	HMDB
(2Z)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
(Z)-3,5-Dimethoxy-4-hydroxycinnamic acid	HMDB
(Z)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
(Z)-Sinapic acid	HMDB
3,5-Dimethoxy-4-hydroxy-cis-cinnamic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
Z-Sinapinic acid	HMDB
cis-Sinapinic acid	HMDB
cis-Sinapic acid	HMDB

Chemical Formula

C₁₁H₁₂O₅

Average Mass

224.2100 Da

Monoisotopic Mass

224.06847 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

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-ARJAWSKDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633
Brassica napus	LOTUS Database	35616633
Gliricidia sepium	LOTUS Database	35616633
Secale cereale	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

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:76350 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.63	ALOGPS
logP	1.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.11	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	21.81 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

HMDB0034069

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012318

KNApSAcK ID

Not Available

Chemspider ID

1266059

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1549091

PDB ID

Not Available

ChEBI ID

76350

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (z)-sinapic acid (NP0253907)

MOL for NP0253907 ((z)-sinapic acid)

3D MOL for NP0253907 ((z)-sinapic acid)

3D SDF for NP0253907 ((z)-sinapic acid)

3D-SDF for NP0253907 ((z)-sinapic acid)

PDB for NP0253907 ((z)-sinapic acid)

3D PDB for NP0253907 ((z)-sinapic acid)

SMILES for NP0253907 ((z)-sinapic acid)

INCHI for NP0253907 ((z)-sinapic acid)

Structure for NP0253907 ((z)-sinapic acid)

3D Structure for NP0253907 ((z)-sinapic acid)