NP-MRD: Showing NP-Card for Sinapoyl-(S)-malate (NP0054928)

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Record Information

Version

2.0

Created at

2022-04-28 01:07:48 UTC

Updated at

2022-04-28 01:07:48 UTC

NP-MRD ID

NP0054928

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sinapoyl-(S)-malate

Description

Sinapic acid (S)-malate ester, also known as sinapoyl-(S)-malate, 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. Sinapoyl-(S)-malate is found in Arabidopsis thaliana, Brassica napus, Brassica rapa and Raphanus sativus. Based on a literature review very few articles have been published on sinapic acid (S)-malate ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
   -0.7805    3.3431    1.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538    2.2654    1.2179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5509    1.0540    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    0.9350    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.2499    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9387   -0.4144    0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7680    0.5434    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2165    0.2835    0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9790    1.2162    1.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6596   -0.9570    0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7032   -1.3507    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396   -1.2246    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4914   -2.2859   -0.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -3.5112   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354   -0.0272    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308    0.1601    0.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598    0.6128   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545    0.8380   -1.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506    0.8324   -0.6900 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2956    0.5131    0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -0.1768   -1.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7386   -0.0645   -1.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.7818   -1.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4256   -0.8881   -2.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    3.7227    0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    4.1732    1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3618    3.0986    2.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929    1.8304    1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -1.3778    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    1.5372    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3253   -1.4549   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1965   -2.2879   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522   -4.1885   -1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -4.0146    0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9291   -3.3930   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504    1.8716   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2914    1.2815    1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9999   -1.1844   -1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   -0.0059   -2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319   -1.8365   -2.4484 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 10  1  0
  8  9  2  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 15  3  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 19 36  1  6
 20 37  1  0
 21 38  1  0
 21 39  1  0
 24 40  1  0
M  END


  Mrv1652304282203072D          

 24 24  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  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
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054928

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC(=O)[C@@H](O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O9/c1-22-10-5-8(3-4-12(17)18)6-11(23-2)14(10)24-15(21)9(16)7-13(19)20/h3-6,9,16H,7H2,1-2H3,(H,17,18)(H,19,20)/b4-3+/t9-/m0/s1

> <INCHI_KEY>
SVOZVFTXNDIEBH-NWALNABHSA-N

> <FORMULA>
C15H16O9

> <MOLECULAR_WEIGHT>
340.284

> <EXACT_MASS>
340.079432095

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.808370080102044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-4-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2,6-dimethoxyphenoxy}-3-hydroxy-4-oxobutanoic acid

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.537708989333333

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.71189301462984

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.108362143327968

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9305230929971655

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
79.35019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sinapic acid (S)-malate ester

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    3   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
Sinapoyl-(S)-malate	ChEBI
Sinapoyl-(S)-malic acid	Generator
Sinapate (S)-malate ester	Generator
Sinapic acid (S)-malic acid ester	Generator

Chemical Formula

C₁₅H₁₆O₉

Average Mass

340.2840 Da

Monoisotopic Mass

340.07943 Da

IUPAC Name

(3S)-4-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2,6-dimethoxyphenoxy}-3-hydroxy-4-oxobutanoic acid

Traditional Name

sinapic acid (S)-malate ester

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC(=O)[C@@H](O)CC(O)=O

InChI Identifier

InChI=1S/C15H16O9/c1-22-10-5-8(3-4-12(17)18)6-11(23-2)14(10)24-15(21)9(16)7-13(19)20/h3-6,9,16H,7H2,1-2H3,(H,17,18)(H,19,20)/b4-3+/t9-/m0/s1

InChI Key

SVOZVFTXNDIEBH-NWALNABHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK
Brassica napus	LOTUS Database	35616633
Brassica rapa	LOTUS Database	35616633
Raphanus sativus	LOTUS Database	35616633

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

Cinnamic acid
Coumaric acid or derivatives
Phenol ester
Dimethoxybenzene
M-dimethoxybenzene
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Beta-hydroxy acid
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Hydroxy acid
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Ether
Carboxylic acid
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

malate ester (CHEBI:15596 )

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	0.97	ALOGPS
logP	0.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.11	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	79.35 m³·mol⁻¹	ChemAxon
Polarizability	31.81 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444177

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280548

PDB ID

Not Available

ChEBI ID

15596

Good Scents ID

Not Available

References

General References

Showing NP-Card for Sinapoyl-(S)-malate (NP0054928)

MOL for NP0054928 (Sinapoyl-(S)-malate)

3D MOL for NP0054928 (Sinapoyl-(S)-malate)

3D SDF for NP0054928 (Sinapoyl-(S)-malate)

3D-SDF for NP0054928 (Sinapoyl-(S)-malate)

PDB for NP0054928 (Sinapoyl-(S)-malate)

3D PDB for NP0054928 (Sinapoyl-(S)-malate)

SMILES for NP0054928 (Sinapoyl-(S)-malate)

INCHI for NP0054928 (Sinapoyl-(S)-malate)

Structure for NP0054928 (Sinapoyl-(S)-malate)

3D Structure for NP0054928 (Sinapoyl-(S)-malate)