NP-MRD: Showing NP-Card for (5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid (NP0204425)

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Record Information

Version

2.0

Created at

2022-09-05 00:05:42 UTC

Updated at

2022-09-05 00:05:42 UTC

NP-MRD ID

NP0204425

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

Description

4-O-Galloylshikimic acid, also known as 4-O-galloylshikimate, belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. (5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid is found in Quercus mongolica. Based on a literature review very few articles have been published on 4-O-Galloylshikimic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.9493    0.9444   -1.6984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4311    0.2406   -0.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2560   -0.2090    0.2140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0285   -0.1324   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410   -0.8787    0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0832   -1.1931    0.1492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6957   -1.8000    1.3174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    0.1385    0.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0403   -0.0362   -0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9225    0.3815    0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188    0.9622    1.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3454    0.1340    0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    0.5467    1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6155    0.3178    1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4960    0.7473    2.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -0.3290    0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4100   -0.5450    0.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1613   -0.7372   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240   -1.3925   -1.7705 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8145   -0.5069   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9124    0.9899   -1.0846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4497    2.2004   -0.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0524    0.3002   -1.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1523   -1.1641    0.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728   -1.2358    1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555   -1.8737   -0.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2668   -2.5266    1.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5484    0.6765    0.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653    1.0484    2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905    0.5856    2.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637   -1.0014   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838   -1.5840   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -0.8282   -1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502    1.3046   -1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9313    1.9285    0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104    0.9441   -2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6365   -0.6244   -2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 23  1  0
 23  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  8 21  1  0
 20 12  1  0
 22 35  1  0
 21 34  1  6
 23 36  1  0
 23 37  1  0
  5 25  1  0
  6 26  1  6
  7 27  1  0
  8 28  1  1
 13 29  1  0
 15 30  1  0
 17 31  1  0
 19 32  1  0
 20 33  1  0
  3 24  1  0
M  END


  Mrv1652309052202052D          

 23 24  0  0  1  0            999 V2000
    0.7145   -1.2375    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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 12 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  4 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC(=CC(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O9/c15-7-3-6(4-8(16)11(7)19)14(22)23-12-9(17)1-5(13(20)21)2-10(12)18/h1,3-4,9-10,12,15-19H,2H2,(H,20,21)/t9?,10-,12?/m1/s1

> <INCHI_KEY>
HISNMPXFHAULFP-SQLBVSGCSA-N

> <FORMULA>
C14H14O9

> <MOLECULAR_WEIGHT>
326.257

> <EXACT_MASS>
326.063782031

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.49029752851252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

> <JCHEM_LOGP>
-0.0554701933333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.103087487632585

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.492900491118842

> <JCHEM_PKA_STRONGEST_BASIC>
-3.239854178532827

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
74.72500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12                                                       
CONECT   21    8   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    4                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
4-O-Galloylshikimate	Generator

Chemical Formula

C₁₄H₁₄O₉

Average Mass

326.2570 Da

Monoisotopic Mass

326.06378 Da

IUPAC Name

(5R)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

Traditional Name

(5R)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(=CC(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C14H14O9/c15-7-3-6(4-8(16)11(7)19)14(22)23-12-9(17)1-5(13(20)21)2-10(12)18/h1,3-4,9-10,12,15-19H,2H2,(H,20,21)/t9?,10-,12?/m1/s1

InChI Key

HISNMPXFHAULFP-SQLBVSGCSA-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
Quercus mongolica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Cyclitol or derivatives
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Carboxylic acid
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	-0.055	ChemAxon
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.72 m³·mol⁻¹	ChemAxon
Polarizability	29.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

405512

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

460898

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid (NP0204425)

MOL for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D MOL for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D SDF for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D-SDF for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

PDB for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D PDB for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

SMILES for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

INCHI for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

Structure for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D Structure for NP0204425 ((5r)-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)