NP-MRD: Showing NP-Card for 3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid (NP0289839)

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Record Information

Version

2.0

Created at

2022-09-09 20:13:27 UTC

Updated at

2022-09-09 20:13:27 UTC

NP-MRD ID

NP0289839

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid

Description

3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid is found in Chondria armata.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
    0.2257   -2.6498    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -1.1851    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637   -0.5374    0.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5652    0.8892    0.3878 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3549    1.2351    1.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6426    0.7183    1.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5175    0.7476    2.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7449    0.1763   -0.0052 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1115    0.2952   -0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6897    1.0415   -0.6828 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0686    2.3383   -0.8246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -0.4040   -0.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0323   -1.5164   -0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3958   -1.8721    0.5593 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6750   -0.5389    1.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0979   -0.3822    1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -0.4795    2.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -0.0924   -0.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    0.3777    0.5236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1944    1.7177    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1912    2.0295   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    2.7982   -0.3485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3387    1.6896   -2.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478   -3.2734   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2600   -2.8770    1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602   -3.0282   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437   -1.2009    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    1.5964    0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671   -0.8553   -0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428   -0.7490   -0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7849    1.0138   -0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    0.4416   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766    0.5561   -1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419    2.4766   -1.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6988    0.1419   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6863   -2.2800   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8524   -0.9901   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0183   -2.5358    1.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3612   -0.7331    2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1193   -0.9597   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9194    0.5671    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1714    2.4337    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    2.1804   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305    1.6787   -2.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
 10  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
  6  8  1  0
 19 12  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
  8 29  1  1
 10 33  1  6
 11 34  1  0
  4 28  1  6
  3 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 12 35  1  6
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  1
 19 41  1  1
 20 42  1  0
 20 43  1  0
 23 44  1  0
 18 40  1  0
M  END


  Mrv1652309092222132D          

 23 24  0  0  0  0            999 V2000
   -1.7204    1.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    0.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0059    0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0059   -0.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3385   -1.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5934   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085   -2.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033   -2.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733   -1.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -1.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211   -0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3280   -0.8004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7405   -0.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610    0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0459   -0.6672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966    0.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1885    0.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3600    1.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    1.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7578    1.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3162    2.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289839

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)C(OC1=O)\C=C(\C)C1CNC(C1CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO7/c1-6(3-10-13(19)7(2)15(22)23-10)9-5-16-12(14(20)21)8(9)4-11(17)18/h3,7-10,12-13,16,19H,4-5H2,1-2H3,(H,17,18)(H,20,21)/b6-3-

> <INCHI_KEY>
QAPZTOGRKYULRD-UTCJRWHESA-N

> <FORMULA>
C15H21NO7

> <MOLECULAR_WEIGHT>
327.333

> <EXACT_MASS>
327.13180202

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.87242756358367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(carboxymethyl)-4-[(1Z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid

> <JCHEM_LOGP>
-2.9170935481983657

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.047503561576062

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3482457970184072

> <JCHEM_PKA_STRONGEST_BASIC>
11.58670373685705

> <JCHEM_POLAR_SURFACE_AREA>
133.16

> <JCHEM_REFRACTIVITY>
77.1482

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(carboxymethyl)-4-[(1Z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.211   2.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.211   1.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.878   0.358   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.878  -1.182   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.632  -2.088   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.108  -3.552   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.202  -4.798   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.648  -3.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.553  -4.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.124  -2.088   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.664  -2.088   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.545   0.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.706  -1.174   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -6.212  -1.494   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -6.982  -0.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.514   0.001   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.419  -1.245   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -9.140   1.407   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.952   0.984   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.272   2.490   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.737   2.966   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.881   1.936   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -8.057   4.473   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    2   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₁NO₇

Average Mass

327.3330 Da

Monoisotopic Mass

327.13180 Da

IUPAC Name

3-(carboxymethyl)-4-[(1Z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid

Traditional Name

3-(carboxymethyl)-4-[(1Z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1C(O)C(OC1=O)\C=C(\C)C1CNC(C1CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C15H21NO7/c1-6(3-10-13(19)7(2)15(22)23-10)9-5-16-12(14(20)21)8(9)4-11(17)18/h3,7-10,12-13,16,19H,4-5H2,1-2H3,(H,17,18)(H,20,21)/b6-3-

InChI Key

QAPZTOGRKYULRD-UTCJRWHESA-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
Chondria armata	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	-2.9	ChemAxon
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	11.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.15 m³·mol⁻¹	ChemAxon
Polarizability	31.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid (NP0289839)

MOL for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

3D MOL for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

3D SDF for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

3D-SDF for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

PDB for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

3D PDB for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

SMILES for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

INCHI for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

Structure for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)

3D Structure for NP0289839 (3-(carboxymethyl)-4-[(1z)-1-(3-hydroxy-4-methyl-5-oxooxolan-2-yl)prop-1-en-2-yl]pyrrolidine-2-carboxylic acid)