NP-MRD: Showing NP-Card for methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate (NP0330656)

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Record Information

Version

2.0

Created at

2022-09-12 16:13:00 UTC

Updated at

2022-09-12 16:13:00 UTC

NP-MRD ID

NP0330656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate

Description

Methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514462D          

 34 35  0  0  0  0            999 V2000
   12.2436    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9581    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6726    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3871    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1015    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8160    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5305    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2449    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9594    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6739    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3883    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1028    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.5318    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.9607    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4758    0.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2963    1.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1167    1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6688    2.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   25.0419    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.8427   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.7081   -0.6680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5963   -0.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6826    0.4561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2638   -0.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0174   -0.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.4876   -0.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  9 10  1  0  0  0  0
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 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 31 32  1  0  0  0  0
 21 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 79 80  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004161514462D          

 34 35  0  0  0  0            999 V2000
   12.2436    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9581    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6726    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1015    1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8160    1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 21 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC=CCCCC1(C)OC(=O)C(CN2C(CCC2=O)C(=O)OC)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H45NO6/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-19-27(2)24(30)21(25(31)34-27)20-28-22(26(32)33-3)17-18-23(28)29/h13-14,21-22,24,30H,4-12,15-20H2,1-3H3

> <INCHI_KEY>
RJWAXRBINWCTDA-UHFFFAOYSA-N

> <FORMULA>
C27H45NO6

> <MOLECULAR_WEIGHT>
479.658

> <EXACT_MASS>
479.324688173

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.82278893034201

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate

> <ALOGPS_LOGP>
5.93

> <JCHEM_LOGP>
5.128392844666667

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.46930489943026

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6146682625738875

> <JCHEM_POLAR_SURFACE_AREA>
93.14

> <JCHEM_REFRACTIVITY>
131.86769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.22e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      22.855   2.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.188   1.882   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.522   2.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.856   1.882   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.190   2.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.523   1.882   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.857   2.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.191   1.882   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.524   2.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.858   1.882   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.192   2.652   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.525   1.882   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.859   2.652   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.193   1.882   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      41.526   2.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.860   1.882   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.955   0.636   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      43.486   3.289   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      45.018   3.128   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      46.048   4.272   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      45.338   1.621   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.745   0.995   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      46.906  -0.537   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      48.240  -1.307   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      47.919  -2.813   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      46.388  -2.974   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      45.761  -1.567   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      44.255  -1.247   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      49.646  -0.680   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      49.807   0.851   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      50.892  -1.585   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      52.299  -0.959   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      44.004   0.851   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      43.843  -0.680   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   33                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23   28                                                  
CONECT   28   27                                                            
CONECT   29   24   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   21   16   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylic acid	Generator

Chemical Formula

C₂₇H₄₅NO₆

Average Mass

479.6580 Da

Monoisotopic Mass

479.32469 Da

IUPAC Name

methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate

Traditional Name

methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC=CCCCC1(C)OC(=O)C(CN2C(CCC2=O)C(=O)OC)C1O

InChI Identifier

InChI=1S/C27H45NO6/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-19-27(2)24(30)21(25(31)34-27)20-28-22(26(32)33-3)17-18-23(28)29/h13-14,21-22,24,30H,4-12,15-20H2,1-3H3

InChI Key

RJWAXRBINWCTDA-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Proline or derivatives
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyrrolidone
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidine
Methyl ester
Tetrahydrofuran
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	5.93	ALOGPS
logP	5.13	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.14 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	131.87 m³·mol⁻¹	ChemAxon
Polarizability	56.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate (NP0330656)

MOL for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

3D MOL for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

3D SDF for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

3D-SDF for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

PDB for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

3D PDB for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

SMILES for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

INCHI for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

Structure for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)

3D Structure for NP0330656 (methyl 1-{[4-hydroxy-5-methyl-2-oxo-5-(pentadec-4-en-1-yl)oxolan-3-yl]methyl}-5-oxopyrrolidine-2-carboxylate)