NP-MRD: Showing NP-Card for (2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid (NP0328756)

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Record Information

Version

2.0

Created at

2022-09-12 12:31:33 UTC

Updated at

2022-09-12 12:31:34 UTC

NP-MRD ID

NP0328756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid

Description

N-fumaryl-L-alanine dimethyl ester belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. (2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid is found in Penicillium chrysogenum. Based on a literature review very few articles have been published on N-fumaryl-L-alanine dimethyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122214312D          

 15 14  0  0  1  0            999 V2000
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  4  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C(O)=N[C@@H](C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO5/c1-6(9(13)15-3)10-7(11)4-5-8(12)14-2/h4-6H,1-3H3,(H,10,11)/b5-4+/t6-/m0/s1

> <INCHI_KEY>
AXLMQGRRCSKYDG-OVCGOVNKSA-N

> <FORMULA>
C9H13NO5

> <MOLECULAR_WEIGHT>
215.205

> <EXACT_MASS>
215.079372523

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.205206348144266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-4-methoxy-N-[(2S)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid

> <JCHEM_LOGP>
0.767292243666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.198485427287123

> <JCHEM_PKA_STRONGEST_BASIC>
1.4864850663553661

> <JCHEM_POLAR_SURFACE_AREA>
85.19000000000001

> <JCHEM_REFRACTIVITY>
51.964300000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-methoxy-N-[(2S)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.770  -4.001   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -5.335   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₃NO₅

Average Mass

215.2050 Da

Monoisotopic Mass

215.07937 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C(O)=N[C@@H](C)C(=O)OC

InChI Identifier

InChI=1S/C9H13NO5/c1-6(9(13)15-3)10-7(11)4-5-8(12)14-2/h4-6H,1-3H3,(H,10,11)/b5-4+/t6-/m0/s1

InChI Key

AXLMQGRRCSKYDG-OVCGOVNKSA-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
Penicillium chrysogenum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Alpha-amino acid ester
Alanine or derivatives
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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

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

71048829

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146684052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid (NP0328756)

MOL for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

3D MOL for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

3D SDF for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

3D-SDF for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

PDB for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

3D PDB for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

SMILES for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

INCHI for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

Structure for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)

3D Structure for NP0328756 ((2e)-4-methoxy-n-[(2s)-1-methoxy-1-oxopropan-2-yl]-4-oxobut-2-enimidic acid)