NP-MRD: Showing NP-Card for L-2-Amino-4-methoxy-trans-3-butenoic acid (NP0021420)

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Record Information

Version

1.0

Created at

2021-01-06 06:40:14 UTC

Updated at

2021-07-15 17:36:18 UTC

NP-MRD ID

NP0021420

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-2-Amino-4-methoxy-trans-3-butenoic acid

Provided By

NPAtlas

Description

L-2-Amino-4-methoxy-trans-3-butenoic acid is found in Pseudomonas. It was first documented in 1972 (PMID: 4624612). Based on a literature review very few articles have been published on (2S,3E)-2-amino-4-methoxybut-3-enoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105153D          

 18 17  0  0  0  0            999 V2000
    3.0949   -0.2812    0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0684   -0.3553    1.2354 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515    0.2737    0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   -0.2290    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2511    0.4967   -0.2363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8186    0.9458    1.0103 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2064   -0.3537   -0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302   -0.5809   -0.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743   -0.8963   -2.1995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    0.7752    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7351   -0.7110   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9780   -0.8548    0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289    1.2144    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -1.1671   -0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9905    1.3944   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525    0.1827    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6584    1.5226    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.3763   -2.2940 H   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5 15  1  6  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  9 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021420

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO3/c1-9-3-2-4(6)5(7)8/h2-4H,6H2,1H3,(H,7,8)/b3-2+/t4-/m0/s1

> <INCHI_KEY>
HLOPMQJRUIOMJO-ZPYNKGFJSA-N

> <FORMULA>
C5H9NO3

> <MOLECULAR_WEIGHT>
131.131

> <EXACT_MASS>
131.058243154

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.581946924962033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3E)-2-amino-4-methoxybut-3-enoic acid

> <ALOGPS_LOGP>
-2.54

> <JCHEM_LOGP>
-2.9434885073308825

> <ALOGPS_LOGS>
0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.190015727180587

> <JCHEM_PKA_STRONGEST_BASIC>
8.876919509167415

> <JCHEM_POLAR_SURFACE_AREA>
72.55

> <JCHEM_REFRACTIVITY>
31.640300000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3E)-2-amino-4-methoxybut-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.095  -0.281   0.267  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.068  -0.355   1.235  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.852   0.274   0.912  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.010  -0.229   0.048  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.251   0.497  -0.236  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.819   0.946   1.010  0.00  0.00           N+0
HETATM    7  C   UNK     0      -2.206  -0.354  -0.976  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.330  -0.581  -0.480  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.874  -0.896  -2.200  0.00  0.00           O+0
HETATM   10  H   UNK     0       3.349   0.775   0.071  0.00  0.00           H+0
HETATM   11  H   UNK     0       2.735  -0.711  -0.692  0.00  0.00           H+0
HETATM   12  H   UNK     0       3.978  -0.855   0.600  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.629   1.214   1.417  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.247  -1.167  -0.446  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.991   1.394  -0.850  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.853   0.183   1.693  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.658   1.523   0.919  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.981  -1.376  -2.294  0.00  0.00           H+0
CONECT    1    2   10   11   12                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6    7   15                                             
CONECT    6    5   16   17                                                  
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   18                                                       
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    3                                                            
CONECT   14    4                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    6                                                            
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S,3E)-2-Amino-4-methoxybut-3-enoate	Generator
2-Amino-4-methoxy-3-butenoic acid, (e)-isomer	MeSH
2-Amino-4-methoxy-3-butenoic acid	MeSH
L-2-Amino-4-methoxy-trans-3-butenoic acid	MeSH

Chemical Formula

C₅H₉NO₃

Average Mass

131.1310 Da

Monoisotopic Mass

131.05824 Da

IUPAC Name

(2S,3E)-2-amino-4-methoxybut-3-enoic acid

Traditional Name

(2S,3E)-2-amino-4-methoxybut-3-enoic acid

CAS Registry Number

Not Available

SMILES

CO\C=C\[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C5H9NO3/c1-9-3-2-4(6)5(7)8/h2-4H,6H2,1H3,(H,7,8)/b3-2+/t4-/m0/s1

InChI Key

HLOPMQJRUIOMJO-ZPYNKGFJSA-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
Pseudomonas	NPAtlas	4624612

Species Where Detected

Species Name	Source	Reference
Pseudomonas aeruginosa ATCC 7700	KNApSAcK Database	22123792

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	-2.5	ALOGPS
logP	-2.9	ChemAxon
logS	0.27	ALOGPS
pKa (Strongest Acidic)	2.19	ChemAxon
pKa (Strongest Basic)	8.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.64 m³·mol⁻¹	ChemAxon
Polarizability	12.58 Å³	ChemAxon
Number of Rings	0	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

NPAtlas ID

NPA017445

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4945225

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129320491

PDB ID

Not Available

ChEBI ID

156361

Good Scents ID

Not Available

References

General References

Scannel JP, Pruess DL, Demny TC, Sello LH, Williams T: Antimetabolites produced by microorganisms. V. L-2-amino-4-methoxy-trans-3-butenoic acid. J Antibiot (Tokyo). 1972 Feb;25(2):122-7. doi: 10.7164/antibiotics.25.122. [PubMed:4624612 ]

Showing NP-Card for L-2-Amino-4-methoxy-trans-3-butenoic acid (NP0021420)

MOL for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

3D MOL for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

3D SDF for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

3D-SDF for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

PDB for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

3D PDB for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

SMILES for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

INCHI for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

Structure for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)

3D Structure for NP0021420 (L-2-Amino-4-methoxy-trans-3-butenoic acid)