NP-MRD: Showing NP-Card for methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate (NP0300907)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 13:34:29 UTC

Updated at

2022-09-10 13:34:30 UTC

NP-MRD ID

NP0300907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate

Description

Euscamine B belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate is found in Euscaphis japonica. Based on a literature review very few articles have been published on Euscamine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.5205    2.1209    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2554    0.8335    0.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945    0.5861   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4135    1.5810   -1.5805 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4448   -0.8104   -1.3116 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8647   -1.7230   -0.2925 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719   -0.9998   -1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670   -0.6991   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -0.8412   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765   -1.1879   -1.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553   -0.6100    0.3279 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7909   -0.2077    1.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494   -0.7746    0.0279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1496   -1.8062    0.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5319   -1.6135    0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6357   -0.1250    0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4868    0.3670    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2039    1.8309    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2750    2.5834    0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1956    2.9317    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6441    2.2043    0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    2.2913    1.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -0.9668   -2.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759   -1.2272    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8328   -2.0684   -0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796   -0.2999   -2.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -2.0571   -1.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -1.3179    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.3651   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141    0.7919    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141   -0.2474    2.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166   -0.9089    2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8284   -1.0837   -1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0518   -2.0333    1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8806   -1.9982   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5001    0.4174    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0082    2.1701   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.0292    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0773    2.5034    0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  6
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  6
 15 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv1652309102215342D          

 19 19  0  0  0  0            999 V2000
   -0.5662   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483   -5.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628   -3.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -6.0577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206   -3.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -5.2327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1496   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2358   -3.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428   -3.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4553   -4.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9033   -5.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748   -5.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8594   -6.2177    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300907

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(N)CCC(=O)N(C)C1OCC=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C12H20N2O5/c1-14(11-8(7-15)5-6-19-11)10(16)4-3-9(13)12(17)18-2/h5,9,11,15H,3-4,6-7,13H2,1-2H3

> <INCHI_KEY>
CDAYVDYQRNYMKN-UHFFFAOYSA-N

> <FORMULA>
C12H20N2O5

> <MOLECULAR_WEIGHT>
272.301

> <EXACT_MASS>
272.137221752

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.730652695794653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate

> <JCHEM_LOGP>
-1.5483750389999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.037683440550769

> <JCHEM_PKA_STRONGEST_BASIC>
7.183911478021317

> <JCHEM_POLAR_SURFACE_AREA>
102.09

> <JCHEM_REFRACTIVITY>
67.8598

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.057  -8.998   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.277  -9.768   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.610  -8.998   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.610  -7.458   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.944  -9.768   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.944 -11.308   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.278  -8.998   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.612  -9.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.945  -8.998   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.945  -7.458   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       8.279  -9.768   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       8.279 -11.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.613  -8.998   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.774  -7.466   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.280  -7.146   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.050  -8.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.019  -9.624   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.340 -11.130   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.804 -11.606   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₂₀N₂O₅

Average Mass

272.3010 Da

Monoisotopic Mass

272.13722 Da

IUPAC Name

methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate

Traditional Name

methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(N)CCC(=O)N(C)C1OCC=C1CO

InChI Identifier

InChI=1S/C12H20N2O5/c1-14(11-8(7-15)5-6-19-11)10(16)4-3-9(13)12(17)18-2/h5,9,11,15H,3-4,6-7,13H2,1-2H3

InChI Key

CDAYVDYQRNYMKN-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

Species Name	Source	Reference
Euscaphis japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Alpha-amino acid ester
Fatty acid ester
N-acyl-amine
Fatty acyl
Dihydrofuran
Tertiary carboxylic acid amide
Methyl ester
Carboxamide group
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Amine
Organic nitrogen compound
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	-1.5	ChemAxon
pKa (Strongest Acidic)	15.04	ChemAxon
pKa (Strongest Basic)	7.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.09 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.86 m³·mol⁻¹	ChemAxon
Polarizability	27.73 Å³	ChemAxon
Number of Rings	1	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8763615

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10588240

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate (NP0300907)

MOL for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

3D MOL for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

3D SDF for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

3D-SDF for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

PDB for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

3D PDB for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

SMILES for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

INCHI for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

Structure for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)

3D Structure for NP0300907 (methyl 2-amino-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl](methyl)carbamoyl}butanoate)