NP-MRD: Showing NP-Card for (S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside (NP0335910)

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Record Information

Version

2.0

Created at

2024-09-11 03:49:25 UTC

Updated at

2024-09-11 03:49:25 UTC

NP-MRD ID

NP0335910

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside

Description

(S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Based on a literature review very few articles have been published on (S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262306212D          

 23 24  0  0  0  0            999 V2000
    0.7145    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257   -0.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613    0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    0.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173    0.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324    1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.2911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -1.3131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -0.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378    1.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7679    2.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376    3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763    0.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  2  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  2  0  0  0  0
 20 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22  6  1  0  0  0  0
 22 10  1  0  0  0  0
 23 12  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335910

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CN(OC1=O)C1OC(CO)C(O)C(O)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C12H18N2O9/c13-5(11(19)20)1-4-2-14(23-12(4)21)10-9(18)8(17)7(16)6(3-15)22-10/h2,5-10,15-18H,1,3,13H2,(H,19,20)

> <INCHI_KEY>
OURYTICKCZBKFC-UHFFFAOYNA-N

> <FORMULA>
C12H18N2O9

> <MOLECULAR_WEIGHT>
334.281

> <EXACT_MASS>
334.101230168

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.00508019743981

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-{5-oxo-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,5-dihydro-1,2-oxazol-4-yl}propanoic acid

> <JCHEM_LOGP>
-5.825670016192569

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.408998559022654

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.51002547897317

> <JCHEM_PKA_STRONGEST_BASIC>
9.455476494711808

> <JCHEM_POLAR_SURFACE_AREA>
183.00999999999996

> <JCHEM_REFRACTIVITY>
70.0099

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-{5-oxo-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,2-oxazol-4-yl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       1.334   8.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.580   5.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.661  -1.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   8.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.288   0.202   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.819   0.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.446   1.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.540   3.015   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.009   2.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  10.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.088   5.565   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.334   8.010   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       2.104   4.100   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       3.566  -2.451   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.725  -0.883   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.977   1.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.167   4.422   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  11.090   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  11.090   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.377   6.041   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.382   1.447   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.564   4.100   0.000  0.00  0.00           O+0
CONECT    1    4    5                                                       
CONECT    2    4   14                                                       
CONECT    3    6   15                                                       
CONECT    4    1    2   12                                                  
CONECT    5    1   11   13                                                  
CONECT    6    3    7   22                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   14   22                                                  
CONECT   11    5   19   20                                                  
CONECT   12    4   21   23                                                  
CONECT   13    5                                                            
CONECT   14    2   10   23                                                  
CONECT   15    3                                                            
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   11                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22    6   10                                                       
CONECT   23   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoate N2-glucoside	Generator

Chemical Formula

C₁₂H₁₈N₂O₉

Average Mass

334.2810 Da

Monoisotopic Mass

334.10123 Da

IUPAC Name

2-amino-3-{5-oxo-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,5-dihydro-1,2-oxazol-4-yl}propanoic acid

Traditional Name

2-amino-3-{5-oxo-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,2-oxazol-4-yl}propanoic acid

CAS Registry Number

Not Available

SMILES

NC(CC1=CN(OC1=O)C1OC(CO)C(O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1/C12H18N2O9/c13-5(11(19)20)1-4-2-14(23-12(4)21)10-9(18)8(17)7(16)6(3-15)22-10/h2,5-10,15-18H,1,3,13H2,(H,19,20)

InChI Key

OURYTICKCZBKFC-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

Hexose monosaccharide
N-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
Aralkylamine
Monosaccharide
Oxane
Azole
Heteroaromatic compound
Isoxazole
Vinylogous amide
Amino acid or derivatives
Amino acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Amine
Organopnictogen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Organic oxide
Primary aliphatic amine
Primary amine
Organonitrogen compound
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-5.8	ChemAxon
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	9.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.01 m³·mol⁻¹	ChemAxon
Polarizability	31.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

Not Available

Showing NP-Card for (S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside (NP0335910)

MOL for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

3D MOL for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

3D SDF for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

3D-SDF for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

PDB for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

3D PDB for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

SMILES for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

INCHI for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

Structure for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)

3D Structure for NP0335910 ((S)-a-Amino-2,5-dihydro-5-oxo-4-isoxazolepropanoic acid N2-glucoside)