NP-MRD: Showing NP-Card for 2-(Arabinosylamino)-3-(glucosylamino)propanenitrile (NP0335318)

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Record Information

Version

2.0

Created at

2024-09-11 01:03:35 UTC

Updated at

2024-09-11 01:03:36 UTC

NP-MRD ID

NP0335318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(Arabinosylamino)-3-(glucosylamino)propanenitrile

Description

2-(Arabinosylamino)-3-(glucosylamino)propanenitrile belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Based on a literature review very few articles have been published on 2-(Arabinosylamino)-3-(glucosylamino)propanenitrile.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262303352D          

 26 27  0  0  0  0            999 V2000
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  3  0  0  0  0
 16  2  1  0  0  0  0
 16 13  1  0  0  0  0
 17  5  1  0  0  0  0
 17 14  1  0  0  0  0
 18  3  1  0  0  0  0
 19  6  1  0  0  0  0
 20  8  1  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25  4  1  0  0  0  0
 25 14  1  0  0  0  0
 26  7  1  0  0  0  0
 26 13  1  0  0  0  0
M  END


  Mrv2104 05262303352D          

 26 27  0  0  0  0            999 V2000
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  3  0  0  0  0
 16  2  1  0  0  0  0
 16 13  1  0  0  0  0
 17  5  1  0  0  0  0
 17 14  1  0  0  0  0
 18  3  1  0  0  0  0
 19  6  1  0  0  0  0
 20  8  1  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25  4  1  0  0  0  0
 25 14  1  0  0  0  0
 26  7  1  0  0  0  0
 26 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(NCC(NC2OCC(O)C(O)C2O)C#N)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C14H25N3O9/c15-1-5(17-14-11(23)8(20)6(19)4-25-14)2-16-13-12(24)10(22)9(21)7(3-18)26-13/h5-14,16-24H,2-4H2

> <INCHI_KEY>
BTGYSUHNSKOEKC-UHFFFAOYNA-N

> <FORMULA>
C14H25N3O9

> <MOLECULAR_WEIGHT>
379.366

> <EXACT_MASS>
379.159079397

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.00304002827713

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}-2-[(3,4,5-trihydroxyoxan-2-yl)amino]propanenitrile

> <JCHEM_LOGP>
-5.006982780666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.695941216095045

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.182841812694877

> <JCHEM_PKA_STRONGEST_BASIC>
4.540626788168605

> <JCHEM_POLAR_SURFACE_AREA>
207.91999999999996

> <JCHEM_REFRACTIVITY>
81.5887

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}-2-[(3,4,5-trihydroxyoxan-2-yl)amino]propanenitrile

> <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       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   9.240   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -1.334   5.390   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.668   8.470   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.668   5.390   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    5   15                                                       
CONECT    2    5   16                                                       
CONECT    3    7   18                                                       
CONECT    4    6   25                                                       
CONECT    5    1    2   17                                                  
CONECT    6    4    8   19                                                  
CONECT    7    3    9   26                                                  
CONECT    8    6   11   20                                                  
CONECT    9    7   10   21                                                  
CONECT   10    9   12   22                                                  
CONECT   11    8   14   23                                                  
CONECT   12   10   13   24                                                  
CONECT   13   12   16   26                                                  
CONECT   14   11   17   25                                                  
CONECT   15    1                                                            
CONECT   16    2   13                                                       
CONECT   17    5   14                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25    4   14                                                       
CONECT   26    7   13                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₅N₃O₉

Average Mass

379.3660 Da

Monoisotopic Mass

379.15908 Da

IUPAC Name

3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}-2-[(3,4,5-trihydroxyoxan-2-yl)amino]propanenitrile

Traditional Name

3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}-2-[(3,4,5-trihydroxyoxan-2-yl)amino]propanenitrile

CAS Registry Number

Not Available

SMILES

OCC1OC(NCC(NC2OCC(O)C(O)C2O)C#N)C(O)C(O)C1O

InChI Identifier

InChI=1/C14H25N3O9/c15-1-5(17-14-11(23)8(20)6(19)4-25-14)2-16-13-12(24)10(22)9(21)7(3-18)26-13/h5-14,16-24H,2-4H2

InChI Key

BTGYSUHNSKOEKC-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 cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
N-glycosyl compound
Monosaccharide
Oxane
Hemiaminal
Secondary alcohol
Secondary aliphatic amine
Oxacycle
Carbonitrile
Nitrile
Organoheterocyclic compound
Polyol
Secondary amine
Amine
Organic nitrogen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Primary alcohol
Hydrocarbon derivative
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	ChemAxon
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	4.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	207.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	81.59 m³·mol⁻¹	ChemAxon
Polarizability	36 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

Not Available

Showing NP-Card for 2-(Arabinosylamino)-3-(glucosylamino)propanenitrile (NP0335318)

MOL for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

3D MOL for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

3D SDF for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

3D-SDF for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

PDB for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

3D PDB for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

SMILES for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

INCHI for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

Structure for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)

3D Structure for NP0335318 (2-(Arabinosylamino)-3-(glucosylamino)propanenitrile)