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Showing NP-Card for (2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one (NP0321370)

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Record Information
Version2.0
Created at2022-09-11 23:32:45 UTC
Updated at2022-09-11 23:32:45 UTC
NP-MRD IDNP0321370
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one
Description(2S,3R)-4-hydroxy-6-methyl-2-[(2R)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]Octa-4,6-dien-8-one belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Based on a literature review very few articles have been published on (2S,3R)-4-hydroxy-6-methyl-2-[(2R)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]Octa-4,6-dien-8-one.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)


  Mrv1652309122201322D          

 17 18  0  0  1  0            999 V2000
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    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  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
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3D MOL for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)

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3D SDF for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)

  Mrv1652309122201322D          

 17 18  0  0  1  0            999 V2000
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    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  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)[C@H]1O[C@]11C(=O)C=C(C)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO4/c1-4-6(2)9(15)10-12(17-10)8(14)5-7(3)13-11(12)16/h5-6,10H,4H2,1-3H3,(H,13,16)/t6-,10-,12-/m1/s1

> <INCHI_KEY>
GAWXSBCGUQFYOO-KXHDPYLZSA-N

> <FORMULA>
C12H15NO4

> <MOLECULAR_WEIGHT>
237.255

> <EXACT_MASS>
237.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.340791554321463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-4-hydroxy-6-methyl-2-[(2R)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one

> <JCHEM_LOGP>
-0.6435255212585981

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.157532170093685

> <JCHEM_PKA_STRONGEST_ACIDIC>
-8.677838343474242

> <JCHEM_PKA_STRONGEST_BASIC>
10.645600244942322

> <JCHEM_POLAR_SURFACE_AREA>
79.26

> <JCHEM_REFRACTIVITY>
61.23120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-4-hydroxy-6-methyl-2-[(2R)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)
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PDB for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)
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      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.437   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.644  -0.564   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -1.897   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    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   16                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

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3D PDB for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)
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SMILES for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)
CC[C@@H](C)C(=O)[C@H]1O[C@]11C(=O)C=C(C)N=C1O
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INCHI for NP0321370 ((2s,3r)-4-hydroxy-6-methyl-2-[(2r)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one)
InChI=1S/C12H15NO4/c1-4-6(2)9(15)10-12(17-10)8(14)5-7(3)13-11(12)16/h5-6,10H,4H2,1-3H3,(H,13,16)/t6-,10-,12-/m1/s1
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SynonymsNot Available
Chemical FormulaC12H15NO4
Average Mass237.2550 Da
Monoisotopic Mass237.10011 Da
IUPAC Name(2S,3R)-4-hydroxy-6-methyl-2-[(2R)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one
Traditional Name(2S,3R)-4-hydroxy-6-methyl-2-[(2R)-2-methylbutanoyl]-1-oxa-5-azaspiro[2.5]octa-4,6-dien-8-one
CAS Registry NumberNot Available
SMILES
CC[C@@H](C)C(=O)[C@H]1O[C@]11C(=O)C=C(C)N=C1O
InChI Identifier
InChI=1S/C12H15NO4/c1-4-6(2)9(15)10-12(17-10)8(14)5-7(3)13-11(12)16/h5-6,10H,4H2,1-3H3,(H,13,16)/t6-,10-,12-/m1/s1
InChI KeyGAWXSBCGUQFYOO-KXHDPYLZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentMonosaccharides  
Alternative Parents
Substituents
  • Monosaccharide
    • 

  • Cyclic carboximidic acid
    • 

  • Ketone
    • 

  • Dialkyl ether
    • 

  • Oxirane
    • 

  • Ether
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.64ChemAxon
pKa (Strongest Acidic)-8.7ChemAxon
pKa (Strongest Basic)10.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area79.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.23 m³·mol⁻¹ChemAxon
Polarizability23.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162849919  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]