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Showing NP-Card for DIBOA hexose (NP0050025)

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Record Information
Version2.0
Created at2022-03-17 21:21:59 UTC
Updated at2022-03-17 21:22:00 UTC
NP-MRD IDNP0050025
Secondary Accession NumbersNone
Natural Product Identification
Common NameDIBOA hexose
DescriptionCHEBI:80091 Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. CHEBI:80091 Is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050025 (DIBOA hexose)


  Mrv1652309241920302D          

 30 32  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  6  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  1  0  0  0  0
  9 17  1  1  0  0  0
 10 18  1  1  0  0  0
 11 19  1  1  0  0  0
 20 12  2  0  0  0  0
 21 15  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
 23  8  1  0  0  0  0
 23 13  1  0  0  0  0
 13 24  1  6  0  0  0
 24 14  1  0  0  0  0
  8 25  1  1  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
 11 28  1  6  0  0  0
 13 29  1  1  0  0  0
 30 14  1  0  0  0  0
M  END
Download

3D MOL for NP0050025 (DIBOA hexose)

Download
3D SDF for NP0050025 (DIBOA hexose)

  Mrv1652309241920302D          

 30 32  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  6  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  1  0  0  0  0
  9 17  1  1  0  0  0
 10 18  1  1  0  0  0
 11 19  1  1  0  0  0
 20 12  2  0  0  0  0
 21 15  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
 23  8  1  0  0  0  0
 23 13  1  0  0  0  0
 13 24  1  6  0  0  0
 24 14  1  0  0  0  0
  8 25  1  1  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
 11 28  1  6  0  0  0
 13 29  1  1  0  0  0
 30 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)OC2=CC=CC=C2N(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO9/c16-5-8-9(17)10(18)11(19)13(23-8)24-14-12(20)15(21)6-3-1-2-4-7(6)22-14/h1-4,8-11,13-14,16-19,21H,5H2/t8-,9-,10+,11-,13+,14?/m1/s1

> <INCHI_KEY>
OUSLYTBGQGKTME-BJPDSMLBSA-N

> <FORMULA>
C14H17NO9

> <MOLECULAR_WEIGHT>
343.288

> <EXACT_MASS>
343.090331131

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.190530377861677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1,4-benzoxazin-3-one

> <ALOGPS_LOGP>
-1.23

> <JCHEM_LOGP>
-1.6677531166666661

> <ALOGPS_LOGS>
-1.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.207167633849146

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.897427291522069

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849224353024

> <JCHEM_POLAR_SURFACE_AREA>
149.15

> <JCHEM_REFRACTIVITY>
74.4206

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diboa-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050025 (DIBOA hexose)
Download
PDB for NP0050025 (DIBOA hexose)
HEADER    PROTEIN                                 24-SEP-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-19         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.667  -0.000   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       9.336   0.770   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      10.669  -1.540   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       9.336  -3.850   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.668  -3.850   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8   16                                                       
CONECT    6    3    7   15                                                  
CONECT    7    4    6   22                                                  
CONECT    8    5    9   23   25                                             
CONECT    9    8   10   17   26                                             
CONECT   10    9   11   18   27                                             
CONECT   11   10   13   19   28                                             
CONECT   12   14   15   20                                                  
CONECT   13   11   23   24   29                                             
CONECT   14   12   22   24   30                                             
CONECT   15    6   12   21                                                  
CONECT   16    5                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   15                                                            
CONECT   22    7   14                                                       
CONECT   23    8   13                                                       
CONECT   24   13   14                                                       
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Download
3D PDB for NP0050025 (DIBOA hexose)
Download
SMILES for NP0050025 (DIBOA hexose)
[H]C1(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)OC2=CC=CC=C2N(O)C1=O
Download
INCHI for NP0050025 (DIBOA hexose)
InChI=1S/C14H17NO9/c16-5-8-9(17)10(18)11(19)13(23-8)24-14-12(20)15(21)6-3-1-2-4-7(6)22-14/h1-4,8-11,13-14,16-19,21H,5H2/t8-,9-,10+,11-,13+,14?/m1/s1
Download
View in JSmol
Synonyms
ValueSource
2,4-Dihydroxy-1,4-benzoxazin-3-one glucosideKegg
(2R)-4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranosideKegg
(2R)-4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl b-D-glucopyranosideGenerator
(2R)-4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl β-D-glucopyranosideGenerator
Chemical FormulaC14H17NO9
Average Mass343.2880 Da
Monoisotopic Mass343.09033 Da
IUPAC Name4-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1,4-benzoxazin-3-one
Traditional Namediboa-glucoside
CAS Registry NumberNot Available
SMILES
[H]C1(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)OC2=CC=CC=C2N(O)C1=O
InChI Identifier
InChI=1S/C14H17NO9/c16-5-8-9(17)10(18)11(19)13(23-8)24-14-12(20)15(21)6-3-1-2-4-7(6)22-14/h1-4,8-11,13-14,16-19,21H,5H2/t8-,9-,10+,11-,13+,14?/m1/s1
InChI KeyOUSLYTBGQGKTME-BJPDSMLBSA-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 o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentO-glycosyl compounds  
Alternative Parents
Substituents
  • Hexose monosaccharide
    • 

  • Benzoxazinone
    • 

  • O-glycosyl compound
    • 

  • Benzomorpholine
    • 

  • Benzoxazine
    • 

  • Monosaccharide
    • 

  • Benzenoid
    • 

  • Oxane
    • 

  • Oxazinane
    • 

  • Hydroxamic acid
    • 

  • Secondary alcohol
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organonitrogen compound
    • 

  • Primary alcohol
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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-1.2ALOGPS
logP-1.7ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.15 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.42 m³·mol⁻¹ChemAxon
Polarizability31.19 ųChemAxon
Number of Rings3ChemAxon
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 ID4475737  
KEGG Compound IDC15772  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5316752  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available