NP-MRD: Showing NP-Card for DIBOA-Glc (NP0047718)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:48 UTC

Updated at

2022-03-17 20:44:49 UTC

NP-MRD ID

NP0047718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

DIBOA-Glc

Description

DIBOA-Glc, also known as diboa-glucoside or GDIMBOA, 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. DIBOA-Glc is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, DIBOA-Glc has been detected, but not quantified in, several different foods, such as cereals and cereal products, common wheats, corns, fats and oils, and ryes. DIBOA-Glc is found in Acanthus ebracteatus, Acanthus mollis , Acanthus montanus, Secale cereale and Zea mays. This could make diboa-GLC a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307192D          

 24 26  0  0  0  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  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  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  0  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
  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  0  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
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  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
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O

> <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

> <INCHI_KEY>
OUSLYTBGQGKTME-UHFFFAOYSA-N

> <FORMULA>
C14H17NO9

> <MOLECULAR_WEIGHT>
343.2861

> <EXACT_MASS>
343.090331147

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
31.53879809654804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-2-{[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>
7.8974272915220425

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         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
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                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   13   19                                                  
CONECT   12   14   15   20                                                  
CONECT   13   11   23   24                                                  
CONECT   14   12   22   24                                                  
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                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
2-(2,4-Dihydroxy-1,4-benzoxazin-3-one)-beta-D-glucopyranose	HMDB
Diboa-glucoside	HMDB
GDIMBOA	HMDB
(2R)-2-O-beta-D-Glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one	HMDB
DIBOA-GLC	MeSH

Chemical Formula

C₁₄H₁₇NO₉

Average Mass

343.2861 Da

Monoisotopic Mass

343.09033 Da

IUPAC Name

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

Traditional Name

4-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-1,4-benzoxazin-3-one

CAS Registry Number

155835-54-4

SMILES

OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O

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

InChI Key

OUSLYTBGQGKTME-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthus ebracteatus	LOTUS Database	35616633
Acanthus mollis	Plant	KNApSAcK
Acanthus montanus	LOTUS Database	35616633
Secale cereale	Plant	KNApSAcK
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-13811 )

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	-1.2	ALOGPS
logP	-1.7	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.42 m³·mol⁻¹	ChemAxon
Polarizability	31.54 Å³	ChemAxon
Number of Rings	3	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

HMDB0033734

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011858

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

58114415

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for DIBOA-Glc (NP0047718)

MOL for NP0047718 (DIBOA-Glc)

3D MOL for NP0047718 (DIBOA-Glc)

3D SDF for NP0047718 (DIBOA-Glc)

3D-SDF for NP0047718 (DIBOA-Glc)

PDB for NP0047718 (DIBOA-Glc)

3D PDB for NP0047718 (DIBOA-Glc)

SMILES for NP0047718 (DIBOA-Glc)

INCHI for NP0047718 (DIBOA-Glc)

Structure for NP0047718 (DIBOA-Glc)

3D Structure for NP0047718 (DIBOA-Glc)