NP-MRD: Showing NP-Card for (R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside (NP0048715)

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Record Information

Version

2.0

Created at

2022-03-17 21:01:03 UTC

Updated at

2022-03-17 21:01:03 UTC

NP-MRD ID

NP0048715

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside

Description

DHBOA-Glc 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. DHBOA-Glc is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, DHBOA-Glc has been detected, but not quantified in, a few different foods, such as alcoholic beverages, coffee and coffee products, and tea. (R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside is found in Coix lachryma-jobi. This could make dhboa-GLC a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210202D          

 24 26  0  0  0  0            999 V2000
   -0.9394    0.7539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6361    0.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4044    0.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1026    0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096   -0.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6128   -0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -0.8967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4830    0.8101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137    0.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876   -0.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5340   -0.8390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6472    0.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014    0.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9818    1.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7761   -0.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -1.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656   -0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147    0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7074    0.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -0.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC3=CC(O)=CC=C3NC2=O)C(O)C(O)C1O

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

> <INCHI_KEY>
VUFDXOACUHDTLI-UHFFFAOYSA-N

> <FORMULA>
C14H17NO9

> <MOLECULAR_WEIGHT>
343.2861

> <EXACT_MASS>
343.090331147

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
32.003941715643165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.06

> <JCHEM_LOGP>
-1.6085267140000004

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.451443759560323

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.380269307938281

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849224104405

> <JCHEM_POLAR_SURFACE_AREA>
157.94

> <JCHEM_REFRACTIVITY>
76.4177

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.31e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.754   1.407   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.054   0.586   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.488   1.351   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.792   0.527   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.745  -1.012   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.311  -1.777   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.011  -0.953   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.653  -1.674   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.902   1.512   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.399   0.687   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.350  -0.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.997  -1.566   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.095  -1.204   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.075   0.343   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.296   1.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.268   2.598   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.566   3.447   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.049  -1.835   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.453  -3.447   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.424  -1.907   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.722  -1.063   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.627   0.350   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.920   1.192   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.049  -1.771   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7   11                                                       
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11    8   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    5                                                            
CONECT   19   20                                                            
CONECT   20   13   19   21                                                  
CONECT   21   20   22   24                                                  
CONECT   22   15   21   23                                                  
CONECT   23   22                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₇NO₉

Average Mass

343.2861 Da

Monoisotopic Mass

343.09033 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

28512-70-1

SMILES

OCC1OC(OC2OC3=CC(O)=CC=C3NC2=O)C(O)C(O)C1O

InChI Identifier

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

InChI Key

VUFDXOACUHDTLI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coix lacryma-jobi	Plant	KNApSAcK

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
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Benzenoid
Oxazinane
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Acetal
Polyol
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Primary alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-1.1	ALOGPS
logP	-1.6	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	9.38	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	157.94 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	76.42 m³·mol⁻¹	ChemAxon
Polarizability	32 Å³	ChemAxon
Number of Rings	3	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

HMDB0037261

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016278

KNApSAcK ID

Not Available

Chemspider ID

515112

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

592555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside (NP0048715)

MOL for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

3D MOL for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

3D SDF for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

3D-SDF for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

PDB for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

3D PDB for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

SMILES for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

INCHI for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

Structure for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)

3D Structure for NP0048715 ((R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside)