NP-MRD: Showing NP-Card for Glucopyranosyl anthranilate (NP0049869)

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Record Information

Version

2.0

Created at

2022-03-17 21:19:25 UTC

Updated at

2022-03-17 21:19:25 UTC

NP-MRD ID

NP0049869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucopyranosyl anthranilate

Description

Beta-D-Glucopyranosyl anthranilate belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Beta-D-Glucopyranosyl anthranilate is a moderately basic compound (based on its pKa). Outside of the human body, beta-D-Glucopyranosyl anthranilate has been detected, but not quantified in, corns and fruits. Glucopyranosyl anthranilate is found in Bromelia plumieri. This could make beta-D-glucopyranosyl anthranilate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312432D          

 21 22  0  0  0  0            999 V2000
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    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
 12  6  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  5  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 20  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=CC=C1C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H17NO7/c14-7-4-2-1-3-6(7)12(19)21-13-11(18)10(17)9(16)8(5-15)20-13/h1-4,8-11,13,15-18H,5,14H2

> <INCHI_KEY>
GTQKOJVFDJDUGN-UHFFFAOYSA-N

> <FORMULA>
C13H17NO7

> <MOLECULAR_WEIGHT>
299.2766

> <EXACT_MASS>
299.100501903

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.10060678648179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-aminobenzoate

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-0.6161653233333328

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19443432484945

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195710678568044

> <JCHEM_PKA_STRONGEST_BASIC>
2.001633592894218

> <JCHEM_POLAR_SURFACE_AREA>
142.47

> <JCHEM_REFRACTIVITY>
70.4458

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-aminobenzoate

> <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       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   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      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.667  10.780   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -4.001  16.170   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.335  13.860   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  13.090   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  10.780   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   15                                                       
CONECT    6    3    7   12                                                  
CONECT    7    4    6   14                                                  
CONECT    8    5    9   20                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   13   18                                                  
CONECT   12    6   19   21                                                  
CONECT   13   11   20   21                                                  
CONECT   14    7                                                            
CONECT   15    5                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20    8   13                                                       
CONECT   21   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
b-D-Glucopyranosyl anthranilate	Generator
b-D-Glucopyranosyl anthranilic acid	Generator
beta-D-Glucopyranosyl anthranilic acid	Generator
Β-D-glucopyranosyl anthranilate	Generator
Β-D-glucopyranosyl anthranilic acid	Generator
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-aminobenzoic acid	Generator
Glucopyranosyl anthranilic acid	Generator

Chemical Formula

C₁₃H₁₇NO₇

Average Mass

299.2766 Da

Monoisotopic Mass

299.10050 Da

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-aminobenzoate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-aminobenzoate

CAS Registry Number

13283-31-3

SMILES

NC1=CC=CC=C1C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C13H17NO7/c14-7-4-2-1-3-6(7)12(19)21-13-11(18)10(17)9(16)8(5-15)20-13/h1-4,8-11,13,15-18H,5,14H2

InChI Key

GTQKOJVFDJDUGN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bromelia plumieri	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 hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Aminobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Monocyclic benzene moiety
Oxane
Benzenoid
Vinylogous amide
Secondary alcohol
Amino acid or derivatives
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Acetal
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Amine
Primary alcohol
Organic nitrogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-12835 )

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	-1.6	ALOGPS
logP	-0.62	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	142.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.45 m³·mol⁻¹	ChemAxon
Polarizability	29.1 Å³	ChemAxon
Number of Rings	2	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

HMDB0041517

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021492

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

75595895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glucopyranosyl anthranilate (NP0049869)

MOL for NP0049869 (Glucopyranosyl anthranilate)

3D MOL for NP0049869 (Glucopyranosyl anthranilate)

3D SDF for NP0049869 (Glucopyranosyl anthranilate)

3D-SDF for NP0049869 (Glucopyranosyl anthranilate)

PDB for NP0049869 (Glucopyranosyl anthranilate)

3D PDB for NP0049869 (Glucopyranosyl anthranilate)

SMILES for NP0049869 (Glucopyranosyl anthranilate)

INCHI for NP0049869 (Glucopyranosyl anthranilate)

Structure for NP0049869 (Glucopyranosyl anthranilate)

3D Structure for NP0049869 (Glucopyranosyl anthranilate)