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Showing NP-Card for Xanthurenate-8-O-beta-D-glucoside (NP0339190)

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Record Information
Version2.0
Created at2024-09-11 20:17:52 UTC
Updated at2024-09-11 20:17:52 UTC
NP-MRD IDNP0339190
Secondary Accession NumbersNone
Natural Product Identification
Common NameXanthurenate-8-O-beta-D-glucoside
DescriptionXanthurenate-8-O-beta-D-glucoside, also known as xanthurenic acid-8-O-b-D-glucoside or XAN8GLC, belongs to the class of organic compounds known as 1-(1z-alkenyl)-glycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one 1Z-alkenyl chain attached at the O1 position of a glycerol moiety through an ether linkage. The results from the analysis for its occurrence in double mutants, together with the fact that xanthurenic acid 8-glucoside share the same precursor as xanthurenic acid and xanthommatin, suggest that xanthurenic acid 8-glucoside formation is closely related to the regulation of the last step in the biosynthesis of xanthommatin. Xanthurenate-8-O-beta-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthurenic acid 8-O-beta-D-glucoside, a fluorescent metabolite, has been isolated from heads of eye-color mutants of Drosophila melanogaster (d) the specific activity is two times higher in heads than in bodies; and. This is the first time that a UDP-glucosyltransferase activity that utilizes xanthurenic acid has been demonstrated. Feeding experiments suggest that this glucoside is synthesized from 3-hydroxykynurenine and that free xanthurenic acid is not a precursor. Xanthurenate-8-O-beta-D-glucoside was first documented in 1985 (PMID: 3922986). Evidence is presented to show that the synthesis takes place via xanthurenic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)


  Mrv1652303102016502D          

 26 28  0  0  1  0            999 V2000
   12.4981  -16.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7836  -16.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7836  -17.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4981  -17.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4981  -18.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2126  -18.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9271  -18.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9271  -17.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -17.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -17.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -18.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0705  -18.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7849  -18.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0705  -19.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -20.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -19.8027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -18.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -21.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -21.4527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0705  -21.4527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7836  -18.9777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7836  -19.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0691  -18.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3546  -18.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0691  -17.7401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3546  -17.3276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3 25  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
Download

3D MOL for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)

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3D SDF for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)

  Mrv1652303102016502D          

 26 28  0  0  1  0            999 V2000
   12.4981  -16.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7836  -16.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7836  -17.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4981  -17.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4981  -18.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2126  -18.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9271  -18.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9271  -17.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -17.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -17.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -18.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0705  -18.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7849  -18.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0705  -19.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -20.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -19.8027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -18.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3560  -21.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6415  -21.4527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0705  -21.4527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7836  -18.9777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7836  -19.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0691  -18.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3546  -18.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0691  -17.7401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3546  -17.3276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3 25  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0339190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C3N=C(C=C(O)C3=CC=C2)C(O)=O)[C@@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO9/c18-5-10-12(20)13(21)14(22)16(26-10)25-9-3-1-2-6-8(19)4-7(15(23)24)17-11(6)9/h1-4,10,12-14,16,18,20-22H,5H2,(H,17,19)(H,23,24)/t10-,12+,13+,14+,16-/m1/s1

> <INCHI_KEY>
MYFHOUJDPFBJLH-XGJKELJWSA-N

> <FORMULA>
C16H17NO9

> <MOLECULAR_WEIGHT>
367.3075

> <EXACT_MASS>
367.090331147

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.99836803464858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-0.7008650316666662

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.393430559830419

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8727837250754455

> <JCHEM_PKA_STRONGEST_BASIC>
4.087455684224436

> <JCHEM_POLAR_SURFACE_AREA>
169.79999999999998

> <JCHEM_REFRACTIVITY>
82.9697

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)
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PDB for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0      23.330 -30.035   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      21.996 -30.805   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.996 -32.345   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      23.330 -33.115   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      23.330 -34.655   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      24.664 -35.425   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      25.997 -34.655   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.997 -33.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.331 -32.345   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.665 -33.115   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.665 -34.655   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.998 -35.425   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      31.332 -34.655   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      29.998 -36.965   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.665 -37.735   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      27.331 -36.965   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      27.331 -35.425   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.665 -39.275   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      27.331 -40.045   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      29.998 -40.045   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      21.996 -35.425   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.996 -36.965   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      20.662 -34.655   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      19.329 -35.425   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      20.662 -33.115   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      19.329 -32.345   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17    7   11   16                                                  
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    5   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25    3   23   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

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3D PDB for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)
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SMILES for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)
OC[C@H]1O[C@@H](OC2=C3N=C(C=C(O)C3=CC=C2)C(O)=O)[C@@H](O)[C@@H](O)[C@H]1O
Download
INCHI for NP0339190 (Xanthurenate-8-O-beta-D-glucoside)
InChI=1S/C16H17NO9/c18-5-10-12(20)13(21)14(22)16(26-10)25-9-3-1-2-6-8(19)4-7(15(23)24)17-11(6)9/h1-4,10,12-14,16,18,20-22H,5H2,(H,17,19)(H,23,24)/t10-,12+,13+,14+,16-/m1/s1
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View in JSmol
Synonyms
ValueSource
Xanthurenate-8-O-b-D-glucosideGenerator
Xanthurenate-8-O-β-D-glucosideGenerator
Xanthurenic acid-8-O-b-D-glucosideGenerator
Xanthurenic acid-8-O-beta-D-glucosideGenerator
Xanthurenic acid-8-O-β-D-glucosideGenerator
4,8-Dihydroxy-8-O-beta-D-glucoside-quinaldic acid anionHMDB
4,8-Dihydroxy-8-O-beta-D-glucoside-quinoline-2-carboxylic acid anionHMDB
4,8-Dihydroxy-8-O-beta-delta-glucoside-quinaldic acid anionHMDB
4,8-Dihydroxy-8-O-beta-delta-glucoside-quinoline-2-carboxylic acid anionHMDB
4,8-Dihydroxyquinaldic acid 8-O-beta-D-glucosideHMDB
4,8-Dihydroxyquinaldic acid 8-O-beta-delta-glucosideHMDB
4,8-Dihydroxyquinoline-2-carboxylic acid 8-O-beta-D-glucosideHMDB
4,8-Dihydroxyquinoline-2-carboxylic acid 8-O-beta-delta-glucosideHMDB
Xan8GLCHMDB
Xanthurenic acid 8-O-beta-D-glucosideHMDB
Xanthurenic acid 8-O-beta-delta-glucosideHMDB
Xanthurenic acid 8-O-glucosideHMDB
Cardinalic acidHMDB
4-Hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylateGenerator
Chemical FormulaC16H17NO9
Average Mass367.3075 Da
Monoisotopic Mass367.09033 Da
IUPAC Name4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid
Traditional Name4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=C3N=C(C=C(O)C3=CC=C2)C(O)=O)[C@@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C16H17NO9/c18-5-10-12(20)13(21)14(22)16(26-10)25-9-3-1-2-6-8(19)4-7(15(23)24)17-11(6)9/h1-4,10,12-14,16,18,20-22H,5H2,(H,17,19)(H,23,24)/t10-,12+,13+,14+,16-/m1/s1
InChI KeyMYFHOUJDPFBJLH-XGJKELJWSA-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 1-(1z-alkenyl)-glycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one 1Z-alkenyl chain attached at the O1 position of a glycerol moiety through an ether linkage.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassGlycerophospholipids  
Sub ClassGlycerophosphocholines  
Direct Parent1-(1Z-alkenyl)-glycero-3-phosphocholines  
Alternative Parents
Substituents
  • 1-(1z-alkenyl)-glycero-3-phosphocholine
    • 

  • Phosphocholine
    • 

  • Glycerol vinyl ether
    • 

  • Dialkyl phosphate
    • 

  • Organic phosphoric acid derivative
    • 

  • Phosphoric acid ester
    • 

  • Alkyl phosphate
    • 

  • Quaternary ammonium salt
    • 

  • Tetraalkylammonium salt
    • 

  • Secondary alcohol
    • 

  • Alcohol
    • 

  • Organic salt
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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-0.41ALOGPS
logP-0.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.87ChemAxon
pKa (Strongest Basic)4.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area169.8 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.97 m³·mol⁻¹ChemAxon
Polarizability34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013118  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029293  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481609  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ferre J, Real MD, Mensua JL, Jacobson KB: Xanthurenic acid 8-O-beta-D-glucoside, a novel tryptophan metabolite in eye-color mutants of Drosophila melanogaster. J Biol Chem. 1985 Jun 25;260(12):7509-14. [PubMed:3922986  ]