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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:32 UTC

Update Date

2022-03-07 02:52:35 UTC

HMDB ID

HMDB0030544

Secondary Accession Numbers

HMDB30544

Metabolite Identification

Common Name

Gnaphaliin

Description

Gnaphaliin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gnaphaliin is considered to be a flavonoid. Based on a literature review very few articles have been published on Gnaphaliin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030544
     RDKit          3D
Gnaphaliin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.6912   -2.7197   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -2.3570    0.1194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020   -1.5551   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438   -0.2064    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0513    0.5423    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    1.9391    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.7561    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2456    2.2182    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    0.8712    1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256    0.0405    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    0.4950   -0.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458   -0.0477   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    0.7128   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4755    2.0834   -0.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    2.6075    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8344    0.1799   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9629    0.9723   -0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230   -1.2022   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901   -1.9726   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995   -3.3665   -0.8359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611   -1.4081   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244   -2.1680   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -3.4072   -0.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2788   -3.6148   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6726   -1.8132   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7221   -2.8460   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    2.4182   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981    3.8279    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1194    2.8152    1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2424    0.4175    1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -1.0005    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6660    2.4510    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511    2.1183    1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386    3.7042    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8589    1.9685   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676   -1.6696   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -3.7847   -1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22  3  1  0
 10  5  1  0
 21 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END


  Mrv0541 05061305202D          

 23 25  0  0  0  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21 15  1  0  0  0  0
 22  2  1  0  0  0  0
 22 17  1  0  0  0  0
 23 14  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030544

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-21-15-11(19)8-10(18)12-13(20)17(22-2)14(23-16(12)15)9-6-4-3-5-7-9/h3-8,18-19H,1-2H3

> <INCHI_KEY>
OWQLBLNRUZULFV-UHFFFAOYSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.2895

> <EXACT_MASS>
314.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.224162259812548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3,8-dimethoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.7185862309999997

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.63511983625834

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.971536695703728

> <JCHEM_PKA_STRONGEST_BASIC>
-4.620870838959829

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
84.1148

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gnaphaliin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030544
     RDKit          3D
Gnaphaliin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.6912   -2.7197   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -2.3570    0.1194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020   -1.5551   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438   -0.2064    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0513    0.5423    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    1.9391    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.7561    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2456    2.2182    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    0.8712    1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256    0.0405    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    0.4950   -0.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458   -0.0477   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    0.7128   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4755    2.0834   -0.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    2.6075    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8344    0.1799   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9629    0.9723   -0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230   -1.2022   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901   -1.9726   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995   -3.3665   -0.8359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611   -1.4081   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244   -2.1680   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -3.4072   -0.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2788   -3.6148   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6726   -1.8132   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7221   -2.8460   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    2.4182   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981    3.8279    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1194    2.8152    1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2424    0.4175    1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -1.0005    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6660    2.4510    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511    2.1183    1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386    3.7042    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8589    1.9685   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676   -1.6696   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -3.7847   -1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22  3  1  0
 10  5  1  0
 21 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END

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   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5    9                                                       
CONECT    8   10   11                                                       
CONECT    9    6    7   14                                                  
CONECT   10    8   12   18                                                  
CONECT   11    8   15   19                                                  
CONECT   12   10   13   16                                                  
CONECT   13   12   17   20                                                  
CONECT   14    9   17   23                                                  
CONECT   15   11   16   21                                                  
CONECT   16   12   15   23                                                  
CONECT   17   13   14   22                                                  
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21    1   15                                                       
CONECT   22    2   17                                                       
CONECT   23   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0030544
HETATM    1  C1  UNL     1      -2.691  -2.720  -1.047  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.910  -2.357   0.119  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.802  -1.555  -0.003  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.844  -0.206   0.130  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.051   0.542   0.425  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.000   1.939   0.286  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.072   2.756   0.577  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.246   2.218   1.021  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.324   0.871   1.165  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.226   0.041   0.867  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.304   0.495  -0.020  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.446  -0.048  -0.282  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.609   0.713  -0.430  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.476   2.083  -0.280  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.644   2.607   1.025  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.834   0.180  -0.706  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.963   0.972  -0.845  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.923  -1.202  -0.848  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.790  -1.973  -0.707  1.00  0.00           C  
HETATM   20  O5  UNL     1       2.800  -3.366  -0.836  1.00  0.00           O  
HETATM   21  C16 UNL     1       1.561  -1.408  -0.427  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.424  -2.168  -0.286  1.00  0.00           C  
HETATM   23  O6  UNL     1       0.475  -3.407  -0.408  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.279  -3.615  -1.530  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.673  -1.813  -1.691  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.722  -2.846  -0.701  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.088   2.418  -0.065  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.998   3.828   0.459  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.119   2.815   1.263  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.242   0.417   1.515  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.341  -1.000   1.027  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.666   2.451   1.559  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.451   2.118   1.582  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.839   3.704   0.935  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.859   1.968  -0.735  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.868  -1.670  -1.067  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.697  -3.785  -1.041  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   11
CONECT    5    6    6   10
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   31
CONECT   11   12
CONECT   12   13   13   21
CONECT   13   14   16
CONECT   14   15
CONECT   15   32   33   34
CONECT   16   17   18   18
CONECT   17   35
CONECT   18   19   36
CONECT   19   20   21   21
CONECT   20   37
CONECT   21   22
CONECT   22   23   23
END

HMDB0030544
     RDKit          3D
Gnaphaliin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.6912   -2.7197   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -2.3570    0.1194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020   -1.5551   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438   -0.2064    0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0513    0.5423    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    1.9391    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.7561    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2456    2.2182    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    0.8712    1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256    0.0405    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    0.4950   -0.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458   -0.0477   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    0.7128   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4755    2.0834   -0.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    2.6075    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8344    0.1799   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9629    0.9723   -0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230   -1.2022   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901   -1.9726   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995   -3.3665   -0.8359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611   -1.4081   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244   -2.1680   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -3.4072   -0.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2788   -3.6148   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6726   -1.8132   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7221   -2.8460   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    2.4182   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981    3.8279    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1194    2.8152    1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2424    0.4175    1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -1.0005    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6660    2.4510    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511    2.1183    1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386    3.7042    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8589    1.9685   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676   -1.6696   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -3.7847   -1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22  3  1  0
 10  5  1  0
 21 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-O-Methyl-8-methoxygalangin	HMDB
5,7-Dihydroxy-3,8-dimethoxy-2-phenyl-4H-1-benzopyran-4-one	HMDB
5,7-Dihydroxy-3,8-dimethoxyflavone	HMDB
Gnaphalin	HMDB

Chemical Formula

C₁₇H₁₄O₆

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

IUPAC Name

5,7-dihydroxy-3,8-dimethoxy-2-phenyl-4H-chromen-4-one

Traditional Name

gnaphaliin

CAS Registry Number

33803-42-8

SMILES

COC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H14O6/c1-21-15-11(19)8-10(18)12-13(20)17(22-2)14(23-16(12)15)9-6-4-3-5-7-9/h3-8,18-19H,1-2H3

InChI Key

OWQLBLNRUZULFV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
3-methoxychromone
Chromone
1-benzopyran
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12113093 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 - 175 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	83.41 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	3.24	ALOGPS
logP	2.72	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.97	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.11 m³·mol⁻¹	ChemAxon
Polarizability	31.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.427	31661259
DarkChem	[M-H]-	172.934	31661259
DeepCCS	[M+H]+	173.439	30932474
DeepCCS	[M-H]-	171.081	30932474
DeepCCS	[M-2H]-	205.16	30932474
DeepCCS	[M+Na]+	180.416	30932474
AllCCS	[M+H]+	171.2	32859911
AllCCS	[M+H-H2O]+	167.6	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	171.9	32859911
AllCCS	[M+HCOO]-	171.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gnaphaliin	COC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C1	4338.3	Standard polar	33892256
Gnaphaliin	COC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C1	2769.1	Standard non polar	33892256
Gnaphaliin	COC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C1	2712.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gnaphaliin,1TMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C)=CC(O)=C2C1=O	2814.6	Semi standard non polar	33892256
Gnaphaliin,1TMS,isomer #2	COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O)=CC(O[Si](C)(C)C)=C2C1=O	2856.0	Semi standard non polar	33892256
Gnaphaliin,2TMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O	2820.8	Semi standard non polar	33892256
Gnaphaliin,1TBDMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O	3054.3	Semi standard non polar	33892256
Gnaphaliin,1TBDMS,isomer #2	COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3078.2	Semi standard non polar	33892256
Gnaphaliin,2TBDMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3238.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gnaphaliin GC-MS (Non-derivatized) - 70eV, Positive	splash10-08g1-0591000000-afe81f1e4f9ef00ee990	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gnaphaliin GC-MS (2 TMS) - 70eV, Positive	splash10-006x-3336900000-f7eb0e85bd43b38151c4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gnaphaliin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gnaphaliin , negative-QTOF	splash10-0002-0091000000-124a5e93428beae667de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gnaphaliin , positive-QTOF	splash10-0uxr-0019000000-9467bf5d8376c7f9f21e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gnaphaliin 6V, Positive-QTOF	splash10-014i-0129000000-30c3f0d40dcb17d95544	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gnaphaliin 6V, Negative-QTOF	splash10-01ot-0195000000-b9072a2dbe6d9c7b6075	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 10V, Positive-QTOF	splash10-014i-0009000000-74366254c71683d86cac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 20V, Positive-QTOF	splash10-014i-0009000000-f7b7fce9470ede53b4a9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 40V, Positive-QTOF	splash10-014i-2790000000-36ea33c39896b3ce66d1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 10V, Negative-QTOF	splash10-03di-0009000000-fd590dfdd66fe2b5e08d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 20V, Negative-QTOF	splash10-03di-0049000000-c02bf06f3fad2e3ab6f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 40V, Negative-QTOF	splash10-001i-1980000000-7c23df6d93ae35e0c7f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 10V, Positive-QTOF	splash10-014i-0009000000-2ba875095a8aafa31ef7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 20V, Positive-QTOF	splash10-014i-0009000000-cbffccd382907c719c4a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 40V, Positive-QTOF	splash10-0159-1913000000-246263a900cde4f573b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 10V, Negative-QTOF	splash10-03di-0009000000-f92a1b64ae90a24db158	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 20V, Negative-QTOF	splash10-03di-0309000000-ca1a12c3d6e59212f3b5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gnaphaliin 40V, Negative-QTOF	splash10-02w9-4911000000-5bf43f16327e1bd1b2a4	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002418

KNApSAcK ID

C00004556

Chemspider ID

8148502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9972910

PDB ID

Not Available

ChEBI ID

656980

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1820881

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Gnaphaliin (HMDB0030544)

MOL for HMDB0030544 (Gnaphaliin)

3D MOL for HMDB0030544 (Gnaphaliin)

3D SDF for HMDB0030544 (Gnaphaliin)

3D-SDF for HMDB0030544 (Gnaphaliin)

PDB for HMDB0030544 (Gnaphaliin)

3D PDB for HMDB0030544 (Gnaphaliin)

SMILES for HMDB0030544 (Gnaphaliin)

INCHI for HMDB0030544 (Gnaphaliin)

Structure for HMDB0030544 (Gnaphaliin)

3D Structure for HMDB0030544 (Gnaphaliin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra