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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:30:55 UTC

Update Date

2022-09-22 18:34:56 UTC

HMDB ID

HMDB0029521

Secondary Accession Numbers

HMDB29521

Metabolite Identification

Common Name

Norizalpinin

Description

Norizalpinin, also known as teptochrysin, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, norizalpinin is considered to be a flavonoid. Norizalpinin is found, on average, in the highest concentration within mexican oreganos (Lippia graveolens). Norizalpinin has also been detected, but not quantified in, several different foods, such as cloudberries (Rubus chamaemorus), yellow zucchinis (Cucurbita pepo var. cylindrica), tea leaf willows (Salix pulchra), common thymes (Thymus vulgaris), and pigeon peas (Cajanus cajan). This could make norizalpinin a potential biomarker for the consumption of these foods. Norizalpinin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Norizalpinin.

Structure

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

HMDB0029521
     RDKit          3D
Norizalpinin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.3737   -3.0100   -0.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -1.8444   -0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454   -1.5081   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -2.5178   -0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -0.2472   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252    0.2461   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884   -0.2470   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4684    0.2809   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633    1.3173    0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078    1.8461    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.3194    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185    0.6116    0.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    0.3513    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4038    1.3144    0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7493    1.0708    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6488    2.0887    0.9742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.1714    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -1.1987   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8182   -2.4229   -0.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -0.9209   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -2.6382   -0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694   -1.0130   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988   -0.1497   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6668    1.7269    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7523    2.6691    1.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447    1.7375    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    2.3052    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328    2.6773    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2752   -0.4232    0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532   -3.2502   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  6  1  0
 20 13  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END


  Mrv1652309042000362D          

 20 22  0  0  0  0            999 V2000
    4.2868    0.8250    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
    4.2868    0.0000    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
    3.5724   -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
    2.8579    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
    0.0000   -1.6500    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
    1.4289   -1.6500    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    1.4289    0.0000    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
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029521

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H

> <INCHI_KEY>
VCCRNZQBSJXYJD-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.540984943508562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.7634301073333334

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.955603317080702

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.383248543296597

> <JCHEM_PKA_STRONGEST_BASIC>
-3.877672895331391

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
72.9004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galangin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029521
     RDKit          3D
Norizalpinin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.3737   -3.0100   -0.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -1.8444   -0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454   -1.5081   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -2.5178   -0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -0.2472   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252    0.2461   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884   -0.2470   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4684    0.2809   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633    1.3173    0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078    1.8461    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.3194    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185    0.6116    0.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    0.3513    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4038    1.3144    0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7493    1.0708    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6488    2.0887    0.9742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.1714    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -1.1987   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8182   -2.4229   -0.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -0.9209   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -2.6382   -0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694   -1.0130   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988   -0.1497   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6668    1.7269    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7523    2.6691    1.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447    1.7375    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    2.3052    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328    2.6773    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2752   -0.4232    0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532   -3.2502   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  6  1  0
 20 13  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7    9   11                                                       
CONECT    8    4    5   15                                                  
CONECT    9    6    7   16                                                  
CONECT   10    6   12   17                                                  
CONECT   11    7   12   20                                                  
CONECT   12   10   11   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   19                                                  
CONECT   15    8   14   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0029521
HETATM    1  O1  UNL     1      -1.374  -3.010  -0.757  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.052  -1.844  -0.459  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.345  -1.508  -0.491  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.161  -2.518  -0.834  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.751  -0.247  -0.178  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.125   0.246  -0.165  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.188  -0.247  -0.845  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.468   0.281  -0.661  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.663   1.317   0.219  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.608   1.846   0.926  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.375   1.319   0.734  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.218   0.612   0.153  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.483   0.351   0.196  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.404   1.314   0.551  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.749   1.071   0.606  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.649   2.089   0.974  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.230  -0.171   0.300  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.323  -1.199  -0.072  1.00  0.00           C  
HETATM   19  O5  UNL     1      -3.818  -2.423  -0.371  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.983  -0.921  -0.116  1.00  0.00           C  
HETATM   21  H1  UNL     1       2.084  -2.638  -0.901  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.069  -1.013  -1.575  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.299  -0.150  -1.231  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.667   1.727   0.359  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.752   2.669   1.626  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.545   1.738   1.293  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.058   2.305   0.798  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.033   2.677   0.232  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.275  -0.423   0.325  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.453  -3.250  -0.637  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4    5    5
CONECT    4   21
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   26
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   27
CONECT   15   16   17   17
CONECT   16   28
CONECT   17   18   29
CONECT   18   19   20   20
CONECT   19   30
END

HMDB0029521
     RDKit          3D
Norizalpinin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.3737   -3.0100   -0.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -1.8444   -0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454   -1.5081   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -2.5178   -0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -0.2472   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252    0.2461   -0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1884   -0.2470   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4684    0.2809   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633    1.3173    0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078    1.8461    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.3194    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185    0.6116    0.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    0.3513    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4038    1.3144    0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7493    1.0708    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6488    2.0887    0.9742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.1714    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -1.1987   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8182   -2.4229   -0.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -0.9209   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -2.6382   -0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694   -1.0130   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988   -0.1497   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6668    1.7269    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7523    2.6691    1.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447    1.7375    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    2.3052    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328    2.6773    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2752   -0.4232    0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532   -3.2502   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  6  1  0
 20 13  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5,7-Trihydroxy-2-phenyl-4H-benzopyran-4-one	ChEBI
3,5,7-Trihydroxyflavone	ChEBI
3,5,7-TriOH-flavone	ChEBI
Teptochrysin	ChEBI
3,5,7-Trihydroxy-2-phenyl-4-benzopyrone	HMDB
3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one	HMDB
3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9ci	HMDB
3,5,7-Trihydroxy-2-phenyl-4H-chromen-4-one	HMDB
3,5,7-Trihydroxy-flavone	HMDB
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl- (9ci)	HMDB
5,7-Dihydroxyflavonol	HMDB
Galangin	HMDB
Norizalpinin	ChEBI

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.2369

Monoisotopic Molecular Weight

270.05282343

IUPAC Name

3,5,7-trihydroxy-2-phenyl-4H-chromen-4-one

Traditional Name

galangin

CAS Registry Number

548-83-4

SMILES

OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C1

InChI Identifier

InChI=1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H

InChI Key

VCCRNZQBSJXYJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:5262 )
7-hydroxyflavonol (CHEBI:5262 )
Flavones and Flavonols (C10044 )
Flavones and Flavonols (LMPK12111653 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	217 - 218 °C	Not Available
Boiling Point	518.64 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	571.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.322 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	154.914	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001413

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.76	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.9 m³·mol⁻¹	ChemAxon
Polarizability	26.54 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
DeepCCS	[M+H]+	161.752	30932474
DeepCCS	[M-H]-	159.394	30932474
DeepCCS	[M-2H]-	192.28	30932474
DeepCCS	[M+Na]+	167.845	30932474
AllCCS	[M+H]+	160.7	32859911
AllCCS	[M+H-H2O]+	156.7	32859911
AllCCS	[M+NH4]+	164.4	32859911
AllCCS	[M+Na]+	165.4	32859911
AllCCS	[M-H]-	160.2	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	158.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.8 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9776 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2652.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	403.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	508.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	642.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	704.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1214.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	488.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1547.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	489.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	468.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	188.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	148.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norizalpinin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C1	4001.1	Standard polar	33892256
Norizalpinin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C1	2483.1	Standard non polar	33892256
Norizalpinin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=CC=C2)=C1	2734.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norizalpinin,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C1	2819.6	Semi standard non polar	33892256
Norizalpinin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC=CC=C1)O2	2765.4	Semi standard non polar	33892256
Norizalpinin,1TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O)=C2C1=O	2735.1	Semi standard non polar	33892256
Norizalpinin,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C1	2792.2	Semi standard non polar	33892256
Norizalpinin,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=CC=C3)OC2=C1	2728.1	Semi standard non polar	33892256
Norizalpinin,2TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O	2698.5	Semi standard non polar	33892256
Norizalpinin,3TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=CC=C3)OC2=C1	2785.0	Semi standard non polar	33892256
Norizalpinin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C1	3068.7	Semi standard non polar	33892256
Norizalpinin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC=CC=C1)O2	3030.0	Semi standard non polar	33892256
Norizalpinin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O)=C2C1=O	2998.7	Semi standard non polar	33892256
Norizalpinin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC=CC=C3)OC2=C1	3280.4	Semi standard non polar	33892256
Norizalpinin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC=CC=C3)OC2=C1	3215.4	Semi standard non polar	33892256
Norizalpinin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3209.5	Semi standard non polar	33892256
Norizalpinin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC=CC=C3)OC2=C1	3429.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Galangin

METLIN ID

Not Available

PubChem Compound

5281616

PDB ID

Not Available

ChEBI ID

5262

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1247821

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Norizalpinin → 6-[(3,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-5-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Norizalpinin → 6-[(3,5-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Norizalpinin → 6-[(5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Norizalpinin (HMDB0029521)

MOL for HMDB0029521 (Norizalpinin)

3D MOL for HMDB0029521 (Norizalpinin)

3D SDF for HMDB0029521 (Norizalpinin)

3D-SDF for HMDB0029521 (Norizalpinin)

PDB for HMDB0029521 (Norizalpinin)

3D PDB for HMDB0029521 (Norizalpinin)

SMILES for HMDB0029521 (Norizalpinin)

INCHI for HMDB0029521 (Norizalpinin)

Structure for HMDB0029521 (Norizalpinin)

3D Structure for HMDB0029521 (Norizalpinin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions