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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 04:06:36 UTC

Update Date

2021-09-26 23:00:34 UTC

HMDB ID

HMDB0249594

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Capillarisin

Description

5,7-dihydroxy-2-(4-hydroxyphenoxy)-6-methoxy-4H-chromen-4-one belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Based on a literature review very few articles have been published on 5,7-dihydroxy-2-(4-hydroxyphenoxy)-6-methoxy-4H-chromen-4-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Capillarisin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Capillarisin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249594
     RDKit          3D
Capillarisin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.6518    0.6501    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403   -0.5608    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433   -0.4700    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -0.1560    1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.0667    2.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -0.0755    1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130   -0.3000   -0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -0.2126   -0.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -0.4098   -1.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4904   -0.3294   -1.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153   -0.0362   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551    1.2870   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6831    1.6657    0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813    0.6885    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2230    1.0352    2.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9372   -0.6269    1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -0.9842    0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521   -0.7205   -2.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0179   -0.8282   -2.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -1.1103   -3.4715 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270   -0.6084   -1.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -0.6962   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -1.0118   -2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    0.4720    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4595    1.0527   -0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274    1.4532    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -0.0066    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768    0.1682    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    2.0760   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425    2.6989    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    1.2475    3.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128   -1.3920    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -2.0288   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -0.8921   -3.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7335   -1.1053   -2.2795 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 21  7  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 23 35  1  0
M  END

  Mrv1533004231521072D          

 23 25  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249594

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2OC(OC3=CC=C(O)C=C3)=CC(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-21-16-11(19)6-12-14(15(16)20)10(18)7-13(23-12)22-9-4-2-8(17)3-5-9/h2-7,17,19-20H,1H3

> <INCHI_KEY>
NTKNGUAZSFAKEE-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.937286456722948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenoxy)-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.190947400666666

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.568565285526997

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.029771562452788

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7620335370753075

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
89.23240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
capillarisin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249594
     RDKit          3D
Capillarisin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.6518    0.6501    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403   -0.5608    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433   -0.4700    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -0.1560    1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.0667    2.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -0.0755    1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130   -0.3000   -0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -0.2126   -0.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -0.4098   -1.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4904   -0.3294   -1.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153   -0.0362   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551    1.2870   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6831    1.6657    0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813    0.6885    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2230    1.0352    2.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9372   -0.6269    1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -0.9842    0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521   -0.7205   -2.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0179   -0.8282   -2.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -1.1103   -3.4715 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270   -0.6084   -1.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -0.6962   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -1.0118   -2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    0.4720    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4595    1.0527   -0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274    1.4532    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -0.0066    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768    0.1682    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    2.0760   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425    2.6989    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    1.2475    3.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128   -1.3920    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -2.0288   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -0.8921   -3.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7335   -1.1053   -2.2795 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 21  7  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
CONECT   16    9   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0249594
HETATM    1  C1  UNL     1       5.652   0.650   0.034  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.940  -0.561   0.252  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.543  -0.470   0.115  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.781  -0.156   1.230  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.376   0.067   2.465  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.414  -0.075   1.058  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.813  -0.300  -0.187  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.505  -0.213  -0.309  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.134  -0.410  -1.442  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.490  -0.329  -1.611  1.00  0.00           O  
HETATM   11  C7  UNL     1      -3.415  -0.036  -0.652  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.755   1.287  -0.457  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.683   1.666   0.494  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.281   0.688   1.264  1.00  0.00           C  
HETATM   15  O5  UNL     1      -6.223   1.035   2.233  1.00  0.00           O  
HETATM   16  C11 UNL     1      -4.937  -0.627   1.063  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.018  -0.984   0.118  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.352  -0.721  -2.535  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.018  -0.828  -2.485  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.742  -1.110  -3.471  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.627  -0.608  -1.257  1.00  0.00           C  
HETATM   22  C16 UNL     1       3.004  -0.696  -1.114  1.00  0.00           C  
HETATM   23  O7  UNL     1       3.735  -1.012  -2.249  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.740   0.472   0.137  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.460   1.053  -0.994  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.327   1.453   0.730  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.382  -0.007   2.529  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.777   0.168   1.906  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.305   2.076  -1.043  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.943   2.699   0.640  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.003   1.247   3.185  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.413  -1.392   1.673  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.777  -2.029  -0.006  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.830  -0.892  -3.495  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.734  -1.105  -2.279  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5    6
CONECT    5   27
CONECT    6    7    7   28
CONECT    7    8   21
CONECT    8    9
CONECT    9   10   18   18
CONECT   10   11
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   16
CONECT   15   31
CONECT   16   17   17   32
CONECT   17   33
CONECT   18   19   34
CONECT   19   20   20   21
CONECT   21   22   22
CONECT   22   23
CONECT   23   35
END

HMDB0249594
     RDKit          3D
Capillarisin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.6518    0.6501    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403   -0.5608    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433   -0.4700    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -0.1560    1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.0667    2.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -0.0755    1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130   -0.3000   -0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -0.2126   -0.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -0.4098   -1.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4904   -0.3294   -1.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153   -0.0362   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551    1.2870   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6831    1.6657    0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813    0.6885    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2230    1.0352    2.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9372   -0.6269    1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -0.9842    0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521   -0.7205   -2.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0179   -0.8282   -2.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -1.1103   -3.4715 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270   -0.6084   -1.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -0.6962   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -1.0118   -2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    0.4720    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4595    1.0527   -0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274    1.4532    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -0.0066    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768    0.1682    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    2.0760   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425    2.6989    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    1.2475    3.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128   -1.3920    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -2.0288   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -0.8921   -3.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7335   -1.1053   -2.2795 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 21  7  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 23 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Capillarisine	MeSH

Chemical Formula

C₁₆H₁₂O₇

Average Molecular Weight

316.265

Monoisotopic Molecular Weight

316.058302726

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenoxy)-6-methoxy-4H-chromen-4-one

Traditional Name

capillarisin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2OC(OC3=CC=C(O)C=C3)=CC(=O)C2=C1O

InChI Identifier

InChI=1S/C16H12O7/c1-21-16-11(19)6-12-14(15(16)20)10(18)7-13(23-12)22-9-4-2-8(17)3-5-9/h2-7,17,19-20H,1H3

InChI Key

NTKNGUAZSFAKEE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Chromone
Coumarin
Diaryl ether
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous ester
Heteroaromatic compound
Vinylogous acid
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:3368 )
chromones (C08999 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.18	ALOGPS
logP	3.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.03	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.23 m³·mol⁻¹	ChemAxon
Polarizability	29.94 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]+	174.663	30932474
DeepCCS	[M-H]-	172.305	30932474
DeepCCS	[M-2H]-	206.509	30932474
DeepCCS	[M+Na]+	182.031	30932474
AllCCS	[M+H]+	171.2	32859911
AllCCS	[M+H-H2O]+	167.8	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	172.7	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	171.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Capillarisin	COC1=C(O)C=C2OC(OC3=CC=C(O)C=C3)=CC(=O)C2=C1O	4915.5	Standard polar	33892256
Capillarisin	COC1=C(O)C=C2OC(OC3=CC=C(O)C=C3)=CC(=O)C2=C1O	3059.9	Standard non polar	33892256
Capillarisin	COC1=C(O)C=C2OC(OC3=CC=C(O)C=C3)=CC(=O)C2=C1O	3065.7	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 - Capillarisin GC-MS (Non-derivatized) - 70eV, Positive	splash10-08g0-1921000000-dee0e44a144b1b4213d9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capillarisin GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capillarisin 10V, Positive-QTOF	splash10-014i-0009000000-86072cf41042a798319c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capillarisin 20V, Positive-QTOF	splash10-014i-0009000000-f3aaa8c4866caaf47d9c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capillarisin 40V, Positive-QTOF	splash10-0002-0390000000-154c8e9ec306907b33bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capillarisin 10V, Negative-QTOF	splash10-014i-0009000000-9039cd212321ec38115d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capillarisin 20V, Negative-QTOF	splash10-014i-0197000000-272fba3c545a7752d60c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capillarisin 40V, Negative-QTOF	splash10-0aor-6950000000-f4d903200f0fed1ea8d9	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00002420

Chemspider ID

4444711

KEGG Compound ID

C08999

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Capillarisin (HMDB0249594)

MOL for HMDB0249594 (Capillarisin)

3D MOL for HMDB0249594 (Capillarisin)

3D SDF for HMDB0249594 (Capillarisin)

3D-SDF for HMDB0249594 (Capillarisin)

PDB for HMDB0249594 (Capillarisin)

3D PDB for HMDB0249594 (Capillarisin)

SMILES for HMDB0249594 (Capillarisin)

INCHI for HMDB0249594 (Capillarisin)

Structure for HMDB0249594 (Capillarisin)

3D Structure for HMDB0249594 (Capillarisin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra