Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:16:43 UTC

Update Date

2021-09-26 23:01:38 UTC

HMDB ID

HMDB0250275

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cirsiliol

Description

This compound has been identified in human blood as reported by (PMID: 31557052 ). Cirsiliol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cirsiliol 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

HMDB0250275
     RDKit          3D
Cirsiliol
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.9005   -2.5476   -1.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.3177   -0.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656   -0.4812   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -0.8296   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158    0.0188   -0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -0.3196   -0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616    0.4175   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318   -0.0367   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -1.2840   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -1.7444   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077   -1.0178   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6679   -1.5180   -1.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423    0.2055   -0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3756    0.9375   -0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9573    0.6738   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.6241    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    2.0288    0.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2178    3.1370    1.3689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359    1.2245    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485    1.5616    0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8024    2.7389    1.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919    0.7090    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    1.0986    0.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085    0.7589    1.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -3.3121   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868   -2.4178   -2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -2.9094   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -1.7678   -0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1139   -1.8738   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4074   -2.7089   -1.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7334   -2.4082   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4008    1.8292    0.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8584    1.6387    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    2.2804    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465    3.4509    1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2352    0.0365    1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6268    0.3968    2.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7684    1.7275    2.2764 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 19  5  2  0
 15  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 21 35  1  0
 24 36  1  0
 24 37  1  0
 24 38  1  0
M  END


  Mrv0541 02241214272D          

 24 26  0  0  0  0            999 V2000
   -3.5704    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558    1.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    2.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -0.2061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704   -1.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8572   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8572   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425   -2.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5704    0.2048    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  1  0  0  0  0
  3 12  2  0  0  0  0
  4  5  2  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 20  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 24  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  2  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250275

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3

> <INCHI_KEY>
IMEYGBIXGJLUIS-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.83564045556824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.391346602333333

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.273292203865035

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.567004630558664

> <JCHEM_PKA_STRONGEST_BASIC>
-4.368720009574679

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
85.84030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cirsiliol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250275
     RDKit          3D
Cirsiliol
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.9005   -2.5476   -1.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.3177   -0.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656   -0.4812   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -0.8296   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158    0.0188   -0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -0.3196   -0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616    0.4175   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318   -0.0367   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -1.2840   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -1.7444   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077   -1.0178   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6679   -1.5180   -1.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423    0.2055   -0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3756    0.9375   -0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9573    0.6738   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.6241    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    2.0288    0.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2178    3.1370    1.3689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359    1.2245    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485    1.5616    0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8024    2.7389    1.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919    0.7090    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    1.0986    0.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085    0.7589    1.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -3.3121   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868   -2.4178   -2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -2.9094   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -1.7678   -0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1139   -1.8738   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4074   -2.7089   -1.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7334   -2.4082   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4008    1.8292    0.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8584    1.6387    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    2.2804    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465    3.4509    1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2352    0.0365    1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6268    0.3968    2.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7684    1.7275    2.2764 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 19  5  2  0
 15  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 21 35  1  0
 24 36  1  0
 24 37  1  0
 24 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.665   1.924   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.331   2.694   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.999   1.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.999   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.665  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.331   0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -0.385   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   2.694   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.331   1.924   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.665   2.694   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.665   4.233   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.331  -0.385   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   4.233   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.665  -2.694   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.333  -1.924   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.333  -0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.999   0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.665  -0.385   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.665  -1.924   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.999  -2.694   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.999  -4.233   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.665   0.382   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11    6   10   12                                                  
CONECT   12    3   11   13                                                  
CONECT   13   12                                                            
CONECT   14    4   24                                                       
CONECT   15   10                                                            
CONECT   16   17                                                            
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    8   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   17   21   23                                                  
CONECT   23   22                                                            
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0250275
HETATM    1  C1  UNL     1      -3.900  -2.548  -1.220  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.233  -1.318  -0.605  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.166  -0.481  -0.250  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.857  -0.830  -0.483  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.816   0.019  -0.120  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.430  -0.320  -0.346  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.462   0.417  -0.037  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.832  -0.037  -0.324  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.008  -1.284  -0.940  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.271  -1.744  -1.226  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.408  -1.018  -0.927  1.00  0.00           C  
HETATM   12  O3  UNL     1       6.668  -1.518  -1.232  1.00  0.00           O  
HETATM   13  C10 UNL     1       5.242   0.205  -0.323  1.00  0.00           C  
HETATM   14  O4  UNL     1       6.376   0.937  -0.022  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.957   0.674  -0.033  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.222   1.624   0.562  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.083   2.029   0.823  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.218   3.137   1.369  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.136   1.225   0.482  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.449   1.562   0.710  1.00  0.00           C  
HETATM   21  O6  UNL     1      -2.802   2.739   1.300  1.00  0.00           O  
HETATM   22  C16 UNL     1      -3.492   0.709   0.345  1.00  0.00           C  
HETATM   23  O7  UNL     1      -4.799   1.099   0.598  1.00  0.00           O  
HETATM   24  C17 UNL     1      -5.409   0.759   1.831  1.00  0.00           C  
HETATM   25  H1  UNL     1      -3.559  -3.312  -0.491  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.187  -2.418  -2.069  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.851  -2.909  -1.710  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.608  -1.768  -0.952  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.114  -1.874  -1.184  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.407  -2.709  -1.702  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.733  -2.408  -1.668  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.401   1.829   0.411  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.858   1.639   0.441  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.053   2.280   0.842  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.247   3.451   1.620  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.235   0.036   1.720  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.627   0.397   2.534  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.768   1.728   2.276  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   28
CONECT    5    6   19   19
CONECT    6    7
CONECT    7    8   16   16
CONECT    8    9    9   15
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12   13
CONECT   12   31
CONECT   13   14   15   15
CONECT   14   32
CONECT   15   33
CONECT   16   17   34
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   22   22
CONECT   21   35
CONECT   22   23
CONECT   23   24
CONECT   24   36   37   38
END

HMDB0250275
     RDKit          3D
Cirsiliol
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.9005   -2.5476   -1.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.3177   -0.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656   -0.4812   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -0.8296   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158    0.0188   -0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -0.3196   -0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616    0.4175   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318   -0.0367   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -1.2840   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -1.7444   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077   -1.0178   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6679   -1.5180   -1.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423    0.2055   -0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3756    0.9375   -0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9573    0.6738   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.6241    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    2.0288    0.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2178    3.1370    1.3689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359    1.2245    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485    1.5616    0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8024    2.7389    1.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919    0.7090    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    1.0986    0.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085    0.7589    1.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -3.3121   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868   -2.4178   -2.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -2.9094   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -1.7678   -0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1139   -1.8738   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4074   -2.7089   -1.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7334   -2.4082   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4008    1.8292    0.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8584    1.6387    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    2.2804    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465    3.4509    1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2352    0.0365    1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6268    0.3968    2.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7684    1.7275    2.2764 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 19  5  2  0
 15  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 21 35  1  0
 24 36  1  0
 24 37  1  0
 24 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3',4',5-Trihydroxy-6,7-dimethoxyflavone	ChEBI
6,7-Dimethoxy-5,3',4'-trihydroxyflavone	ChEBI
3',4',5-Trihydroxy-6,7-dimethoxy-flavone	MeSH

Chemical Formula

C₁₇H₁₄O₇

Average Molecular Weight

330.2889

Monoisotopic Molecular Weight

330.073952802

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

Traditional Name

cirsiliol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC

InChI Identifier

InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3

InChI Key

IMEYGBIXGJLUIS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:3719 )
dimethoxyflavone (CHEBI:3719 )
flavones (C10033 )
Flavones and Flavonols (C10033 )
Flavones and Flavonols (LMPK12111227 )

Ontology

Not Available

Exogenous (FooDB: )

Food

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)
Common sage (FooDB: FOOD00165)

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	3.05	ALOGPS
logP	2.39	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.84 m³·mol⁻¹	ChemAxon
Polarizability	32.84 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]+	174.431	30932474
DeepCCS	[M-H]-	172.073	30932474
DeepCCS	[M-2H]-	206.274	30932474
DeepCCS	[M+Na]+	181.631	30932474
AllCCS	[M+H]+	176.0	32859911
AllCCS	[M+H-H2O]+	172.5	32859911
AllCCS	[M+NH4]+	179.2	32859911
AllCCS	[M+Na]+	180.1	32859911
AllCCS	[M-H]-	176.6	32859911
AllCCS	[M+Na-2H]-	176.2	32859911
AllCCS	[M+HCOO]-	175.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.1569 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2194.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	245.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	545.5 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	554.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	947.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	432.7 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	1411.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	426.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	211.1 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	136.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cirsiliol	COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC	4974.5	Standard polar	33892256
Cirsiliol	COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC	3272.2	Standard non polar	33892256
Cirsiliol	COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC	3374.1	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 - Cirsiliol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w29-0529000000-657bcbdce3c33c05fa19	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cirsiliol 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 - Cirsiliol 10V, Positive-QTOF	splash10-001i-0009000000-6fdb0b39524682572668	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 20V, Positive-QTOF	splash10-001i-0029000000-e2443fa738a37a6c94c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 40V, Positive-QTOF	splash10-0a59-2591000000-273c2d09d171c9c377a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 10V, Negative-QTOF	splash10-004i-0009000000-180fc64ac4527a869911	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 20V, Negative-QTOF	splash10-004i-0039000000-e18384ff2ececeea4c40	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 40V, Negative-QTOF	splash10-00dl-7591000000-cff288ef73ebd280eb74	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 10V, Positive-QTOF	splash10-001i-0009000000-6e7c1f722f7f2751ab68	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 20V, Positive-QTOF	splash10-001i-0009000000-974e87f7b29a2112831c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 40V, Positive-QTOF	splash10-000i-0294000000-8a78f0a808bb3fa6abe8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 10V, Negative-QTOF	splash10-004i-0009000000-3ed9b5835e6e53d95cde	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsiliol 20V, Negative-QTOF	splash10-01ti-0049000000-97f6ef43a008bb11d3f9	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

FDB016700

KNApSAcK ID

C00001033

Chemspider ID

Not Available

KEGG Compound ID

C10033

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160237

PDB ID

Not Available

ChEBI ID

3719

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 Cirsiliol (HMDB0250275)

MOL for HMDB0250275 (Cirsiliol)

3D MOL for HMDB0250275 (Cirsiliol)

3D SDF for HMDB0250275 (Cirsiliol)

3D-SDF for HMDB0250275 (Cirsiliol)

PDB for HMDB0250275 (Cirsiliol)

3D PDB for HMDB0250275 (Cirsiliol)

SMILES for HMDB0250275 (Cirsiliol)

INCHI for HMDB0250275 (Cirsiliol)

Structure for HMDB0250275 (Cirsiliol)

3D Structure for HMDB0250275 (Cirsiliol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra