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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:15:27 UTC

Update Date

2021-09-24 03:15:27 UTC

HMDB ID

HMDB0303612

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cirsilineol

Description

Cirsilineol, also known as 4',5-dihydroxy-3',6,7-trimethoxy-flavone or anisomelin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, cirsilineol is considered to be a flavonoid lipid molecule. Cirsilineol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsilineol can be found in a number of food items such as common thyme, tarragon, common sage, and hyssop, which makes cirsilineol a potential biomarker for the consumption of these food products. Cirsilineol is a bioactive flavone isolated from Artemisia and from Teucrium gnaphalodes .

Structure

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

HMDB0303612
     RDKit          3D
Cirsilineol
 41 43  0  0  0  0  0  0  0  0999 V2000
    5.7415   -1.8682    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8360   -0.7004   -0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -0.0055   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4541   -0.4747   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.2043   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -0.2469   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413   -1.3703    0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -1.7102    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6543   -2.7355    1.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352   -0.9449    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -1.2506    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -2.3331    1.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -0.4113    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1829   -0.7116    0.7348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7535   -0.1593    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.6986   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6638    1.5095   -0.8028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3341    2.6371   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3166    0.9891   -0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820    0.1653   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452    0.4623   -0.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    1.3426   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    1.7846   -1.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681    1.1194   -1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1389    1.5595   -1.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1394   -1.7275    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7708   -2.1268    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3337   -2.7097    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306   -1.3848    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -1.9723    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610   -3.0541    2.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0489   -0.1770    2.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920    0.8866    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6450   -0.7387    2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2298    3.2556   -1.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.3570   -2.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    3.2513   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629    1.8485   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    1.8808   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975    2.6714   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2898    2.3662   -2.2176 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  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21  6  1  0
 20 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 12 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 22 39  1  0
 23 40  1  0
 25 41  1  0
M  END


  Mrv0541 02241219012D          

 25 27  0  0  0  0            999 V2000
   -1.4280    2.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    0.4123    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
   -2.8562    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -2.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708    1.2370    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
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8 25  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
 12 13  1  0  0  0  0
 12 20  1  0  0  0  0
 14 15  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
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303612

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

> <INCHI_KEY>
VKOSQMWSWLZQPA-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.3154

> <EXACT_MASS>
344.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
34.93525892149046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.5372406583333333

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.471368644422

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.866247934618931

> <JCHEM_PKA_STRONGEST_BASIC>
-4.368720010472823

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
90.3226

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cirsilineol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303612
     RDKit          3D
Cirsilineol
 41 43  0  0  0  0  0  0  0  0999 V2000
    5.7415   -1.8682    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8360   -0.7004   -0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -0.0055   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4541   -0.4747   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.2043   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -0.2469   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413   -1.3703    0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -1.7102    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6543   -2.7355    1.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352   -0.9449    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -1.2506    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -2.3331    1.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -0.4113    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1829   -0.7116    0.7348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7535   -0.1593    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.6986   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6638    1.5095   -0.8028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3341    2.6371   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3166    0.9891   -0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820    0.1653   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452    0.4623   -0.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    1.3426   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    1.7846   -1.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681    1.1194   -1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1389    1.5595   -1.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1394   -1.7275    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7708   -2.1268    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3337   -2.7097    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306   -1.3848    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -1.9723    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610   -3.0541    2.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0489   -0.1770    2.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920    0.8866    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6450   -0.7387    2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2298    3.2556   -1.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.3570   -2.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    3.2513   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629    1.8485   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    1.8808   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975    2.6714   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2898    2.3662   -2.2176 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  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21  6  1  0
 20 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 12 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 22 39  1  0
 23 40  1  0
 25 41  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  O   UNK     0      -2.666   4.618   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.666   3.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.332   2.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.332   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.666   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.000   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.000   2.309   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.331   3.079   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   4.618   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   3.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.331   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.331  -1.539   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.666  -2.309   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.334  -1.539   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.334   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.000   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.666   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.666  -1.539   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.000  -2.309   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.000  -3.848   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.334  -4.618   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.666   2.309   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7   25                                                       
CONECT    9   10                                                            
CONECT   10    3    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13    4   12                                                       
CONECT   14    6   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   12   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   17   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    8                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0303612
HETATM    1  C1  UNL     1       5.742  -1.868   0.681  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.836  -0.700  -0.114  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.698  -0.005  -0.496  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.454  -0.475  -0.085  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.326   0.204  -0.457  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.992  -0.247  -0.050  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.841  -1.370   0.719  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.479  -1.710   1.049  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.654  -2.735   1.754  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.535  -0.945   0.613  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.843  -1.251   0.920  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.175  -2.333   1.675  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.862  -0.411   0.431  1.00  0.00           C  
HETATM   14  O4  UNL     1      -5.183  -0.712   0.735  1.00  0.00           O  
HETATM   15  C11 UNL     1      -5.753  -0.159   1.922  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.627   0.699  -0.335  1.00  0.00           C  
HETATM   17  O5  UNL     1      -4.664   1.510  -0.803  1.00  0.00           O  
HETATM   18  C13 UNL     1      -4.334   2.637  -1.588  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.317   0.989  -0.631  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.282   0.165  -0.155  1.00  0.00           C  
HETATM   21  O6  UNL     1      -0.045   0.462  -0.449  1.00  0.00           O  
HETATM   22  C16 UNL     1       2.477   1.343  -1.236  1.00  0.00           C  
HETATM   23  C17 UNL     1       3.717   1.785  -1.629  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.868   1.119  -1.268  1.00  0.00           C  
HETATM   25  O7  UNL     1       6.139   1.560  -1.662  1.00  0.00           O  
HETATM   26  H1  UNL     1       5.139  -1.727   1.591  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.771  -2.127   1.001  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.334  -2.710   0.100  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.431  -1.385   0.531  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.637  -1.972   1.064  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.761  -3.054   2.130  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.049  -0.177   2.764  1.00  0.00           H  
HETATM   33  H8  UNL     1      -6.092   0.887   1.754  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.645  -0.739   2.220  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.230   3.256  -1.801  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.918   2.357  -2.583  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.537   3.251  -1.100  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.063   1.848  -1.230  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.560   1.881  -1.529  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.797   2.671  -2.233  1.00  0.00           H  
HETATM   41  H16 UNL     1       6.290   2.366  -2.218  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   29
CONECT    5    6   22   22
CONECT    6    7    7   21
CONECT    7    8   30
CONECT    8    9    9   10
CONECT   10   11   11   20
CONECT   11   12   13
CONECT   12   31
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   32   33   34
CONECT   16   17   19
CONECT   17   18
CONECT   18   35   36   37
CONECT   19   20   20   38
CONECT   20   21
CONECT   22   23   39
CONECT   23   24   24   40
CONECT   24   25
CONECT   25   41
END

HMDB0303612
     RDKit          3D
Cirsilineol
 41 43  0  0  0  0  0  0  0  0999 V2000
    5.7415   -1.8682    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8360   -0.7004   -0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -0.0055   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4541   -0.4747   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258    0.2043   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -0.2469   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413   -1.3703    0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -1.7102    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6543   -2.7355    1.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352   -0.9449    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -1.2506    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -2.3331    1.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -0.4113    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1829   -0.7116    0.7348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7535   -0.1593    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.6986   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6638    1.5095   -0.8028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3341    2.6371   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3166    0.9891   -0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820    0.1653   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452    0.4623   -0.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    1.3426   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    1.7846   -1.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681    1.1194   -1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1389    1.5595   -1.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1394   -1.7275    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7708   -2.1268    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3337   -2.7097    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306   -1.3848    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -1.9723    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610   -3.0541    2.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0489   -0.1770    2.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920    0.8866    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6450   -0.7387    2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2298    3.2556   -1.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.3570   -2.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    3.2513   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629    1.8485   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    1.8808   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7975    2.6714   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2898    2.3662   -2.2176 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  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 21  6  1  0
 20 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 12 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 22 39  1  0
 23 40  1  0
 25 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anisomelin	MetaCyc
5,4'-Dihydroxy-6,7,3'-trimethoxyflavone	MetaCyc
Eupatrin	MetaCyc
Fastigenin	MetaCyc
5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one	MetaCyc
4',5-Dihydroxy-3',6,7-trimethoxyflavone	MeSH
4',5-Dihydroxy-3',6,7-trimethoxy-flavone	MeSH

Chemical Formula

C₁₈H₁₆O₇

Average Molecular Weight

344.3154

Monoisotopic Molecular Weight

344.089602866

IUPAC Name

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

Traditional Name

cirsilineol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

InChI Key

VKOSQMWSWLZQPA-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:3718 )
trimethoxyflavone (CHEBI:3718 )
flavones (C10032 )
Flavones and Flavonols (C10032 )
Flavones and Flavonols (LMPK12111249 )

Ontology

Not Available

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0303612)
cyclooxygenase 1 inhibitor (HMDB: HMDB0303612)
cyclooxygenase 2 inhibitor (HMDB: HMDB0303612)

Industrial application

Agriculture

Pesticide

Insecticide

parasiticide (HMDB: HMDB0303612)
pesticide (HMDB: HMDB0303612)

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	2.93	ALOGPS
logP	2.54	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.87	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	34.94 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
AllCCS	[M+H]+	179.668	32859911
AllCCS	[M+H-H2O]+	176.314	32859911
AllCCS	[M+Na]+	183.667	32859911
AllCCS	[M+NH4]+	182.775	32859911
AllCCS	[M-H]-	181.287	32859911
AllCCS	[M+Na-2H]-	180.841	32859911
AllCCS	[M+HCOO]-	180.498	32859911
DeepCCS	[M+H]+	177.042	30932474
DeepCCS	[M-H]-	174.684	30932474
DeepCCS	[M-2H]-	208.872	30932474
DeepCCS	[M+Na]+	184.196	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 10V, Positive-QTOF	splash10-0002-0009000000-dc1a431c47b12ff35d6f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 20V, Positive-QTOF	splash10-0002-0009000000-83f5a1606a8c1db30b43	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 40V, Positive-QTOF	splash10-0002-0693000000-2135cd96963ff8bae9a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 10V, Negative-QTOF	splash10-0006-0009000000-d849bd5042cabc197d52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 20V, Negative-QTOF	splash10-0006-0029000000-91a37534990e9343e565	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 40V, Negative-QTOF	splash10-0ar4-0291000000-9206d9f37362017c1a95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 10V, Positive-QTOF	splash10-0002-0009000000-5dc8eb0c39637af07086	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 20V, Positive-QTOF	splash10-0002-0009000000-5dc6fda56294b4fda1a7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 40V, Positive-QTOF	splash10-0udi-0109000000-90d350448efbe259f79b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 10V, Negative-QTOF	splash10-0006-0009000000-72fbd0eb75bc9ea05c55	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cirsilineol 20V, Negative-QTOF	splash10-0f96-0009000000-176ea7d83528de995c1f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cirsilineol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3718

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1486441

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Cirsilineol (HMDB0303612)

MOL for HMDB0303612 (Cirsilineol)

3D MOL for HMDB0303612 (Cirsilineol)

3D SDF for HMDB0303612 (Cirsilineol)

3D-SDF for HMDB0303612 (Cirsilineol)

PDB for HMDB0303612 (Cirsilineol)

3D PDB for HMDB0303612 (Cirsilineol)

SMILES for HMDB0303612 (Cirsilineol)

INCHI for HMDB0303612 (Cirsilineol)

Structure for HMDB0303612 (Cirsilineol)

3D Structure for HMDB0303612 (Cirsilineol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra