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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:15:12 UTC

Update Date

2021-09-23 20:15:12 UTC

HMDB ID

HMDB0302736

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Chrysosplenol

Description

Chrysosplenol, also known as quercetagetin 3,7,3'-trimethyl ether or 4',5,6-trihydroxy-3,3',7-trimethoxyflavone, 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, chrysosplenol is considered to be a flavonoid lipid molecule. Chrysosplenol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Chrysosplenol can be found in german camomile, which makes chrysosplenol a potential biomarker for the consumption of this food product.

Structure

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


  Mrv0541 02241221262D          

 26 28  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   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
    2.8579    0.8250    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 26  1  0  0  0  0
M  END

HMDB0302736
     RDKit          3D
Chrysosplenol
 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.4016    0.4594   -1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024   -0.8909   -0.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   -1.3076   -0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -0.4161   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615   -0.8250   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875    0.0281   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -0.6118   -0.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -0.0016   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861   -0.7612   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859   -0.1261   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4556   -0.8688    0.0520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4343   -2.2609    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745    1.2591   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197    1.8747   -0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2319    1.9969   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2927    3.3763   -0.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    1.3749   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191    2.0483   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8646    3.2934   -0.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    1.3895   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5332    2.1268   -0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007    2.7082    0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247   -2.1569    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -3.0261    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -2.6107    0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8638   -3.4606    0.1857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9469    1.1406   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082    0.5858   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4678    0.6877   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.5766   -0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001   -1.8331    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857   -2.6124    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0819   -2.6836   -0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7965   -2.5867    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4661    1.3066   -0.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    3.8933   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200    3.7562    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824    2.6889    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0707    2.1145    1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4212   -2.5064    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615   -4.0476    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7749   -3.0918   -0.0510 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  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 20  6  2  0
 17  8  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 26 42  1  0
M  END


  Mrv0541 02241221262D          

 26 28  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   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
    2.8579    0.8250    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302736

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C(O)=C(OC)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O8/c1-23-10-6-8(4-5-9(10)19)17-18(25-3)16(22)13-11(26-17)7-12(24-2)14(20)15(13)21/h4-7,19-21H,1-3H3

> <INCHI_KEY>
QQBSPLCHDUCBNM-UHFFFAOYSA-N

> <FORMULA>
C18H16O8

> <MOLECULAR_WEIGHT>
360.3148

> <EXACT_MASS>
360.084517488

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.60826486048376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.2573496436666662

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.157641928115149

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.439667205318107

> <JCHEM_PKA_STRONGEST_BASIC>
-4.421939067793229

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
92.55890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chrysosplenol C

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302736
     RDKit          3D
Chrysosplenol
 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.4016    0.4594   -1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024   -0.8909   -0.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   -1.3076   -0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -0.4161   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615   -0.8250   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875    0.0281   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -0.6118   -0.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -0.0016   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861   -0.7612   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859   -0.1261   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4556   -0.8688    0.0520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4343   -2.2609    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745    1.2591   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197    1.8747   -0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2319    1.9969   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2927    3.3763   -0.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    1.3749   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191    2.0483   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8646    3.2934   -0.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    1.3895   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5332    2.1268   -0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007    2.7082    0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247   -2.1569    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -3.0261    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -2.6107    0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8638   -3.4606    0.1857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9469    1.1406   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082    0.5858   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4678    0.6877   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.5766   -0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001   -1.8331    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857   -2.6124    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0819   -2.6836   -0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7965   -2.5867    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4661    1.3066   -0.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    3.8933   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200    3.7562    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824    2.6889    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0707    2.1145    1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4212   -2.5064    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615   -4.0476    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7749   -3.0918   -0.0510 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  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 20  6  2  0
 17  8  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 26 42  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       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   19                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9                                                       
CONECT   20   16   21                                                       
CONECT   21   20                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24   10   25                                                       
CONECT   25   24                                                            
CONECT   26    4                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0302736
HETATM    1  C1  UNL     1      -5.402   0.459  -1.052  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.202  -0.891  -0.623  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.910  -1.308  -0.319  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.834  -0.416  -0.433  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.561  -0.825  -0.133  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.388   0.028  -0.171  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.796  -0.612  -0.088  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.927  -0.002  -0.109  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.086  -0.761  -0.017  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.286  -0.126  -0.039  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.456  -0.869   0.052  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.434  -2.261   0.166  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.375   1.259  -0.151  1.00  0.00           C  
HETATM   14  O4  UNL     1       5.620   1.875  -0.170  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.232   1.997  -0.241  1.00  0.00           C  
HETATM   16  O5  UNL     1       3.293   3.376  -0.353  1.00  0.00           O  
HETATM   17  C12 UNL     1       2.018   1.375  -0.221  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.819   2.048  -0.305  1.00  0.00           C  
HETATM   19  O6  UNL     1       0.865   3.293  -0.407  1.00  0.00           O  
HETATM   20  C14 UNL     1      -0.408   1.390  -0.282  1.00  0.00           C  
HETATM   21  O7  UNL     1      -1.533   2.127  -0.360  1.00  0.00           O  
HETATM   22  C15 UNL     1      -2.201   2.708   0.757  1.00  0.00           C  
HETATM   23  C16 UNL     1      -1.425  -2.157   0.280  1.00  0.00           C  
HETATM   24  C17 UNL     1      -2.486  -3.026   0.389  1.00  0.00           C  
HETATM   25  C18 UNL     1      -3.763  -2.611   0.088  1.00  0.00           C  
HETATM   26  O8  UNL     1      -4.864  -3.461   0.186  1.00  0.00           O  
HETATM   27  H1  UNL     1      -4.947   1.141  -0.289  1.00  0.00           H  
HETATM   28  H2  UNL     1      -4.908   0.586  -2.030  1.00  0.00           H  
HETATM   29  H3  UNL     1      -6.468   0.688  -1.182  1.00  0.00           H  
HETATM   30  H4  UNL     1      -3.051   0.577  -0.787  1.00  0.00           H  
HETATM   31  H5  UNL     1       3.000  -1.833   0.069  1.00  0.00           H  
HETATM   32  H6  UNL     1       6.486  -2.612   0.298  1.00  0.00           H  
HETATM   33  H7  UNL     1       5.082  -2.684  -0.795  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.797  -2.587   1.030  1.00  0.00           H  
HETATM   35  H9  UNL     1       6.466   1.307  -0.102  1.00  0.00           H  
HETATM   36  H10 UNL     1       4.146   3.893  -0.374  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.920   3.756   0.921  1.00  0.00           H  
HETATM   38  H12 UNL     1      -3.282   2.689   0.508  1.00  0.00           H  
HETATM   39  H13 UNL     1      -2.071   2.115   1.675  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.421  -2.506   0.526  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.362  -4.048   0.710  1.00  0.00           H  
HETATM   42  H16 UNL     1      -5.775  -3.092  -0.051  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   30
CONECT    5    6   23   23
CONECT    6    7   20   20
CONECT    7    8
CONECT    8    9    9   17
CONECT    9   10   31
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   32   33   34
CONECT   13   14   15
CONECT   14   35
CONECT   15   16   17   17
CONECT   16   36
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22
CONECT   22   37   38   39
CONECT   23   24   40
CONECT   24   25   25   41
CONECT   25   26
CONECT   26   42
END

HMDB0302736
     RDKit          3D
Chrysosplenol
 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.4016    0.4594   -1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024   -0.8909   -0.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   -1.3076   -0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -0.4161   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615   -0.8250   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875    0.0281   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -0.6118   -0.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -0.0016   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861   -0.7612   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859   -0.1261   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4556   -0.8688    0.0520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4343   -2.2609    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745    1.2591   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197    1.8747   -0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2319    1.9969   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2927    3.3763   -0.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    1.3749   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191    2.0483   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8646    3.2934   -0.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    1.3895   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5332    2.1268   -0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007    2.7082    0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247   -2.1569    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -3.0261    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -2.6107    0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8638   -3.4606    0.1857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9469    1.1406   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082    0.5858   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4678    0.6877   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.5766   -0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001   -1.8331    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857   -2.6124    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0819   -2.6836   -0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7965   -2.5867    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4661    1.3066   -0.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    3.8933   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200    3.7562    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824    2.6889    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0707    2.1145    1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4212   -2.5064    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615   -4.0476    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7749   -3.0918   -0.0510 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  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 20  6  2  0
 17  8  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 26 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',5,6-Trihydroxy-3,3',7-trimethoxyflavone	ChEBI
Quercetagetin 3,7,3'-trimethyl ether	ChEBI

Chemical Formula

C₁₈H₁₆O₈

Average Molecular Weight

360.3148

Monoisotopic Molecular Weight

360.084517488

IUPAC Name

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

Traditional Name

chrysosplenol C

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C(O)=C(OC)C=C2O1

InChI Identifier

InChI=1S/C18H16O8/c1-23-10-6-8(4-5-9(10)19)17-18(25-3)16(22)13-11(26-17)7-12(24-2)14(20)15(13)21/h4-7,19-21H,1-3H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:3690 )
trimethoxyflavone (CHEBI:3690 )
flavonols (C10031 )
Flavones and Flavonols (C10031 )
Flavones and Flavonols (LMPK12112982 )
a small molecule (CPD-10520 )

Ontology

Not Available

German camomile (FooDB: FOOD00107)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0302736)

anti inflammatory (HMDB: HMDB0302736)
anti spasmodic (HMDB: HMDB0302736)

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	2.9	ALOGPS
logP	2.26	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.56 m³·mol⁻¹	ChemAxon
Polarizability	35.61 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]+	182.545	32859911
AllCCS	[M+H-H2O]+	179.295	32859911
AllCCS	[M+Na]+	186.417	32859911
AllCCS	[M+NH4]+	185.554	32859911
AllCCS	[M-H]-	183.844	32859911
AllCCS	[M+Na-2H]-	183.443	32859911
AllCCS	[M+HCOO]-	183.151	32859911
DeepCCS	[M+H]+	182.246	30932474
DeepCCS	[M-H]-	179.888	30932474
DeepCCS	[M-2H]-	214.033	30932474
DeepCCS	[M+Na]+	189.261	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 - Chrysosplenol 10V, Positive-QTOF	splash10-03di-0009000000-5170e7840ad4ffef7fcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 20V, Positive-QTOF	splash10-03di-0009000000-535620010cfb75744da8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 40V, Positive-QTOF	splash10-0rl0-0944000000-9d3700c202fea36fdbb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 10V, Negative-QTOF	splash10-0a4i-0009000000-db4d16df96abc4c642d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 20V, Negative-QTOF	splash10-0a4l-0119000000-15f3573902c1c49b4d06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 40V, Negative-QTOF	splash10-06ri-2984000000-c23ed70880e88757005d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 10V, Positive-QTOF	splash10-03di-0009000000-ef0e36da9abfe27aa076	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 20V, Positive-QTOF	splash10-03di-0009000000-97d15839107665ea85c9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 40V, Positive-QTOF	splash10-02ai-2914000000-0c7f0d74550e6932a407	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 10V, Negative-QTOF	splash10-0a4i-0009000000-f8e67485e1c0a329c315	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 20V, Negative-QTOF	splash10-0a4i-0309000000-544d04d93dc0400e76d0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysosplenol 40V, Negative-QTOF	splash10-06e9-1912000000-3cec27af837a13ad4dcf	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

Not Available

METLIN ID

Not Available

PubChem Compound

189065

PDB ID

Not Available

ChEBI ID

3690

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

Not Available

Showing metabocard for Chrysosplenol (HMDB0302736)

MOL for HMDB0302736 (Chrysosplenol)

3D MOL for HMDB0302736 (Chrysosplenol)

3D SDF for HMDB0302736 (Chrysosplenol)

3D-SDF for HMDB0302736 (Chrysosplenol)

PDB for HMDB0302736 (Chrysosplenol)

3D PDB for HMDB0302736 (Chrysosplenol)

SMILES for HMDB0302736 (Chrysosplenol)

INCHI for HMDB0302736 (Chrysosplenol)

Structure for HMDB0302736 (Chrysosplenol)

3D Structure for HMDB0302736 (Chrysosplenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra