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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 07:06:08 UTC

Update Date

2021-09-23 07:06:08 UTC

HMDB ID

HMDB0302154

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gardenin B

Description

Gardenin b, also known as demethyltangeretin or 5-hydroxy-4',6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gardenin b is considered to be a flavonoid lipid molecule. Gardenin b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gardenin b can be found in mandarin orange (clementine, tangerine), peppermint, sweet basil, and winter savory, which makes gardenin b a potential biomarker for the consumption of these food products.

Structure

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


  Mrv0541 02241219462D          

 26 28  0  0  0  0            999 V2000
    1.0719   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157    1.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9294    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -1.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9294   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 24  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 21  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 19 26  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
 24 25  1  0  0  0  0
M  END

HMDB0302154
     RDKit          3D
Gardenin B
 44 46  0  0  0  0  0  0  0  0999 V2000
    7.6890   -0.7010   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -0.8274   -1.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411   -0.5409   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -0.7112   -1.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -0.4493   -1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193    0.0033    0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.2730    0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    0.7246    1.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760    0.9670    2.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764    1.3805    3.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    0.7468    1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049    0.9608    1.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    1.4147    2.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6928    0.7318    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    0.9353    0.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7781   -0.1555    1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    0.2801   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359    0.0340   -1.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    1.1146   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    0.0597   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6300   -0.3941   -2.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -1.7955   -2.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.2936    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696    0.0798   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    0.1716    1.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225   -0.0932    0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6576    0.1275    0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5511   -0.5577   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8602   -1.6588    0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2742   -1.0662   -2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9827   -0.5882   -1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216    0.8979    2.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542    1.5794    3.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2118   -1.1075    1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7106   -0.3482    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0626    0.0100    2.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    0.9576   -3.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605    2.0701   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6771    1.2246   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.0911   -2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -2.3665   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -2.1493   -2.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6044    0.5187    2.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8771    0.0446    1.2650 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
  6 25  1  0
 25 26  2  0
 26  3  1  0
 24  7  1  0
 23 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 25 43  1  0
 26 44  1  0
M  END


  Mrv0541 02241219462D          

 26 28  0  0  0  0            999 V2000
    1.0719   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157    1.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9294    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -1.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9294   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 24  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 21  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 19 26  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
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302154

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3

> <INCHI_KEY>
LXEVSYZNYDZSOB-UHFFFAOYSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.342

> <EXACT_MASS>
358.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.75246169213868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.6831347143333333

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.0474894640964

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.664398426543489

> <JCHEM_PKA_STRONGEST_BASIC>
-4.291547760164282

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
94.8049

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gardenin B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302154
     RDKit          3D
Gardenin B
 44 46  0  0  0  0  0  0  0  0999 V2000
    7.6890   -0.7010   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -0.8274   -1.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411   -0.5409   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -0.7112   -1.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -0.4493   -1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193    0.0033    0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.2730    0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    0.7246    1.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760    0.9670    2.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764    1.3805    3.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    0.7468    1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049    0.9608    1.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    1.4147    2.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6928    0.7318    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    0.9353    0.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7781   -0.1555    1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    0.2801   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359    0.0340   -1.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    1.1146   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    0.0597   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6300   -0.3941   -2.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -1.7955   -2.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.2936    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696    0.0798   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    0.1716    1.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225   -0.0932    0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6576    0.1275    0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5511   -0.5577   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8602   -1.6588    0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2742   -1.0662   -2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9827   -0.5882   -1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216    0.8979    2.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542    1.5794    3.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2118   -1.1075    1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7106   -0.3482    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0626    0.0100    2.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    0.9576   -3.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605    2.0701   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6771    1.2246   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.0911   -2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -2.3665   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -2.1493   -2.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6044    0.5187    2.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8771    0.0446    1.2650 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
  6 25  1  0
 25 26  2  0
 26  3  1  0
 24  7  1  0
 23 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 25 43  1  0
 26 44  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       2.001  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -2.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.336  -3.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.668  -2.694   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.668  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.336  -0.384   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.666   3.464   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.666   1.926   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.666   1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.666  -0.384   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.666  -1.154   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.001  -0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.001   1.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.336   1.926   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.668   1.154   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.003   1.926   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -7.335   1.154   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.336   3.464   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.003  -1.154   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.668  -0.384   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.336  -1.154   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.336  -2.694   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.668  -3.464   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.003  -3.464   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.335  -2.694   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.335  -0.381   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    8                                                            
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13    8   12   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   14                                                            
CONECT   19   20   26                                                       
CONECT   20   15   19   21                                                  
CONECT   21   12   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    4   25                                                       
CONECT   25   24                                                            
CONECT   26   19                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0302154
HETATM    1  C1  UNL     1       7.689  -0.701  -0.472  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.472  -0.827  -1.178  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.241  -0.541  -0.654  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.134  -0.711  -1.461  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.853  -0.449  -1.025  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.619   0.003   0.263  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.255   0.273   0.700  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.951   0.725   1.966  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.376   0.967   2.332  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.676   1.380   3.485  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.372   0.747   1.406  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.705   0.961   1.685  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.094   1.415   2.935  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.693   0.732   0.735  1.00  0.00           C  
HETATM   15  O4  UNL     1      -5.044   0.935   0.979  1.00  0.00           O  
HETATM   16  C12 UNL     1      -5.778  -0.156   1.489  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.299   0.280  -0.507  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.236   0.034  -1.494  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.581   1.115  -2.374  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.975   0.060  -0.808  1.00  0.00           C  
HETATM   21  O6  UNL     1      -1.630  -0.394  -2.069  1.00  0.00           O  
HETATM   22  C16 UNL     1      -1.575  -1.796  -2.267  1.00  0.00           C  
HETATM   23  C17 UNL     1      -0.987   0.294   0.157  1.00  0.00           C  
HETATM   24  O7  UNL     1       0.270   0.080  -0.142  1.00  0.00           O  
HETATM   25  C18 UNL     1       3.724   0.172   1.063  1.00  0.00           C  
HETATM   26  C19 UNL     1       5.022  -0.093   0.623  1.00  0.00           C  
HETATM   27  H1  UNL     1       7.658   0.127   0.273  1.00  0.00           H  
HETATM   28  H2  UNL     1       8.551  -0.558  -1.157  1.00  0.00           H  
HETATM   29  H3  UNL     1       7.860  -1.659   0.061  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.274  -1.066  -2.483  1.00  0.00           H  
HETATM   31  H5  UNL     1       1.983  -0.588  -1.674  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.722   0.898   2.691  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.054   1.579   3.168  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.212  -1.108   1.477  1.00  0.00           H  
HETATM   35  H9  UNL     1      -6.711  -0.348   0.900  1.00  0.00           H  
HETATM   36  H10 UNL     1      -6.063   0.010   2.560  1.00  0.00           H  
HETATM   37  H11 UNL     1      -4.182   0.958  -3.386  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.160   2.070  -2.000  1.00  0.00           H  
HETATM   39  H13 UNL     1      -5.677   1.225  -2.378  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.611  -2.091  -2.718  1.00  0.00           H  
HETATM   41  H15 UNL     1      -1.677  -2.366  -1.326  1.00  0.00           H  
HETATM   42  H16 UNL     1      -2.391  -2.149  -2.937  1.00  0.00           H  
HETATM   43  H17 UNL     1       3.604   0.519   2.067  1.00  0.00           H  
HETATM   44  H18 UNL     1       5.877   0.045   1.265  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   30
CONECT    5    6    6   31
CONECT    6    7   25
CONECT    7    8    8   24
CONECT    8    9   32
CONECT    9   10   10   11
CONECT   11   12   12   23
CONECT   12   13   14
CONECT   13   33
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   34   35   36
CONECT   17   18   20
CONECT   18   19
CONECT   19   37   38   39
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   40   41   42
CONECT   23   24
CONECT   25   26   26   43
CONECT   26   44
END

HMDB0302154
     RDKit          3D
Gardenin B
 44 46  0  0  0  0  0  0  0  0999 V2000
    7.6890   -0.7010   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -0.8274   -1.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411   -0.5409   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -0.7112   -1.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -0.4493   -1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193    0.0033    0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.2730    0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    0.7246    1.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760    0.9670    2.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764    1.3805    3.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717    0.7468    1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049    0.9608    1.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    1.4147    2.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6928    0.7318    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    0.9353    0.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7781   -0.1555    1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    0.2801   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359    0.0340   -1.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    1.1146   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    0.0597   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6300   -0.3941   -2.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -1.7955   -2.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.2936    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696    0.0798   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    0.1716    1.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225   -0.0932    0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6576    0.1275    0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5511   -0.5577   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8602   -1.6588    0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2742   -1.0662   -2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9827   -0.5882   -1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216    0.8979    2.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542    1.5794    3.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2118   -1.1075    1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7106   -0.3482    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0626    0.0100    2.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    0.9576   -3.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605    2.0701   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6771    1.2246   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.0911   -2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -2.3665   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -2.1493   -2.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6044    0.5187    2.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8771    0.0446    1.2650 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
  6 25  1  0
 25 26  2  0
 26  3  1  0
 24  7  1  0
 23 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 25 43  1  0
 26 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-2-(4-methoxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one	ChEBI
5-Hydroxy-4',6,7,8-tetramethoxyflavone	ChEBI
Demethyltangeretin	ChEBI
5-Demethyltangeretin	MeSH

Chemical Formula

C₁₉H₁₈O₇

Average Molecular Weight

358.342

Monoisotopic Molecular Weight

358.10525293

IUPAC Name

5-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

gardenin B

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2O

InChI Identifier

InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3

InChI Key

LXEVSYZNYDZSOB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyflavone (CHEBI:79628 )
tetramethoxyflavone (CHEBI:79628 )
flavones (C15109 )
Flavones and Flavonols (C15109 )
Flavones and Flavonols (LMPK12111451 )

Ontology

Not Available

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Not Available

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	3.07	ALOGPS
logP	2.68	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.66	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.8 m³·mol⁻¹	ChemAxon
Polarizability	36.75 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]+	183.832	32859911
AllCCS	[M+H-H2O]+	180.612	32859911
AllCCS	[M+Na]+	187.667	32859911
AllCCS	[M+NH4]+	186.812	32859911
AllCCS	[M-H]-	186.398	32859911
AllCCS	[M+Na-2H]-	186.107	32859911
AllCCS	[M+HCOO]-	185.938	32859911
DeepCCS	[M+H]+	179.761	30932474
DeepCCS	[M-H]-	177.403	30932474
DeepCCS	[M-2H]-	211.476	30932474
DeepCCS	[M+Na]+	186.704	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 - Gardenin B 10V, Positive-QTOF	splash10-0a4i-0009000000-94235dbf8f75c99fbd22	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 20V, Positive-QTOF	splash10-0a4i-0009000000-927ca53e683bc4ba6953	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 40V, Positive-QTOF	splash10-03di-0259000000-dea961e95f28fe0273c2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 10V, Negative-QTOF	splash10-0a4i-0009000000-86528933f1fb5f6f49bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 20V, Negative-QTOF	splash10-0a4i-0009000000-779d95151f886854293c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 40V, Negative-QTOF	splash10-01oy-2195000000-06c67f7a540f7657254d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 10V, Positive-QTOF	splash10-0a4i-0009000000-9216d00d19e0b6ee7720	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 20V, Positive-QTOF	splash10-0a4i-0009000000-e8d30684b099443b2b9d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 40V, Positive-QTOF	splash10-014u-0369000000-064772e20e1e0bcdf3cc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 10V, Negative-QTOF	splash10-0a4i-0009000000-c2a6e417d0c66429ddb2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gardenin B 20V, Negative-QTOF	splash10-0btc-0009000000-3fa5c4168345d9b2222f	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

96539

PDB ID

Not Available

ChEBI ID

79628

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1822891

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Gardenin B (HMDB0302154)

MOL for HMDB0302154 (Gardenin B)

3D MOL for HMDB0302154 (Gardenin B)

3D SDF for HMDB0302154 (Gardenin B)

3D-SDF for HMDB0302154 (Gardenin B)

PDB for HMDB0302154 (Gardenin B)

3D PDB for HMDB0302154 (Gardenin B)

SMILES for HMDB0302154 (Gardenin B)

INCHI for HMDB0302154 (Gardenin B)

Structure for HMDB0302154 (Gardenin B)

3D Structure for HMDB0302154 (Gardenin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra