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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:04:06 UTC

Update Date

2022-03-07 02:57:00 UTC

HMDB ID

HMDB0041386

Secondary Accession Numbers

HMDB41386

Metabolite Identification

Common Name

Gancaonin X

Description

Gancaonin X belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Gancaonin X has been detected, but not quantified in, herbs and spices. This could make gancaonin X a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Gancaonin X.

Structure

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

HMDB0041386
     RDKit          3D
Gancaonin X
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.2303    1.4364   -1.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7959    0.0959   -1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735   -0.1186   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768    0.8953   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462    0.6621    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942   -0.6176    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.8662    1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393    0.3153    1.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4385    1.1904    1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    0.6494    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9362    1.2150    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319    0.6243    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803   -0.5675   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5455   -1.1621   -0.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -0.5380    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -1.1657    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277   -1.2283   -1.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0964   -0.6594   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3889    0.5983   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9471    1.5918   -1.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4662    0.3287    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    1.1786    0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -1.6615    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641   -3.0079    0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815   -1.3923   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4600    1.9823   -2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2235    1.5040   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2477    1.9275   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1637    1.9087   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006    1.5470    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -1.7390    1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -0.0631    2.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851    0.8998    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    2.1558    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -2.1083   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -0.8976   -0.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -2.2783   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7470   -2.1847   -1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9194   -1.1719   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6547    1.2976   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5445    2.6033   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0429    1.6529   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3535   -0.0845    0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6705    1.2501    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0085   -0.4303    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426   -3.3419    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549   -2.2260   -0.8903 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  6 23  1  0
 23 24  1  0
 23 25  2  0
 25  3  1  0
 16  7  1  0
 15 10  1  0
 22 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 24 46  1  0
 25 47  1  0
M  END


  Mrv0541 05061312382D          

 25 28  0  0  0  0            999 V2000
    0.6165   -2.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   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
    2.8579   -2.4750    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
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   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
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  4  1  0  0  0  0
 16 10  2  0  0  0  0
 17  5  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  2  0  0  0  0
 19 11  2  0  0  0  0
 19 14  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21  7  1  0  0  0  0
 22 18  1  0  0  0  0
 23  3  1  0  0  0  0
 23 16  1  0  0  0  0
 24 12  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041386

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C(C=C1)C1COC2=CC3=C(C=CC(C)(C)O3)C=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O4/c1-21(2)7-6-13-8-14-9-15(12-24-19(14)11-20(13)25-21)17-5-4-16(23-3)10-18(17)22/h4-8,10-11,15,22H,9,12H2,1-3H3

> <INCHI_KEY>
DRIPWQOGMJYOPU-UHFFFAOYSA-N

> <FORMULA>
C21H22O4

> <MOLECULAR_WEIGHT>
338.397

> <EXACT_MASS>
338.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.252557948718014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-6-yl}-5-methoxyphenol

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
4.238195335333333

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.780430577802923

> <JCHEM_PKA_STRONGEST_BASIC>
-4.385132223319883

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
97.8359

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-6-yl}-5-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041386
     RDKit          3D
Gancaonin X
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.2303    1.4364   -1.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7959    0.0959   -1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735   -0.1186   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768    0.8953   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462    0.6621    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942   -0.6176    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.8662    1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393    0.3153    1.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4385    1.1904    1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    0.6494    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9362    1.2150    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319    0.6243    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803   -0.5675   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5455   -1.1621   -0.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -0.5380    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -1.1657    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277   -1.2283   -1.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0964   -0.6594   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3889    0.5983   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9471    1.5918   -1.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4662    0.3287    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    1.1786    0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -1.6615    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641   -3.0079    0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815   -1.3923   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4600    1.9823   -2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2235    1.5040   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2477    1.9275   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1637    1.9087   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006    1.5470    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -1.7390    1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -0.0631    2.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851    0.8998    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    2.1558    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -2.1083   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -0.8976   -0.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -2.2783   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7470   -2.1847   -1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9194   -1.1719   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6547    1.2976   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5445    2.6033   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0429    1.6529   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3535   -0.0845    0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6705    1.2501    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0085   -0.4303    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426   -3.3419    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549   -2.2260   -0.8903 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  6 23  1  0
 23 24  1  0
 23 25  2  0
 25  3  1  0
 16  7  1  0
 15 10  1  0
 22 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 24 46  1  0
 25 47  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.151  -4.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.141  -6.067   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      16.004   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   23                                                            
CONECT    4    5   16                                                       
CONECT    5    4   17                                                       
CONECT    6    7   13                                                       
CONECT    7    6   21                                                       
CONECT    8   13   14                                                       
CONECT    9   14   15                                                       
CONECT   10   16   18                                                       
CONECT   11   19   20                                                       
CONECT   12   15   24                                                       
CONECT   13    6    8   20                                                  
CONECT   14    8    9   19                                                  
CONECT   15    9   12   17                                                  
CONECT   16    4   10   23                                                  
CONECT   17    5   15   18                                                  
CONECT   18   10   17   22                                                  
CONECT   19   11   14   24                                                  
CONECT   20   11   13   25                                                  
CONECT   21    1    2    7   25                                             
CONECT   22   18                                                            
CONECT   23    3   16                                                       
CONECT   24   12   19                                                       
CONECT   25   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0041386
HETATM    1  C1  UNL     1       7.230   1.436  -1.461  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.796   0.096  -1.327  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.574  -0.119  -0.705  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.777   0.895  -0.221  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.546   0.662   0.403  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.094  -0.618   0.552  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.757  -0.866   1.179  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.339   0.315   1.990  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.438   1.190   1.346  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.697   0.649   0.728  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.936   1.215   0.740  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.032   0.624   0.106  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.780  -0.567  -0.531  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.546  -1.162  -0.562  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.485  -0.538   0.082  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.826  -1.166   0.037  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.928  -1.228  -1.195  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.096  -0.659  -1.141  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.389   0.598  -0.470  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.947   1.592  -1.497  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.466   0.329   0.595  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.274   1.179   0.109  1.00  0.00           O  
HETATM   23  C20 UNL     1       3.855  -1.661   0.086  1.00  0.00           C  
HETATM   24  O4  UNL     1       3.464  -3.008   0.204  1.00  0.00           O  
HETATM   25  C21 UNL     1       5.082  -1.392  -0.535  1.00  0.00           C  
HETATM   26  H1  UNL     1       6.460   1.982  -2.043  1.00  0.00           H  
HETATM   27  H2  UNL     1       8.224   1.504  -1.950  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.248   1.928  -0.448  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.164   1.909  -0.354  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.001   1.547   0.735  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.881  -1.739   1.853  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.794  -0.063   2.914  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.185   0.900   2.380  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.080   2.156   1.257  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.422  -2.108  -1.090  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.298  -0.898  -0.956  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.691  -2.278  -0.042  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.747  -2.185  -1.713  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.919  -1.172  -1.639  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.655   1.298  -2.510  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.544   2.603  -1.303  1.00  0.00           H  
HETATM   42  H17 UNL     1      -7.043   1.653  -1.383  1.00  0.00           H  
HETATM   43  H18 UNL     1      -7.354  -0.085   0.102  1.00  0.00           H  
HETATM   44  H19 UNL     1      -6.671   1.250   1.170  1.00  0.00           H  
HETATM   45  H20 UNL     1      -6.009  -0.430   1.275  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.643  -3.342   0.632  1.00  0.00           H  
HETATM   47  H22 UNL     1       5.655  -2.226  -0.890  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   23
CONECT    7    8   16   31
CONECT    8    9   32   33
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   34
CONECT   12   13   13   22
CONECT   13   14   17
CONECT   14   15   15   35
CONECT   15   16
CONECT   16   36   37
CONECT   17   18   18   38
CONECT   18   19   39
CONECT   19   20   21   22
CONECT   20   40   41   42
CONECT   21   43   44   45
CONECT   23   24   25   25
CONECT   24   46
CONECT   25   47
END

HMDB0041386
     RDKit          3D
Gancaonin X
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.2303    1.4364   -1.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7959    0.0959   -1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735   -0.1186   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768    0.8953   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462    0.6621    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942   -0.6176    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.8662    1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393    0.3153    1.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4385    1.1904    1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    0.6494    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9362    1.2150    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319    0.6243    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803   -0.5675   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5455   -1.1621   -0.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -0.5380    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -1.1657    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277   -1.2283   -1.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0964   -0.6594   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3889    0.5983   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9471    1.5918   -1.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4662    0.3287    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    1.1786    0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -1.6615    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641   -3.0079    0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815   -1.3923   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4600    1.9823   -2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2235    1.5040   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2477    1.9275   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1637    1.9087   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006    1.5470    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -1.7390    1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -0.0631    2.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851    0.8998    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    2.1558    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -2.1083   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -0.8976   -0.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -2.2783   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7470   -2.1847   -1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9194   -1.1719   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6547    1.2976   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5445    2.6033   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0429    1.6529   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3535   -0.0845    0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6705    1.2501    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0085   -0.4303    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426   -3.3419    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549   -2.2260   -0.8903 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  6 23  1  0
 23 24  1  0
 23 25  2  0
 25  3  1  0
 16  7  1  0
 15 10  1  0
 22 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 24 46  1  0
 25 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2'-Hydroxy-4'-methoxy-6'',6''-dimethylpyrano[2'',3'':7,6]isoflavan	HMDB

Chemical Formula

C₂₁H₂₂O₄

Average Molecular Weight

338.397

Monoisotopic Molecular Weight

338.151809192

IUPAC Name

2-{13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-6-yl}-5-methoxyphenol

Traditional Name

2-{13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-6-yl}-5-methoxyphenol

CAS Registry Number

160825-65-0

SMILES

COC1=CC(O)=C(C=C1)C1COC2=CC3=C(C=CC(C)(C)O3)C=C2C1

InChI Identifier

InChI=1S/C21H22O4/c1-21(2)7-6-13-8-14-9-15(12-24-19(14)11-20(13)25-21)17-5-4-16(23-3)10-18(17)22/h4-8,10-11,15,22H,9,12H2,1-3H3

InChI Key

DRIPWQOGMJYOPU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
Isoflavanol
Hydroxyisoflavonoid
Isoflavan
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041386)

Cellular substructure

Membrane (HMDB: HMDB0041386)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041386)

Source

Exogenous

Food

Food (HMDB: HMDB0041386)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041386)

Not Available

Nutrient (HMDB: HMDB0041386)

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	0.25 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	4.37	ALOGPS
logP	4.24	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.84 m³·mol⁻¹	ChemAxon
Polarizability	38.25 Å³	ChemAxon
Number of Rings	4	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
DarkChem	[M+H]+	180.163	31661259
DarkChem	[M-H]-	180.431	31661259
DeepCCS	[M+H]+	184.968	30932474
DeepCCS	[M-H]-	182.61	30932474
DeepCCS	[M-2H]-	216.628	30932474
DeepCCS	[M+Na]+	191.855	30932474
AllCCS	[M+H]+	184.0	32859911
AllCCS	[M+H-H2O]+	180.7	32859911
AllCCS	[M+NH4]+	187.1	32859911
AllCCS	[M+Na]+	188.0	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	187.5	32859911
AllCCS	[M+HCOO]-	187.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gancaonin X	COC1=CC(O)=C(C=C1)C1COC2=CC3=C(C=CC(C)(C)O3)C=C2C1	4020.2	Standard polar	33892256
Gancaonin X	COC1=CC(O)=C(C=C1)C1COC2=CC3=C(C=CC(C)(C)O3)C=C2C1	2763.2	Standard non polar	33892256
Gancaonin X	COC1=CC(O)=C(C=C1)C1COC2=CC3=C(C=CC(C)(C)O3)C=C2C1	3123.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gancaonin X,1TMS,isomer #1	COC1=CC=C(C2COC3=CC4=C(C=CC(C)(C)O4)C=C3C2)C(O[Si](C)(C)C)=C1	2830.1	Semi standard non polar	33892256
Gancaonin X,1TBDMS,isomer #1	COC1=CC=C(C2COC3=CC4=C(C=CC(C)(C)O4)C=C3C2)C(O[Si](C)(C)C(C)(C)C)=C1	3087.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gancaonin X GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-0829000000-d3173579f446dfe34694	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gancaonin X GC-MS (1 TMS) - 70eV, Positive	splash10-0002-2229000000-799fcb3781119f5e550e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gancaonin X GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 10V, Positive-QTOF	splash10-000i-0905000000-59f4e27922dcac82d8ff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 20V, Positive-QTOF	splash10-000i-1922000000-a77218e21fb2f2c17374	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 40V, Positive-QTOF	splash10-0ap1-3910000000-767d7e825fceccfd0185	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 10V, Negative-QTOF	splash10-000i-0209000000-19c99dc2898ae293208a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 20V, Negative-QTOF	splash10-00ri-0669000000-7e5b528578a79795e801	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 40V, Negative-QTOF	splash10-007c-1970000000-baac49db124b821b20d0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 10V, Positive-QTOF	splash10-00kr-0579000000-7371d4fd5fc67983a0f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 20V, Positive-QTOF	splash10-0079-2459000000-147b02a9fe4d479daa83	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 40V, Positive-QTOF	splash10-0kg9-2975000000-7dc81d6340af6b6b6fe8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 10V, Negative-QTOF	splash10-000i-0019000000-1793f04ff65872058920	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 20V, Negative-QTOF	splash10-000i-0149000000-15fc94dc8688f6c43604	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gancaonin X 40V, Negative-QTOF	splash10-0zid-1192000000-32f930e30f1e3ab7bd1e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB021318

KNApSAcK ID

C00019338

Chemspider ID

35015170

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101666683

PDB ID

Not Available

ChEBI ID

174551

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1891971

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Gancaonin X (HMDB0041386)

MOL for HMDB0041386 (Gancaonin X)

3D MOL for HMDB0041386 (Gancaonin X)

3D SDF for HMDB0041386 (Gancaonin X)

3D-SDF for HMDB0041386 (Gancaonin X)

PDB for HMDB0041386 (Gancaonin X)

3D PDB for HMDB0041386 (Gancaonin X)

SMILES for HMDB0041386 (Gancaonin X)

INCHI for HMDB0041386 (Gancaonin X)

Structure for HMDB0041386 (Gancaonin X)

3D Structure for HMDB0041386 (Gancaonin X)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra