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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:35:27 UTC

Update Date

2022-03-07 02:53:52 UTC

HMDB ID

HMDB0033817

Secondary Accession Numbers

HMDB33817

Metabolite Identification

Common Name

4-Hydroxy-2,3,9-trimethoxypterocarpan

Description

4-Hydroxy-2,3,9-trimethoxypterocarpan belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 4-hydroxy-2,3,9-trimethoxypterocarpan is considered to be a flavonoid. 4-Hydroxy-2,3,9-trimethoxypterocarpan has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make 4-hydroxy-2,3,9-trimethoxypterocarpan a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Hydroxy-2,3,9-trimethoxypterocarpan.

Structure

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

HMDB0033817
     RDKit          3D
4-Hydroxy-2,3,9-trimethoxypterocarpan
 42 45  0  0  0  0  0  0  0  0999 V2000
    7.0373    0.6108   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7446    0.9599   -1.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    0.5482   -0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.1857    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.5880    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.2572    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381    0.4707   -0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    0.8566   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8454    0.6569   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2082   -0.4451   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1980   -0.1918    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -0.3320   -0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243   -0.1090   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4965   -0.2615   -1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643   -0.6514   -2.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9150    0.2734    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419    0.4992    0.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1603   -0.4533    1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9528    0.4201    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3058    0.7992    2.9813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5985    0.1859    1.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    0.3361    2.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717    0.6449    1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771   -0.5214    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7304    0.7899   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375    1.1370   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0851   -0.4779   -1.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7914   -0.4334    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.1577    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2259    1.4238   -2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -1.3684   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -0.6297   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376    0.0125   -3.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9201   -0.4742   -3.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6923   -1.6827   -2.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4980   -0.2652    2.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8182   -1.4874    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1009   -0.3759    0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.9105    3.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246    1.5517    1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.7451    2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216   -1.4832    1.5965 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 24 10  1  0
 24  6  1  0
 21 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
M  END

  Mrv0541 05061307232D          

 24 27  0  0  0  0            999 V2000
    7.2186    1.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    0.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521    1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289    1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762    1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    1.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    3.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  2  0  0  0  0
 14  7  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 21  2  1  0  0  0  0
 21 14  1  0  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
 24 13  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033817

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-20-9-4-5-10-12-8-23-17-11(16(12)24-13(10)6-9)7-14(21-2)18(22-3)15(17)19/h4-7,12,16,19H,8H2,1-3H3

> <INCHI_KEY>
APDOGYRSSCEXNB-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.328817491213584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-6-ol

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.1938808649999997

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.170456613586337

> <JCHEM_PKA_STRONGEST_BASIC>
-4.20409641636387

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
85.9875

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033817
     RDKit          3D
4-Hydroxy-2,3,9-trimethoxypterocarpan
 42 45  0  0  0  0  0  0  0  0999 V2000
    7.0373    0.6108   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7446    0.9599   -1.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    0.5482   -0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.1857    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.5880    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.2572    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381    0.4707   -0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    0.8566   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8454    0.6569   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2082   -0.4451   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1980   -0.1918    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -0.3320   -0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243   -0.1090   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4965   -0.2615   -1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643   -0.6514   -2.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9150    0.2734    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419    0.4992    0.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1603   -0.4533    1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9528    0.4201    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3058    0.7992    2.9813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5985    0.1859    1.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    0.3361    2.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717    0.6449    1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771   -0.5214    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7304    0.7899   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375    1.1370   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0851   -0.4779   -1.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7914   -0.4334    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.1577    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2259    1.4238   -2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -1.3684   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -0.6297   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376    0.0125   -3.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9201   -0.4742   -3.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6923   -1.6827   -2.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4980   -0.2652    2.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8182   -1.4874    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1009   -0.3759    0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.9105    3.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246    1.5517    1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.7451    2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216   -1.4832    1.5965 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 24 10  1  0
 24  6  1  0
 21 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  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      13.475   3.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.560   5.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.100   1.528   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.975   1.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.742   3.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.512   1.793   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.282   0.329   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.179   4.492   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.977   5.655   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.408   2.904   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    9   13                                                       
CONECT    7   11   14                                                       
CONECT    8   12   23                                                       
CONECT    9    4    6   20                                                  
CONECT   10    5   12   13                                                  
CONECT   11    7   16   17                                                  
CONECT   12    8   10   16                                                  
CONECT   13    6   10   24                                                  
CONECT   14    7   18   21                                                  
CONECT   15   17   18   19                                                  
CONECT   16   11   12   24                                                  
CONECT   17   11   15   23                                                  
CONECT   18   14   15   22                                                  
CONECT   19   15                                                            
CONECT   20    1    9                                                       
CONECT   21    2   14                                                       
CONECT   22    3   18                                                       
CONECT   23    8   17                                                       
CONECT   24   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0033817
HETATM    1  C1  UNL     1       7.037   0.611  -1.287  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.745   0.960  -1.736  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.635   0.548  -0.976  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.794  -0.186   0.191  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.706  -0.588   0.934  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.434  -0.257   0.513  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.238   0.471  -0.642  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.349   0.857  -1.360  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.845   0.657  -0.823  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.208  -0.445  -0.154  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.198  -0.192   0.170  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.188  -0.332  -0.795  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.524  -0.109  -0.542  1.00  0.00           C  
HETATM   14  O3  UNL     1      -4.497  -0.262  -1.546  1.00  0.00           O  
HETATM   15  C12 UNL     1      -4.064  -0.651  -2.827  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.915   0.273   0.729  1.00  0.00           C  
HETATM   17  O4  UNL     1      -5.242   0.499   0.997  1.00  0.00           O  
HETATM   18  C14 UNL     1      -6.160  -0.453   1.445  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.953   0.420   1.706  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.306   0.799   2.981  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.599   0.186   1.418  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.641   0.336   2.406  1.00  0.00           O  
HETATM   23  C17 UNL     1       0.672   0.645   1.987  1.00  0.00           C  
HETATM   24  C18 UNL     1       1.077  -0.521   1.075  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.730   0.790  -2.133  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.338   1.137  -0.365  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.085  -0.478  -1.076  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.791  -0.433   0.502  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.818  -1.158   1.841  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.226   1.424  -2.262  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.313  -1.368  -0.775  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.896  -0.630  -1.790  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.238   0.012  -3.207  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.920  -0.474  -3.541  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.692  -1.683  -2.881  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.498  -0.265   2.496  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.818  -1.487   1.406  1.00  0.00           H  
HETATM   38  H14 UNL     1      -7.101  -0.376   0.833  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.613   0.911   3.706  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.625   1.552   1.357  1.00  0.00           H  
HETATM   41  H17 UNL     1       1.376   0.745   2.834  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.022  -1.483   1.596  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   24
CONECT    7    8    8    9
CONECT    8   30
CONECT    9   10
CONECT   10   11   24   31
CONECT   11   12   12   21
CONECT   12   13   32
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   33   34   35
CONECT   16   17   19
CONECT   17   18
CONECT   18   36   37   38
CONECT   19   20   21   21
CONECT   20   39
CONECT   21   22
CONECT   22   23
CONECT   23   24   40   41
CONECT   24   42
END

HMDB0033817
     RDKit          3D
4-Hydroxy-2,3,9-trimethoxypterocarpan
 42 45  0  0  0  0  0  0  0  0999 V2000
    7.0373    0.6108   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7446    0.9599   -1.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    0.5482   -0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.1857    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.5880    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.2572    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381    0.4707   -0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    0.8566   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8454    0.6569   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2082   -0.4451   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1980   -0.1918    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -0.3320   -0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243   -0.1090   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4965   -0.2615   -1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643   -0.6514   -2.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9150    0.2734    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419    0.4992    0.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1603   -0.4533    1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9528    0.4201    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3058    0.7992    2.9813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5985    0.1859    1.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    0.3361    2.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717    0.6449    1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771   -0.5214    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7304    0.7899   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375    1.1370   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0851   -0.4779   -1.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7914   -0.4334    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.1577    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2259    1.4238   -2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -1.3684   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -0.6297   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376    0.0125   -3.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9201   -0.4742   -3.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6923   -1.6827   -2.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4980   -0.2652    2.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8182   -1.4874    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1009   -0.3759    0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.9105    3.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246    1.5517    1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.7451    2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216   -1.4832    1.5965 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 24 10  1  0
 24  6  1  0
 21 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6a,11a-dihydro-2,3,9-Trimethoxy-6H-benzofuro[3,2-c][1]benzopyran-4-ol, 9ci	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Molecular Weight

330.3319

Monoisotopic Molecular Weight

330.110338308

IUPAC Name

4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-6-ol

Traditional Name

4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-6-ol

CAS Registry Number

56841-82-8

SMILES

COC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O2

InChI Identifier

InChI=1S/C18H18O6/c1-20-9-4-5-10-12-8-23-17-11(16(12)24-13(10)6-9)7-14(21-2)18(22-3)15(17)19/h4-7,12,16,19H,8H2,1-3H3

InChI Key

APDOGYRSSCEXNB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070089 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033817)
Cell membrane (HMDB: HMDB0033817)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033817)

Source

Exogenous

Exogenous (HMDB: HMDB0033817)

Food

Food (HMDB: HMDB0033817)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033817)
Fabaceae (HMDB: HMDB0033817)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033817)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 - 145 °C	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
Water Solubility	0.099 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.99 m³·mol⁻¹	ChemAxon
Polarizability	34.33 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]+	178.246	31661259
DarkChem	[M-H]-	178.13	31661259
DeepCCS	[M+H]+	177.749	30932474
DeepCCS	[M-H]-	175.391	30932474
DeepCCS	[M-2H]-	209.463	30932474
DeepCCS	[M+Na]+	184.69	30932474
AllCCS	[M+H]+	177.8	32859911
AllCCS	[M+H-H2O]+	174.5	32859911
AllCCS	[M+NH4]+	180.9	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	182.4	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	181.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2,3,9-trimethoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O2	4068.5	Standard polar	33892256
4-Hydroxy-2,3,9-trimethoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O2	2670.3	Standard non polar	33892256
4-Hydroxy-2,3,9-trimethoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O2	2827.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-2,3,9-trimethoxypterocarpan,1TMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC(OC)=C(OC)C(O[Si](C)(C)C)=C3OCC21	2822.6	Semi standard non polar	33892256
4-Hydroxy-2,3,9-trimethoxypterocarpan,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC(OC)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	3058.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gba-0739000000-1612946b221d02cc0048	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan GC-MS (1 TMS) - 70eV, Positive	splash10-0079-1129000000-50a1ad62992542def8ab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 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 - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Positive-QTOF	splash10-00lr-0509000000-1fb33ec9c409a691f00a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Positive-QTOF	splash10-00lr-0629000000-0ff70174fb6e16fab96c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Positive-QTOF	splash10-03y1-2910000000-f098e6385ff8e7a72570	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Negative-QTOF	splash10-004i-0009000000-38d5cd86001d90f602bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Negative-QTOF	splash10-01ta-0069000000-9f5a67b20b156424917c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Negative-QTOF	splash10-06wc-2390000000-dfbed0c21ebeb62a9062	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Positive-QTOF	splash10-001i-0009000000-2160799bc7c624fd0646	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Positive-QTOF	splash10-001i-0009000000-b00061307acdcb1e67c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Positive-QTOF	splash10-03xr-0693000000-208fd85a933bc5628f9d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Negative-QTOF	splash10-004i-0009000000-de11969ae6615b28f3d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Negative-QTOF	splash10-016s-0094000000-4d8d06564b41844767d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Negative-QTOF	splash10-05mx-2191000000-b9eda0f9598c4758bd08	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

FDB011981

KNApSAcK ID

C00009633

Chemspider ID

24843022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23036629

PDB ID

Not Available

ChEBI ID

Not Available

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

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

Showing metabocard for 4-Hydroxy-2,3,9-trimethoxypterocarpan (HMDB0033817)

MOL for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D MOL for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D SDF for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D-SDF for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

PDB for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D PDB for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

SMILES for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

INCHI for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

Structure for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D Structure for HMDB0033817 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra