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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:45:42 UTC

Update Date

2022-03-07 02:53:56 UTC

HMDB ID

HMDB0033986

Secondary Accession Numbers

HMDB33986

Metabolite Identification

Common Name

Demethylvestitol

Description

Demethylvestitol, also known as pipecurium or arduan, belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Thus, demethylvestitol is considered to be a flavonoid. Demethylvestitol has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), green beans (Phaseolus vulgaris), pulses, scarlet beans (Phaseolus coccineus), and yellow wax beans (Phaseolus vulgaris). This could make demethylvestitol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Demethylvestitol.

Structure

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

HMDB0033986
     RDKit          3D
Demethylvestitol
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.4556    0.7941   -1.2382 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1994    0.5269   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049    1.5007   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    1.1552    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175   -0.1396    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3781   -0.4967    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    0.7246    1.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    1.4587    0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.7597    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3546    1.2841    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3616    0.5381   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6082    1.0903   -0.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1257   -0.7610   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -1.2989   -0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8444   -0.5357   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116   -1.1277    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -1.1055    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -2.4382    0.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -0.7829   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2694    0.9626   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5605    2.5304   -0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761    1.9531    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -1.2719    1.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5884    1.3639    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087    0.3798    2.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    2.3231    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8715    2.0245   -0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9085   -1.3947   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6530   -2.3311   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6951   -2.2333    0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377   -1.1469   -0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946   -2.7385    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661   -1.5673   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
 16  6  1  0
 15  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv0541 05061307292D          

 19 21  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  2  0  0  0  0
 12  2  1  0  0  0  0
 12  7  2  0  0  0  0
 13  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  2  0  0  0  0
 15  7  1  0  0  0  0
 15  9  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033986

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c16-11-3-4-13(14(18)6-11)10-5-9-1-2-12(17)7-15(9)19-8-10/h1-4,6-7,10,16-18H,5,8H2

> <INCHI_KEY>
CJZBXHPHEBCWLV-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.15727209159045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)benzene-1,3-diol

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.888112555666666

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.937816580595957

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.328246630474686

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855579298160206

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
70.94110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demethylvestitol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033986
     RDKit          3D
Demethylvestitol
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.4556    0.7941   -1.2382 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1994    0.5269   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049    1.5007   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    1.1552    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175   -0.1396    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3781   -0.4967    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    0.7246    1.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    1.4587    0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.7597    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3546    1.2841    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3616    0.5381   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6082    1.0903   -0.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1257   -0.7610   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -1.2989   -0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8444   -0.5357   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116   -1.1277    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -1.1055    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -2.4382    0.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -0.7829   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2694    0.9626   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5605    2.5304   -0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761    1.9531    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -1.2719    1.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5884    1.3639    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087    0.3798    2.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    2.3231    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8715    2.0245   -0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9085   -1.3947   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6530   -2.3311   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6951   -2.2333    0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377   -1.1469   -0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946   -2.7385    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661   -1.5673   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
 16  6  1  0
 15  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   12                                                       
CONECT    3    4   11                                                       
CONECT    4    3   13                                                       
CONECT    5    9   10                                                       
CONECT    6   11   14                                                       
CONECT    7   12   15                                                       
CONECT    8   10   19                                                       
CONECT    9    1    5   15                                                  
CONECT   10    5    8   13                                                  
CONECT   11    3    6   16                                                  
CONECT   12    2    7   17                                                  
CONECT   13    4   10   14                                                  
CONECT   14    6   13   18                                                  
CONECT   15    7    9   19                                                  
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0033986
HETATM    1  O1  UNL     1       5.456   0.794  -1.238  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.199   0.527  -0.664  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.305   1.501  -0.357  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.082   1.155   0.209  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.718  -0.140   0.484  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.378  -0.497   1.060  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.187   0.725   1.699  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.030   1.459   0.798  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.088   0.760   0.228  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.355   1.284   0.022  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.362   0.538  -0.545  1.00  0.00           C  
HETATM   12  O3  UNL     1      -5.608   1.090  -0.734  1.00  0.00           O  
HETATM   13  C10 UNL     1      -4.126  -0.761  -0.925  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.878  -1.299  -0.730  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.844  -0.536  -0.148  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.512  -1.128   0.046  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.629  -1.106   0.170  1.00  0.00           C  
HETATM   18  O4  UNL     1       2.350  -2.438   0.414  1.00  0.00           O  
HETATM   19  C15 UNL     1       3.878  -0.783  -0.407  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.269   0.963  -0.649  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.560   2.530  -0.561  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.376   1.953   0.437  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.543  -1.272   1.868  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.588   1.364   2.113  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.809   0.380   2.571  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.504   2.323   0.336  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.871   2.025  -0.487  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.908  -1.395  -1.384  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.653  -2.331  -1.020  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.695  -2.233   0.239  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.038  -1.147  -0.947  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.495  -2.738   0.836  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.566  -1.567  -0.639  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3    3   19
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   17
CONECT    6    7   16   23
CONECT    7    8   24   25
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   26
CONECT   11   12   13   13
CONECT   12   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   30   31
CONECT   17   18   19   19
CONECT   18   32
CONECT   19   33
END

HMDB0033986
     RDKit          3D
Demethylvestitol
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.4556    0.7941   -1.2382 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1994    0.5269   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049    1.5007   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    1.1552    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175   -0.1396    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3781   -0.4967    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    0.7246    1.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    1.4587    0.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.7597    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3546    1.2841    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3616    0.5381   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6082    1.0903   -0.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1257   -0.7610   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -1.2989   -0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8444   -0.5357   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116   -1.1277    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -1.1055    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -2.4382    0.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -0.7829   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2694    0.9626   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5605    2.5304   -0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761    1.9531    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -1.2719    1.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5884    1.3639    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8087    0.3798    2.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    2.3231    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8715    2.0245   -0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9085   -1.3947   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6530   -2.3311   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6951   -2.2333    0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377   -1.1469   -0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946   -2.7385    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661   -1.5673   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
 16  6  1  0
 15  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pipecuronium	MeSH
Pipecuronium dibromide, (17 alpha)-isomer	MeSH
Pipecuronium dibromide, (3 beta)-isomer	MeSH
Pipecuronium dibromide, dihydrate	MeSH
Pipecurium	MeSH
Bromide, pipecurium	MeSH
Bromide, pipecuronium	MeSH
Pipecuronium bromide	MeSH
Pipecuronium dibromide, (16 alpha)-isomer	MeSH
Arduan	MeSH
Dibromide pipecuronium	MeSH
Dibromide, dihydrate pipecuronium	MeSH
Dihydrate pipecuronium dibromide	MeSH
Pipecurium bromide	MeSH
Pipecuronium, dibromide	MeSH
3,4-dihydro-3-(2,4-Dihydroxyphenyl)-7-hydroxy-2H-1-benzopyran	HMDB
4-(3,4-dihydro-7-Hydroxy-2H-1-benzopyran-4-yl)-1,3-benzenediol, 9ci	HMDB
7,2',4'-Trihydroxyisoflavan	HMDB
pipecuronio Bromuro	HMDB

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)benzene-1,3-diol

Traditional Name

demethylvestitol

CAS Registry Number

65332-45-8

SMILES

OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

InChI Identifier

InChI=1S/C15H14O4/c16-11-3-4-13(14(18)6-11)10-5-9-1-2-12(17)7-15(9)19-8-10/h1-4,6-7,10,16-18H,5,8H2

InChI Key

CJZBXHPHEBCWLV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

Alternative Parents

Substituents

Isoflavanol
Hydroxyisoflavonoid
Chromane
Benzopyran
1-benzopyran
Resorcinol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080027 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033986)
Cytoplasm (HMDB: HMDB0033986)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033986)

Source

Exogenous

Exogenous (HMDB: HMDB0033986)

Food

Food (HMDB: HMDB0033986)

Pulse

Bean

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033986)
Fabaceae (HMDB: HMDB0033986)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033986)
Phytoalexin (HMDB: HMDB0033986)

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0033986)

Pesticide (HMDB: HMDB0033986)

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
Water Solubility	0.088 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.89	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.94 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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
DarkChem	[M+H]+	160.87	31661259
DarkChem	[M-H]-	157.907	31661259
DeepCCS	[M+H]+	162.723	30932474
DeepCCS	[M-H]-	160.365	30932474
DeepCCS	[M-2H]-	193.251	30932474
DeepCCS	[M+Na]+	168.816	30932474
AllCCS	[M+H]+	159.9	32859911
AllCCS	[M+H-H2O]+	156.0	32859911
AllCCS	[M+NH4]+	163.6	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	162.4	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	161.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.28 minutes	32390414
Predicted by Siyang on May 30, 2022	11.398 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.7 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1545.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	586.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	414.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	918.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	396.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1221.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	402.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	111.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Demethylvestitol	OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	3515.6	Standard polar	33892256
Demethylvestitol	OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	2691.4	Standard non polar	33892256
Demethylvestitol	OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	2869.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Demethylvestitol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O)=C1	2675.7	Semi standard non polar	33892256
Demethylvestitol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC=C1C1COC2=CC(O)=CC=C2C1	2650.8	Semi standard non polar	33892256
Demethylvestitol,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O)COC2=C1	2669.9	Semi standard non polar	33892256
Demethylvestitol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)C(O)=C1	2660.5	Semi standard non polar	33892256
Demethylvestitol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O[Si](C)(C)C)=C1	2696.9	Semi standard non polar	33892256
Demethylvestitol,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O[Si](C)(C)C)COC2=C1	2684.4	Semi standard non polar	33892256
Demethylvestitol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)COC2=C1	2617.3	Semi standard non polar	33892256
Demethylvestitol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O)=C1	2956.5	Semi standard non polar	33892256
Demethylvestitol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1COC2=CC(O)=CC=C2C1	2945.5	Semi standard non polar	33892256
Demethylvestitol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O)COC2=C1	2960.3	Semi standard non polar	33892256
Demethylvestitol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)C(O)=C1	3187.3	Semi standard non polar	33892256
Demethylvestitol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O[Si](C)(C)C(C)(C)C)=C1	3191.3	Semi standard non polar	33892256
Demethylvestitol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)COC2=C1	3188.2	Semi standard non polar	33892256
Demethylvestitol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)COC2=C1	3261.2	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 - Demethylvestitol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0553-0590000000-2c0bca31092dfea212e7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylvestitol GC-MS (3 TMS) - 70eV, Positive	splash10-0zmi-3022900000-4539bb07bfffda37b174	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylvestitol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylvestitol 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 - Demethylvestitol 10V, Positive-QTOF	splash10-0ab9-0890000000-feebc814b570d1822973	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 20V, Positive-QTOF	splash10-00dl-0950000000-8613c9fd6e87aaa46cfc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 40V, Positive-QTOF	splash10-05fr-3920000000-28cde73d029166d04627	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 10V, Negative-QTOF	splash10-0a4i-0390000000-bc72e3f53044527a2755	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 20V, Negative-QTOF	splash10-0a4i-0980000000-5c07eb85c5df3850f182	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 40V, Negative-QTOF	splash10-0ab9-3910000000-cdd6f51494588e40ce3b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 10V, Positive-QTOF	splash10-0a4j-0590000000-0fc888d544d19b178a04	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 20V, Positive-QTOF	splash10-0a4j-0980000000-ff6cd3ec3ced984c021f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 40V, Positive-QTOF	splash10-00ri-4920000000-88560d7baa6e7c78b330	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 10V, Negative-QTOF	splash10-0a4i-0290000000-31d1297674ece6f611b5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 20V, Negative-QTOF	splash10-0a4i-0690000000-88623afb300c6aaee822	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylvestitol 40V, Negative-QTOF	splash10-01wr-0910000000-e1ac3be06a5cc42b713f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB012218

KNApSAcK ID

C00009708

Chemspider ID

509323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

585939

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Demethylvestitol → 6-{[3-(2,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Demethylvestitol → 3,4,5-trihydroxy-6-[5-hydroxy-2-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]oxane-2-carboxylic acid	details
Demethylvestitol → 3,4,5-trihydroxy-6-[3-hydroxy-4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]oxane-2-carboxylic acid	details

Showing metabocard for Demethylvestitol (HMDB0033986)

MOL for HMDB0033986 (Demethylvestitol)

3D MOL for HMDB0033986 (Demethylvestitol)

3D SDF for HMDB0033986 (Demethylvestitol)

3D-SDF for HMDB0033986 (Demethylvestitol)

PDB for HMDB0033986 (Demethylvestitol)

3D PDB for HMDB0033986 (Demethylvestitol)

SMILES for HMDB0033986 (Demethylvestitol)

INCHI for HMDB0033986 (Demethylvestitol)

Structure for HMDB0033986 (Demethylvestitol)

3D Structure for HMDB0033986 (Demethylvestitol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions