NP-MRD: Showing NP-Card for (2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid (NP0215064)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 14:32:10 UTC

Updated at

2022-09-05 14:32:10 UTC

NP-MRD ID

NP0215064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid

Description

Torvanol A belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Torvanol A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Torvanol A has been detected, but not quantified in, fruits. (2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid is found in Solanum torvum. This could make torvanol a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310392D          

 31 33  0  0  0  0            999 V2000
   -0.7145    2.0625    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
    5.0013    4.5375    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    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
    1.7309    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  2  0  0  0  0
 18  6  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 18  2  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 27  1  1  0  0  0  0
 27 12  1  0  0  0  0
 28  2  1  0  0  0  0
 28 17  1  0  0  0  0
 29 10  1  0  0  0  0
 29 16  1  0  0  0  0
 30 20  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  2  0  0  0  0
 31 26  2  0  0  0  0
 31 30  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -5.8978    3.2335   -1.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8629    2.3297   -1.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2276    1.5759   -0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6238    1.7019    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407    0.9811    1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253    0.1204    1.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340   -0.0052   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922    0.6826   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4933   -1.0294   -0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0929   -2.1765    0.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6447   -3.2628   -0.9062 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.3801   -2.6319   -2.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087   -4.1811   -1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7569   -4.2599   -0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.5186    0.5496 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9606   -0.6040    0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680    0.5296    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1208    0.5657    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8478    1.8653    0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    1.9991   -0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8391    3.2147   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9601    3.1978   -0.7615 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4427    4.4199    0.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7003   -0.5544   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632   -1.7190   -0.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5836   -2.8416   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9558   -2.8564   -1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150   -1.6944   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8269   -2.8205   -0.3920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442   -0.4791    2.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3034   -0.6623    2.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4651    3.8756   -0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1505    3.8528   -2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8150    2.7393   -1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4117    2.3724    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3608    1.0861    2.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676    0.5633   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815   -1.1288   -1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -4.6309    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850    0.6990    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    1.4549    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4358    2.7025    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455    1.1307   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4906    5.2208   -0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7683   -0.5981   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4994   -2.9467   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -1.9710   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1874   -3.7961   -1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1768   -3.6729   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5014    0.3709    2.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4454   -1.4438    2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  7  1  0
  7  6  2  0
  6 31  1  0
 31 30  1  0
 30 15  1  0
 15  9  1  0
  9 10  1  0
 10 11  1  0
 11 14  1  0
 11 12  2  0
 11 13  2  0
 15 16  1  0
 16 28  2  0
 28 29  1  0
 28 25  1  0
 25 26  1  0
 26 27  1  0
 25 24  2  0
 24 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
 18 17  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  9  7  1  0
 17 16  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  8 37  1  0
 30 50  1  0
 30 51  1  0
 15 40  1  6
  9 38  1  6
 14 39  1  0
 29 49  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 24 45  1  0
 19 42  1  0
 20 43  1  0
 23 44  1  0
 17 41  1  0
  5 36  1  0
  4 35  1  0
M  END


  Mrv0541 05061310392D          

 31 33  0  0  0  0            999 V2000
   -0.7145    2.0625    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
    5.0013    4.5375    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    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
    1.7309    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  2  0  0  0  0
 18  6  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 18  2  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 27  1  1  0  0  0  0
 27 12  1  0  0  0  0
 28  2  1  0  0  0  0
 28 17  1  0  0  0  0
 29 10  1  0  0  0  0
 29 16  1  0  0  0  0
 30 20  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  2  0  0  0  0
 31 26  2  0  0  0  0
 31 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(OCC(C2OS(O)(=O)=O)C2=C(O)C(OC)=CC(\C=C\C(O)=O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O10S/c1-27-12-4-5-16-14(9-12)20(30-31(24,25)26)15(10-29-16)13-7-11(3-6-18(21)22)8-17(28-2)19(13)23/h3-9,15,20,23H,10H2,1-2H3,(H,21,22)(H,24,25,26)/b6-3+

> <INCHI_KEY>
XKGLTSPFQHSIDD-ZZXKWVIFSA-N

> <FORMULA>
C20H20O10S

> <MOLECULAR_WEIGHT>
452.432

> <EXACT_MASS>
452.07771755

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
43.43941070628324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acid

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
2.208472539666666

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.3208566700699635

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.893714457863637

> <JCHEM_PKA_STRONGEST_BASIC>
-4.376171689138406

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
108.31609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   3.850   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  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.231   5.596   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.771   8.264   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   31  S   UNK     0       4.001   6.930   0.000  0.00  0.00           S+0
CONECT    1   27                                                            
CONECT    2   28                                                            
CONECT    3    6   11                                                       
CONECT    4    5   12                                                       
CONECT    5    4   16                                                       
CONECT    6    3   18                                                       
CONECT    7   11   13                                                       
CONECT    8   11   17                                                       
CONECT    9   12   14                                                       
CONECT   10   15   29                                                       
CONECT   11    3    7    8                                                  
CONECT   12    4    9   27                                                  
CONECT   13    7   15   19                                                  
CONECT   14    9   16   20                                                  
CONECT   15   10   13   20                                                  
CONECT   16    5   14   29                                                  
CONECT   17    8   19   28                                                  
CONECT   18    6   21   22                                                  
CONECT   19   13   17   23                                                  
CONECT   20   14   15   30                                                  
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   31                                                            
CONECT   25   31                                                            
CONECT   26   31                                                            
CONECT   27    1   12                                                       
CONECT   28    2   17                                                       
CONECT   29   10   16                                                       
CONECT   30   20   31                                                       
CONECT   31   24   25   26   30                                             
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
4-Sulfate-2'-hydroxy-6,3'-dimethoxy-5'-(2-propenoic acid)isoflavone	HMDB
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoate	Generator
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulphooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoate	Generator
(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulphooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acid	Generator
Torvanol a	MeSH

Chemical Formula

C₂₀H₂₀O₁₀S

Average Mass

452.4320 Da

Monoisotopic Mass

452.07772 Da

IUPAC Name

(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acid

Traditional Name

(2E)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-3-yl]phenyl}prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(OCC(C2OS(O)(=O)=O)C2=C(O)C(OC)=CC(\C=C\C(O)=O)=C2)C=C1

InChI Identifier

InChI=1S/C20H20O10S/c1-27-12-4-5-16-14(9-12)20(30-31(24,25)26)15(10-29-16)13-7-11(3-6-18(21)22)8-17(28-2)19(13)23/h3-9,15,20,23H,10H2,1-2H3,(H,21,22)(H,24,25,26)/b6-3+

InChI Key

XKGLTSPFQHSIDD-ZZXKWVIFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum torvum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C6 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

6-O-methylated isoflavonoids

Alternative Parents

Substituents

3p-methoxyisoflavonoid-skeleton
6-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Methoxyphenol
1-benzopyran
Benzopyran
Chromane
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Phenol
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Benzenoid
Sulfuric acid monoester
Monocyclic benzene moiety
Organic sulfuric acid or derivatives
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Ether
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.71	ALOGPS
logP	2.21	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.32 m³·mol⁻¹	ChemAxon
Polarizability	43.44 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0038789

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018213

KNApSAcK ID

C00019212

Chemspider ID

4479588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321987

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid (NP0215064)

MOL for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

3D MOL for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

3D SDF for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

3D-SDF for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

PDB for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

3D PDB for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

SMILES for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

INCHI for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

Structure for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)

3D Structure for NP0215064 ((2e)-3-{4-hydroxy-3-methoxy-5-[6-methoxy-4-(sulfooxy)-3,4-dihydro-2h-1-benzopyran-3-yl]phenyl}prop-2-enoic acid)