Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:15:00 UTC

Update Date

2022-03-07 02:55:59 UTC

HMDB ID

HMDB0038902

Secondary Accession Numbers

HMDB38902

Metabolite Identification

Common Name

Lupiwighteone

Description

Lupiwighteone belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, lupiwighteone is considered to be a flavonoid. Lupiwighteone has been detected, but not quantified in, a few different foods, such as adzuki beans (Vigna angularis), herbs and spices, and pulses. This could make lupiwighteone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Lupiwighteone.

Structure

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

HMDB0038902
     RDKit          3D
Lupiwighteone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1077    2.7635    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    1.3655    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176    0.3248    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2979    1.1314    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773   -0.1790    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -0.6296   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287   -1.1158   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7297   -1.2089   -1.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5091   -1.4998   -2.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999   -1.4044   -2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6920   -1.8019   -3.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4484   -0.9130   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8021   -0.7816   -0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -1.1283   -1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -0.2754    0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -0.1314    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    0.4170   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8620    0.5280   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4002    0.1315    1.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7751    0.2774    1.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639   -0.4099    2.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2198   -0.5420    1.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    0.0741    1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0587   -0.0638    0.9097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -0.5291   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9848    2.9959    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3735    2.8935   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    3.4500    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5376    0.5916    0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3438   -0.6844    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668    0.3488    1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164    1.9615    0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -0.1088    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3924   -1.0035    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -1.5693   -2.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718   -1.8899   -3.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6297   -1.8373   -3.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140    0.7329   -1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5074    0.9542   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1890   -0.0043    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9194   -0.7390    2.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5695   -0.9686    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929    0.4772    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  2  0
 23 24  1  0
 24 25  1  0
 25  6  1  0
 25 12  2  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
M  END


  Mrv0541 05061310432D          

 25 27  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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    2.0625    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    2.4750    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
    1.4289    0.0000    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
    3.5724    1.2375    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    2.4750    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    0.8250    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
    0.7145    1.2375    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
    2.1434    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16  9  2  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 18 17  2  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21 13  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 19  2  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038902

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17(23)18-19(24)15(10-25-20(14)18)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3

> <INCHI_KEY>
YGCCASGFIOIXIN-UHFFFAOYSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.3539

> <EXACT_MASS>
338.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.126196178628135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
4.805439389

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.783767230306104

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.422282378773507

> <JCHEM_PKA_STRONGEST_BASIC>
-5.1808273876825135

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
95.92569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lupiwighteone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038902
     RDKit          3D
Lupiwighteone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1077    2.7635    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    1.3655    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176    0.3248    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2979    1.1314    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773   -0.1790    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -0.6296   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287   -1.1158   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7297   -1.2089   -1.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5091   -1.4998   -2.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999   -1.4044   -2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6920   -1.8019   -3.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4484   -0.9130   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8021   -0.7816   -0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -1.1283   -1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -0.2754    0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -0.1314    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    0.4170   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8620    0.5280   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4002    0.1315    1.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7751    0.2774    1.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639   -0.4099    2.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2198   -0.5420    1.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    0.0741    1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0587   -0.0638    0.9097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -0.5291   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9848    2.9959    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3735    2.8935   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    3.4500    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5376    0.5916    0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3438   -0.6844    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668    0.3488    1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164    1.9615    0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -0.1088    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3924   -1.0035    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -1.5693   -2.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718   -1.8899   -3.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6297   -1.8373   -3.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140    0.7329   -1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5074    0.9542   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1890   -0.0043    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9194   -0.7390    2.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5695   -0.9686    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929    0.4772    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  2  0
 23 24  1  0
 24 25  1  0
 25  6  1  0
 25 12  2  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  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  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    8   11                                                       
CONECT    4    6   12                                                       
CONECT    5    7   12                                                       
CONECT    6    4   13                                                       
CONECT    7    5   13                                                       
CONECT    8    3   14                                                       
CONECT    9   16   17                                                       
CONECT   10   15   25                                                       
CONECT   11    1    2    3                                                  
CONECT   12    4    5   15                                                  
CONECT   13    6    7   21                                                  
CONECT   14    8   16   20                                                  
CONECT   15   10   12   19                                                  
CONECT   16    9   14   22                                                  
CONECT   17    9   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   15   18   24                                                  
CONECT   20   14   18   25                                                  
CONECT   21   13                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   19                                                            
CONECT   25   10   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0038902
HETATM    1  C1  UNL     1       5.108   2.764   0.349  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.606   1.366   0.590  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.618   0.325   0.823  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.298   1.131   0.586  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.677  -0.179   0.806  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.836  -0.630  -0.354  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.329  -1.116  -1.514  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.730  -1.209  -1.651  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.509  -1.500  -2.509  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.100  -1.404  -2.367  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.692  -1.802  -3.394  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.448  -0.913  -1.198  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.802  -0.782  -0.965  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.600  -1.128  -1.867  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.302  -0.275   0.244  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.696  -0.131   0.503  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.526   0.417  -0.469  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.862   0.528  -0.151  1.00  0.00           C  
HETATM   19  C16 UNL     1      -6.400   0.131   1.054  1.00  0.00           C  
HETATM   20  O4  UNL     1      -7.775   0.277   1.304  1.00  0.00           O  
HETATM   21  C17 UNL     1      -5.564  -0.410   2.005  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.220  -0.542   1.735  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.341   0.074   1.164  1.00  0.00           C  
HETATM   24  O5  UNL     1      -0.059  -0.064   0.910  1.00  0.00           O  
HETATM   25  C20 UNL     1       0.447  -0.529  -0.198  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.985   2.996   0.993  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.373   2.894  -0.730  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.294   3.450   0.602  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.538   0.592   0.237  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.344  -0.684   0.506  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.967   0.349   1.898  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.616   1.962   0.406  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.058  -0.109   1.724  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.392  -1.004   0.984  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.114  -1.569  -2.509  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.872  -1.890  -3.442  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.630  -1.837  -3.542  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.114   0.733  -1.421  1.00  0.00           H  
HETATM   39  H14 UNL     1      -6.507   0.954  -0.906  1.00  0.00           H  
HETATM   40  H15 UNL     1      -8.189  -0.004   2.174  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.919  -0.739   2.965  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.569  -0.969   2.489  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.593   0.477   2.135  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4    4
CONECT    3   29   30   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    7   25
CONECT    7    8    9
CONECT    8   35
CONECT    9   10   10   36
CONECT   10   11   12
CONECT   11   37
CONECT   12   13   25   25
CONECT   13   14   14   15
CONECT   15   16   23   23
CONECT   16   17   17   22
CONECT   17   18   38
CONECT   18   19   19   39
CONECT   19   20   21
CONECT   20   40
CONECT   21   22   22   41
CONECT   22   42
CONECT   23   24   43
CONECT   24   25
END

HMDB0038902
     RDKit          3D
Lupiwighteone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1077    2.7635    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    1.3655    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176    0.3248    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2979    1.1314    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773   -0.1790    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -0.6296   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287   -1.1158   -1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7297   -1.2089   -1.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5091   -1.4998   -2.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999   -1.4044   -2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6920   -1.8019   -3.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4484   -0.9130   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8021   -0.7816   -0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -1.1283   -1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -0.2754    0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -0.1314    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    0.4170   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8620    0.5280   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4002    0.1315    1.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7751    0.2774    1.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639   -0.4099    2.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2198   -0.5420    1.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    0.0741    1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0587   -0.0638    0.9097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -0.5291   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9848    2.9959    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3735    2.8935   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    3.4500    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5376    0.5916    0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3438   -0.6844    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668    0.3488    1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164    1.9615    0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -0.1088    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3924   -1.0035    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -1.5693   -2.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718   -1.8899   -3.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6297   -1.8373   -3.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140    0.7329   -1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5074    0.9542   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1890   -0.0043    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9194   -0.7390    2.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5695   -0.9686    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929    0.4772    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  2  0
 23 24  1  0
 24 25  1  0
 25  6  1  0
 25 12  2  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7,4'-Trihydroxy-8-prenylisoflavone	HMDB
5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₈O₅

Average Molecular Weight

338.3539

Monoisotopic Molecular Weight

338.115423686

IUPAC Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

lupiwighteone

CAS Registry Number

104691-86-3

SMILES

CC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17(23)18-19(24)15(10-25-20(14)18)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3

InChI Key

YGCCASGFIOIXIN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050196 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038902)

Cellular substructure

Membrane (HMDB: HMDB0038902)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038902)

Source

Exogenous

Food

Food (HMDB: HMDB0038902)

Pulse

Bean

Adzuki bean (FooDB: FOOD00198)

Pulses (FooDB: FOOD00867)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0038902)
Fabaceae (HMDB: HMDB0038902)

Not Available

Nutrient (HMDB: HMDB0038902)

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.92	ALOGPS
logP	4.81	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	6.42	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.93 m³·mol⁻¹	ChemAxon
Polarizability	36.13 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
DeepCCS	[M+H]+	179.765	30932474
DeepCCS	[M-H]-	177.391	30932474
DeepCCS	[M-2H]-	211.698	30932474
DeepCCS	[M+Na]+	186.931	30932474
AllCCS	[M+H]+	181.3	32859911
AllCCS	[M+H-H2O]+	178.0	32859911
AllCCS	[M+NH4]+	184.4	32859911
AllCCS	[M+Na]+	185.3	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	179.8	32859911
AllCCS	[M+HCOO]-	179.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lupiwighteone	CC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1	4716.3	Standard polar	33892256
Lupiwighteone	CC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1	3187.0	Standard non polar	33892256
Lupiwighteone	CC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1	3314.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lupiwighteone,1TMS,isomer #1	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1)C2=O	3343.6	Semi standard non polar	33892256
Lupiwighteone,1TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1)C2=O	3361.3	Semi standard non polar	33892256
Lupiwighteone,1TMS,isomer #3	CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1)C2=O	3335.4	Semi standard non polar	33892256
Lupiwighteone,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1)C2=O	3218.7	Semi standard non polar	33892256
Lupiwighteone,2TMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1)C2=O	3195.7	Semi standard non polar	33892256
Lupiwighteone,2TMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1)C2=O	3183.2	Semi standard non polar	33892256
Lupiwighteone,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1)C2=O	3150.6	Semi standard non polar	33892256
Lupiwighteone,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1)C2=O	3620.4	Semi standard non polar	33892256
Lupiwighteone,1TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1)C2=O	3629.6	Semi standard non polar	33892256
Lupiwighteone,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C2=O	3601.6	Semi standard non polar	33892256
Lupiwighteone,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1)C2=O	3715.2	Semi standard non polar	33892256
Lupiwighteone,2TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C2=O	3717.7	Semi standard non polar	33892256
Lupiwighteone,2TBDMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C2=O	3711.1	Semi standard non polar	33892256
Lupiwighteone,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C2=O	3885.4	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 - Lupiwighteone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2039000000-e00b09a7113c52ef519c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lupiwighteone GC-MS (3 TMS) - 70eV, Positive	splash10-052u-2020490000-90b5bf81041d037ca2b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lupiwighteone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lupiwighteone 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 - Lupiwighteone 10V, Positive-QTOF	splash10-000i-0029000000-e7d39ee05da79ec48e5a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 20V, Positive-QTOF	splash10-00ss-4098000000-5fcb0ef56db30978ce62	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 40V, Positive-QTOF	splash10-0gb9-9252000000-ef02e260841cffc23ef4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 10V, Negative-QTOF	splash10-000i-0009000000-b33c9ee6a45ae620db11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 20V, Negative-QTOF	splash10-000i-0039000000-a885742fe68845f945cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 40V, Negative-QTOF	splash10-00kf-8962000000-1d677ca23483a47ac22e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 10V, Positive-QTOF	splash10-0019-0069000000-5ae6f2800554c558236b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 20V, Positive-QTOF	splash10-001i-0090000000-2d1c6e849385d2297c9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 40V, Positive-QTOF	splash10-0159-0290000000-83a295ca4d8a73c5b19e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 10V, Negative-QTOF	splash10-000i-0009000000-fba49930c01349472a4d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 20V, Negative-QTOF	splash10-000i-0019000000-6e13d8533b5313652e00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupiwighteone 40V, Negative-QTOF	splash10-00lr-0971000000-d3b1ad42f1c6d48203fc	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

FDB018366

KNApSAcK ID

C00009896

Chemspider ID

4476335

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317480

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1872561

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 Lupiwighteone (HMDB0038902)

MOL for HMDB0038902 (Lupiwighteone)

3D MOL for HMDB0038902 (Lupiwighteone)

3D SDF for HMDB0038902 (Lupiwighteone)

3D-SDF for HMDB0038902 (Lupiwighteone)

PDB for HMDB0038902 (Lupiwighteone)

3D PDB for HMDB0038902 (Lupiwighteone)

SMILES for HMDB0038902 (Lupiwighteone)

INCHI for HMDB0038902 (Lupiwighteone)

Structure for HMDB0038902 (Lupiwighteone)

3D Structure for HMDB0038902 (Lupiwighteone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra