NP-MRD: Showing NP-Card for 5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone (NP0056933)

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Record Information

Version

2.0

Created at

2022-04-28 02:31:42 UTC

Updated at

2022-04-28 02:31:42 UTC

NP-MRD ID

NP0056933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone

Description

Isoangustone A belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, isoangustone a is considered to be a flavonoid lipid molecule. Isoangustone A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isoangustone A has been detected, but not quantified in, herbs and spices. 5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone is found in Glycyrrhiza glabra , Glycyrrhiza inflata and Glycyrrhiza uralensis . This could make isoangustone a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310432D          

 31 33  0  0  0  0            999 V2000
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    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
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    1.4289    0.8250    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
    7.8592    2.0625    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
    5.7158    2.4750    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
    0.7145    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
    0.7145    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
    2.1434    1.2375    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
    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
    2.8579    2.4750    0.0000 C   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
    5.0013    4.5375    0.0000 O   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
    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
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  5  2  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14  6  2  0  0  0  0
 15  7  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17  8  1  0  0  0  0
 18 12  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 19 17  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  1  0  0  0  0
 22 21  2  0  0  0  0
 23 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 17  2  0  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 25 22  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31 12  1  0  0  0  0
 31 21  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -7.6858   -1.2041    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4762   -1.8741    0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6088   -2.9914    1.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2839   -1.5279    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917   -0.4419   -0.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1379    0.5371   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    0.4736   -0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330    1.3088   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983    1.1818   -0.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694    1.0695   -2.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9253    0.9536   -2.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0107    0.9331   -2.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    0.8074   -2.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139    0.7826   -1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6753    0.6563   -2.4243 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883    0.8884   -0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5440    0.8590    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -0.4967    0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5951   -1.3389    0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5849   -2.6700    1.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7288   -0.9857   -0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453    1.0176    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219    1.1155    1.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981    1.0403   -0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380    1.1643   -0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    1.2624    1.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933    2.2125    0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    2.2911    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    3.1977    2.1138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595    1.4368    0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7587    1.4877    1.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6999   -1.1035   -1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7612   -0.1967    0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5842   -1.8263    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6191   -3.2155    1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0350   -3.8448    0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2867   -2.5760    2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4165   -2.0608    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0680    0.0601   -1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7096   -0.8449   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5730   -0.2468   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1717    1.0851   -2.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3349    0.7268   -3.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8193    0.5750   -3.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5234    1.6604    1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4162    1.0728   -0.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727   -0.7629    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9354   -2.6196    2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2311   -3.3958    0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6083   -2.9963    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5882   -1.6955   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4862   -1.0340   -1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1507    0.0225    0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706    1.2153    2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4310    2.8788    1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504    3.8296    2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9996    2.1467    1.8342 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
  8 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 24  2  0
 24 22  1  0
 22 23  1  0
 22 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
 24 25  1  0
 25 26  2  0
 30  6  1  0
 25  9  1  0
 13 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
 27 55  1  0
 29 56  1  0
 31 57  1  0
 10 42  1  0
 23 54  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 15 44  1  0
 13 43  1  0
M  END


  Mrv0541 05061310432D          

 31 33  0  0  0  0            999 V2000
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    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
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    1.4289    0.8250    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
    7.8592    2.0625    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
    5.7158    2.4750    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
    0.7145    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
    0.7145    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
    2.1434    1.2375    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
    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
    2.8579    2.4750    0.0000 C   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
    5.0013    4.5375    0.0000 O   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
    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
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  5  2  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14  6  2  0  0  0  0
 15  7  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17  8  1  0  0  0  0
 18 12  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 19 17  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  1  0  0  0  0
 22 21  2  0  0  0  0
 23 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 17  2  0  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 25 22  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31 12  1  0  0  0  0
 31 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O6/c1-13(2)5-7-15-9-16(10-20(27)23(15)28)18-12-31-21-11-19(26)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-12,26-29H,7-8H2,1-4H3

> <INCHI_KEY>
QNLGNISMYMFVHP-UHFFFAOYSA-N

> <FORMULA>
C25H26O6

> <MOLECULAR_WEIGHT>
422.4703

> <EXACT_MASS>
422.172938564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.804669753505465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
6.230441066666666

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.449360709096

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.418737207380767

> <JCHEM_PKA_STRONGEST_BASIC>
-5.231601724739655

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
122.14939999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoangustone A

> <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      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667   6.160   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  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    7   13                                                       
CONECT    6    8   14                                                       
CONECT    7    5   15                                                       
CONECT    8    6   17                                                       
CONECT    9   15   16                                                       
CONECT   10   16   20                                                       
CONECT   11   19   21                                                       
CONECT   12   18   31                                                       
CONECT   13    1    2    5                                                  
CONECT   14    3    4    6                                                  
CONECT   15    7    9   23                                                  
CONECT   16    9   10   18                                                  
CONECT   17    8   19   24                                                  
CONECT   18   12   16   25                                                  
CONECT   19   11   17   26                                                  
CONECT   20   10   23   27                                                  
CONECT   21   11   22   31                                                  
CONECT   22   21   24   25                                                  
CONECT   23   15   20   28                                                  
CONECT   24   17   22   29                                                  
CONECT   25   18   22   30                                                  
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   25                                                            
CONECT   31   12   21                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
3-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone	HMDB

Chemical Formula

C₂₅H₂₆O₆

Average Mass

422.4703 Da

Monoisotopic Mass

422.17294 Da

IUPAC Name

3-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

isoangustone A

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O

InChI Identifier

InChI=1S/C25H26O6/c1-13(2)5-7-15-9-16(10-20(27)23(15)28)18-12-31-21-11-19(26)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-12,26-29H,7-8H2,1-4H3

InChI Key

QNLGNISMYMFVHP-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050243 )

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	4.6	ALOGPS
logP	6.23	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	6.42	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.15 m³·mol⁻¹	ChemAxon
Polarizability	46.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038905

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018369

KNApSAcK ID

C00009922

Chemspider ID

10211375

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21591148

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone (NP0056933)

MOL for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

3D MOL for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

3D SDF for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

3D-SDF for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

PDB for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

3D PDB for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

SMILES for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

INCHI for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

Structure for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)

3D Structure for NP0056933 (5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone)