NP-MRD: Showing NP-Card for 5,7,2',4'-Tetrahydroxy-3'-geranylflavanone (NP0060446)

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Record Information

Version

2.0

Created at

2022-04-28 05:29:52 UTC

Updated at

2022-04-28 05:29:52 UTC

NP-MRD ID

NP0060446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,2',4'-Tetrahydroxy-3'-geranylflavanone

Description

Sanggenol a belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position. Thus, sanggenol a is considered to be a flavonoid. 5,7,2',4'-Tetrahydroxy-3'-geranylflavanone is found in Morus cathayana. 5,7,2',4'-Tetrahydroxy-3'-geranylflavanone was first documented in 2010 (PMID: 20815207). Based on a literature review a small amount of articles have been published on Sanggenol a (PMID: 27257160) (PMID: 25981820) (PMID: 33733438) (PMID: 34946724).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282207292D          

 31 33  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    2.8579    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
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   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
    3.5724    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 13 29  1  0  0  0  0
  3 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -6.5513    0.4543    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1770   -0.5250    0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7019   -0.6867    0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5803   -1.2570   -0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886   -1.3488   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1483   -0.6216    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8095   -0.8730   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963   -2.2352   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726    0.1746   -0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685    0.0681   -1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1990    0.9040   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884    2.2636   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499    2.8868   -2.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1852    3.0172   -0.6163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1425    2.4422    0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0911    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1720    0.4154    1.2842 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0702    1.3830    2.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2448    1.7061    1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6316    2.8445    0.8482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873    0.5799    0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3348    0.5910    0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0696    1.7174    0.5940 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9796   -0.5265   -0.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2440   -1.6387   -0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8220   -2.8043   -1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8851   -1.6794   -0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377   -0.5600    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8949   -0.5574    0.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604    0.3321   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038   -1.0117    0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6951    0.1034    2.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3311    0.7740    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2787    1.3936    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1315    0.1015    0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9235   -0.5625    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9625   -1.7173    0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2729   -1.9566   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9450   -2.4621   -0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0643   -1.0517   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3294    0.4577    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -1.0730    1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8456   -2.4814   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -3.0212   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670   -2.4613    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228    1.1837   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5394   -0.9768   -1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881    0.4688   -2.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4677    2.3816   -2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593    4.0812   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128    3.0763    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334   -0.1630    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838    0.8237    2.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    2.2556    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7357    2.5429    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0229   -0.4918   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1909   -3.5274   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2872   -2.5624   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5743   -1.6816   -0.3271 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  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 16 30  2  0
 30 31  1  0
 30 11  1  0
 29 17  1  0
 28 21  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
  6 41  1  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  0
 17 52  1  1
 18 53  1  0
 18 54  1  0
 23 55  1  0
 24 56  1  0
 26 57  1  0
 27 58  1  0
 31 59  1  0
M  END

  Mrv1652304282207292D          

 31 33  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    2.8579    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
    4.2868    0.8250    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
    3.5724   -0.4125    0.0000 C   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
    3.5724    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 13 29  1  0  0  0  0
  3 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=C(O)C=CC([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O6/c1-14(2)5-4-6-15(3)7-8-17-19(27)10-9-18(25(17)30)22-13-21(29)24-20(28)11-16(26)12-23(24)31-22/h5,7,9-12,22,26-28,30H,4,6,8,13H2,1-3H3/b15-7+/t22-/m0/s1

> <INCHI_KEY>
QNPMSYLDWCXEOI-CEMXSPGASA-N

> <FORMULA>
C25H28O6

> <MOLECULAR_WEIGHT>
424.493

> <EXACT_MASS>
424.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.70878037939758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
5.9198240030000004

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.747161128157051

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.815602312905639

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950691457342234

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
121.3161

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sanggenol A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668   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  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   13                                                            
CONECT   30    3                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₆

Average Mass

424.4930 Da

Monoisotopic Mass

424.18859 Da

IUPAC Name

(2S)-2-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

sanggenol A

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC1=C(O)C=CC([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)=C1O

InChI Identifier

InChI=1S/C25H28O6/c1-14(2)5-4-6-15(3)7-8-17-19(27)10-9-18(25(17)30)22-13-21(29)24-20(28)11-16(26)12-23(24)31-22/h5,7,9-12,22,26-28,30H,4,6,8,13H2,1-3H3/b15-7+/t22-/m0/s1

InChI Key

QNPMSYLDWCXEOI-CEMXSPGASA-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
Morus cathayana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

3'-prenylated flavanones

Alternative Parents

Substituents

3'-prenylated flavanone
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Bicyclic monoterpenoid
Aromatic monoterpenoid
Benzopyran
1-benzopyran
Monoterpenoid
Chromane
Aryl alkyl ketone
Aryl ketone
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140495 )

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	4.57	ALOGPS
logP	5.92	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.32 m³·mol⁻¹	ChemAxon
Polarizability	45.71 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00014187

Chemspider ID

24846516

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15233693

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Grienke U, Richter M, Walther E, Hoffmann A, Kirchmair J, Makarov V, Nietzsche S, Schmidtke M, Rollinger JM: Discovery of prenylated flavonoids with dual activity against influenza virus and Streptococcus pneumoniae. Sci Rep. 2016 Jun 3;6:27156. doi: 10.1038/srep27156. [PubMed:27257160 ]
Jung JW, Ko WM, Park JH, Seo KH, Oh EJ, Lee DY, Lee DS, Kim YC, Lim DW, Han D, Baek NI: Isoprenylated flavonoids from the root bark of Morus alba and their hepatoprotective and neuroprotective activities. Arch Pharm Res. 2015 Nov;38(11):2066-75. doi: 10.1007/s12272-015-0613-8. Epub 2015 May 16. [PubMed:25981820 ]
Bai Y, Chen L, Cao YF, Hou XD, Jia SN, Zhou Q, He YQ, Hou J: Beta-Glucuronidase Inhibition by Constituents of Mulberry Bark. Planta Med. 2021 Jul;87(8):631-641. doi: 10.1055/a-1402-6431. Epub 2021 Mar 17. [PubMed:33733438 ]
Ko W, Liu Z, Kim KW, Dong L, Lee H, Kim NY, Lee DS, Woo ER: Kuwanon T and Sanggenon a Isolated from Morus alba Exert Anti-Inflammatory Effects by Regulating NF-kappaB and HO-1/Nrf2 Signaling Pathways in BV2 and RAW264.7 Cells. Molecules. 2021 Dec 16;26(24). pii: molecules26247642. doi: 10.3390/molecules26247642. [PubMed:34946724 ]
Geng C, Yao S, Xue D, Zuo A, Zhang X, Jiang Z, Ma Y, Chen J: New isoprenylated flavonoid from Morus alba. Zhongguo Zhong Yao Za Zhi. 2010 Jun;35(12):1560-5. [PubMed:20815207 ]

Showing NP-Card for 5,7,2',4'-Tetrahydroxy-3'-geranylflavanone (NP0060446)

MOL for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

3D MOL for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

3D SDF for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

3D-SDF for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

PDB for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

3D PDB for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

SMILES for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

INCHI for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

Structure for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)

3D Structure for NP0060446 (5,7,2',4'-Tetrahydroxy-3'-geranylflavanone)