NP-MRD: Showing NP-Card for 6,8-Diprenylnaringenin (NP0137664)

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Record Information

Version

2.0

Created at

2022-05-31 16:02:31 UTC

Updated at

2022-05-31 16:02:31 UTC

NP-MRD ID

NP0137664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,8-Diprenylnaringenin

Description

6,8-Diprenylnaringenin, also known as senegalensin or lonchocarpol a, belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, 6,8-diprenylnaringenin is considered to be a flavonoid. 6,8-Diprenylnaringenin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 6,8-Diprenylnaringenin is found in Citrus limon, Citrus medica, Citrus natsudaidai, Citrus nobilis, Derris laxiflora, Erythrina fusca, Erythrina senegalensis, Erythrina sigmoidea, Erythrina suberosa, Flemingia macrophylla, Glycyrrhiza pallidiflora, Humulus lupulus, Limonia acidissima, Lonchocarpus minimiflorus, Lupinus luteus, Macaranga conifera, Maclura tricuspidata, Melipotis perpendicularis, Monotes engleri and Sophora tetraptera. 6,8-Diprenylnaringenin was first documented in 1998 (PMID: 9599265). Based on a literature review a small amount of articles have been published on 6,8-diprenylnaringenin (PMID: 32937790) (PMID: 18478479) (PMID: 11325248) (PMID: 16972201).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218022D          

 31 33  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -2.8875    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    1.4289   -1.6500    0.0000 O   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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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   -2.8875    0.0000 O   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  2  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    5.9650   -1.5733   -0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5752   -0.7157    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3347   -0.9079    1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285    0.1797    0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7725    0.5034   -0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3365    0.2969   -0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4341    1.2864   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437    2.5924   -0.1291 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099    1.0108    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9048    2.0771    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3427    2.7853   -0.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2544    4.0925   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    4.6447   -2.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122    5.0204    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -0.2865    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5610   -1.2990   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8846   -1.0284   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7545   -2.0544   -0.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0233   -2.6579   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225   -3.6017   -0.6127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -2.8525    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2069   -1.8201    0.0533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6154   -2.0277    0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387   -1.6894    1.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5854   -1.9255    1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3689   -2.4997    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7395   -2.7325    0.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7590   -2.8427   -0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4117   -2.6051   -0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125   -0.5551    0.4303 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0524   -1.8154   -0.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8981   -1.0209   -1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533   -2.5366   -0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1256   -0.1182    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0176   -1.8735    2.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3998   -0.9796    1.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075    0.7623    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0803   -0.1168   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9548    1.5471   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360    2.9791   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    1.6974    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577    2.8402    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657    2.1470   -1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1617    4.1743   -3.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834    4.2367   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7305    5.7438   -2.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848    4.7611    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4085    5.1440    0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6090    6.0406   -0.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016   -3.0127   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -3.8776    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882   -2.5988    1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455   -1.8731   -1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6362   -1.2386    2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0774   -1.6599    2.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3637   -1.9631    0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3260   -3.3033   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9818   -2.8997   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19 16  1  0
 16 17  2  0
 17 18  1  0
 17  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15 30  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 30 22  1  0
 29 23  1  0
 15 16  1  0
 22 53  1  6
 21 51  1  0
 21 52  1  0
 18 50  1  0
  5 38  1  0
  5 39  1  0
  4 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
M  END


  Mrv1652305312218022D          

 31 33  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -2.8875    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    1.4289   -1.6500    0.0000 O   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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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   -2.8875    0.0000 O   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  2  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC(=O)C2=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C2O1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3/t21-/m0/s1

> <INCHI_KEY>
HCNLDGTUMBOHKT-NRFANRHFSA-N

> <FORMULA>
C25H28O5

> <MOLECULAR_WEIGHT>
408.494

> <EXACT_MASS>
408.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.005081124949925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
6.292242049000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.070829382591645

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.508271233960288

> <JCHEM_PKA_STRONGEST_BASIC>
-4.961077727446398

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
119.7754

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
lonchocarpol A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.334  -2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24   25                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   23                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17    6   24                                                  
CONECT   24   23    2                                                       
CONECT   25    2   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Lonchocarpol a	ChEBI
Senegalensin	ChEBI
5,4'-Dihydroxy-8-(gamma,gamma-dimethylallyl)-(5''-(hydroxyisopropyl)dihydrofurano(2'',3''-6.7))isoflavone	MeSH

Chemical Formula

C₂₅H₂₈O₅

Average Mass

408.4940 Da

Monoisotopic Mass

408.19367 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

68236-11-3

SMILES

[H][C@]1(CC(=O)C2=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C2O1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3/t21-/m0/s1

InChI Key

HCNLDGTUMBOHKT-NRFANRHFSA-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
Citrus limon	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus natsudaidai	LOTUS Database	35616633
Citrus nobilis	LOTUS Database	35616633
Derris laxiflora	LOTUS Database	35616633
Erythrina fusca	LOTUS Database	35616633
Erythrina senegalensis	LOTUS Database	35616633
Erythrina sigmoidea	LOTUS Database	35616633
Erythrina suberosa	LOTUS Database	35616633
Flemingia macrophylla	LOTUS Database	35616633
Glycyrrhiza pallidiflora	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Limonia acidissima	LOTUS Database	35616633
Lonchocarpus minimiflorus	LOTUS Database	35616633
Lupinus luteus	LOTUS Database	35616633
Macaranga conifera	LOTUS Database	35616633
Maclura tricuspidata	LOTUS Database	35616633
Melipotis perpendicularis	LOTUS Database	35616633
Monotes engleri	LOTUS Database	35616633
Sophora tetraptera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavanone (CHEBI:2156 )
flavanones (C09724 )
Flavanones (LMPK12140276 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000954

Chemspider ID

110549

KEGG Compound ID

C09724

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124035

PDB ID

Not Available

ChEBI ID

2156

Good Scents ID

Not Available

References

General References

Tronina T, Poplonski J, Bartmanska A: Flavonoids as Phytoestrogenic Components of Hops and Beer. Molecules. 2020 Sep 14;25(18). pii: molecules25184201. doi: 10.3390/molecules25184201. [PubMed:32937790 ]
Clarke DB, Bailey V, Lloyd AS: Determination of phytoestrogens in dietary supplements by LC-MS/MS. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2008 May;25(5):534-47. doi: 10.1080/02652030701658340. [PubMed:18478479 ]
Meragelman KM, McKee TC, Boyd MR: Anti-HIV prenylated flavonoids from Monotes africanus. J Nat Prod. 2001 Apr;64(4):546-8. doi: 10.1021/np0005457. [PubMed:11325248 ]
Bae EY, Na M, Njamen D, Mbafor JT, Fomum ZT, Cui L, Choung DH, Kim BY, Oh WK, Ahn JS: Inhibition of protein tyrosine phosphatase 1B by prenylated isoflavonoids isolated from the stem bark of Erythrina addisoniae. Planta Med. 2006 Aug;72(10):945-8. doi: 10.1055/s-2006-946674. [PubMed:16972201 ]
Salvatore MJ, King AB, Graham AC, Onishi HR, Bartizal KF, Abruzzo GK, Gill CJ, Ramjit HG, Pitzenberger SM, Witherup KM: Antibacterial activity of lonchocarpol A. J Nat Prod. 1998 May;61(5):640-2. doi: 10.1021/np9703961. [PubMed:9599265 ]

Showing NP-Card for 6,8-Diprenylnaringenin (NP0137664)

MOL for NP0137664 (6,8-Diprenylnaringenin)

3D MOL for NP0137664 (6,8-Diprenylnaringenin)

3D SDF for NP0137664 (6,8-Diprenylnaringenin)

3D-SDF for NP0137664 (6,8-Diprenylnaringenin)

PDB for NP0137664 (6,8-Diprenylnaringenin)

3D PDB for NP0137664 (6,8-Diprenylnaringenin)

SMILES for NP0137664 (6,8-Diprenylnaringenin)

INCHI for NP0137664 (6,8-Diprenylnaringenin)

Structure for NP0137664 (6,8-Diprenylnaringenin)

3D Structure for NP0137664 (6,8-Diprenylnaringenin)