NP-MRD: Showing NP-Card for Diplacone (NP0055646)

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Record Information

Version

2.0

Created at

2022-04-28 01:38:23 UTC

Updated at

2022-04-28 01:38:24 UTC

NP-MRD ID

NP0055646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diplacone

Description

Nymphaeol A, also known as propolin C, belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position. Nymphaeol A 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. Diplacone is found in Diplacus aurantiacus, Diplacus clevelandii, Hernandia nymphaeifolia , Macaranga alnifolia, Macaranga tanarius, Paulownia tomentosa and Schizolaena hystrix. Diplacone was first documented in 2012 (PMID: 21790499). Based on a literature review a small amount of articles have been published on nymphaeol A (PMID: 33641170) (PMID: 31448698).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203382D          

 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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
   -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 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
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
  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
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 23 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
   -8.6585    0.1758   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7596    0.0651   -0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1841    0.6264    1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5648   -0.5426   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7139   -0.6273    1.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4341    0.1185    0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5031   -0.2877   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8385   -0.1398   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356   -0.7728    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140   -1.2129   -0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072   -0.5359   -0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559    0.7627   -0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132    1.5215   -1.4454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053    1.2879   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4833    0.5551    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -0.7654    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.3324    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6845   -2.6292    0.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2531   -1.4964    1.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821   -2.4152    1.9035 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -1.1123    0.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8143    0.3934    0.9323 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1155    0.7375    0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4496    2.0574    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6712    2.3647   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5728    1.3925   -0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8026    1.7057   -1.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2637    0.0623   -0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1664   -0.9304   -0.8824 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0459   -0.2420   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7293    1.0812    0.3907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4814    1.1430   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4153   -0.6429   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7214    0.0401   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3182   -0.1550    1.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4512    1.4004    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1630    1.1709    1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2765   -0.9765   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2891   -0.2233    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4776   -1.6984    1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6920    1.2144    0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9343    0.0039    1.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6826    0.6048   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1041   -1.1088   -1.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146    0.3320   -2.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -0.8594    1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844   -2.3089   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5621   -0.9838   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6034    2.4666   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    2.3083   -0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -3.2900    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -1.6141    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -1.3761   -0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633    0.6435    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    2.8547    0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9340    3.4036   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4678    0.9833   -1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9464   -1.8970   -0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8380   -1.3006    0.1635 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 31  1  0
 31 22  1  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
 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  1  0
 28 30  2  0
 17 11  1  0
 30 23  1  0
 16 15  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
 22 54  1  1
 21 52  1  0
 21 53  1  0
 18 51  1  0
 24 55  1  0
 25 56  1  0
 27 57  1  0
 29 58  1  0
 30 59  1  0
M  END


  Mrv1652304282203382D          

 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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
   -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 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
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
  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
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=C(O)C=C2O[C@@H](CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

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

> <INCHI_KEY>
XCYSQFHYFNWYFP-CEMXSPGASA-N

> <FORMULA>
C25H28O6

> <MOLECULAR_WEIGHT>
424.493

> <EXACT_MASS>
424.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.39696443831012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.61

> <JCHEM_LOGP>
5.9198240030000004

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.977873096345853

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.66880198075499

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9505939789350215

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
121.3161

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.37e-03 g/l

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

> <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  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+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   21                                                  
CONECT    3    2    4   20                                                  
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                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20    3                                                            
CONECT   21    2   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
6-Geranyl-3',4',5,7-tetrahydroxyflavanone	ChEBI
Propolin C	MeSH

Chemical Formula

C₂₅H₂₈O₆

Average Mass

424.4930 Da

Monoisotopic Mass

424.18859 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC1=C(O)C=C2O[C@@H](CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

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

InChI Key

XCYSQFHYFNWYFP-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
Diplacus aurantiacus	Plant	KNApSAcK
Diplacus clevelandii	LOTUS Database	35616633
Hernandia nymphaeifolia	Plant	KNApSAcK
Macaranga alnifolia	Plant	KNApSAcK
Macaranga tanarius	LOTUS Database	35616633
Paulownia tomentosa	Plant	KNApSAcK
Schizolaena hystrix	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

6-prenylated flavanones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavanone (CHEBI:66640 )

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	4.61	ALOGPS
logP	5.92	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.67	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	45.4 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

Not Available

Chemspider ID

554888

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

639465

PDB ID

Not Available

ChEBI ID

66640

Good Scents ID

Not Available

References

General References

Nam SH, Yamano A, Kim JA, Lim J, Baek SH, Kim JE, Kwon TG, Saito Y, Teruya T, Choi SY, Kim YK, Bae YC, Shin HI, Woo JT, Park EK: Prenylflavonoids isolated from Macaranga tanarius stimulate odontoblast differentiation of human dental pulp stem cells and tooth root formation via the mitogen-activated protein kinase and protein kinase B pathways. Int Endod J. 2021 Jul;54(7):1142-1154. doi: 10.1111/iej.13503. Epub 2021 Mar 30. [PubMed:33641170 ]
Shahinozzaman M, Ishii T, Ahmed S, Halim MA, Tawata S: A computational approach to explore and identify potential herbal inhibitors for the p21-activated kinase 1 (PAK1). J Biomol Struct Dyn. 2020 Aug;38(12):3514-3526. doi: 10.1080/07391102.2019.1659855. Epub 2019 Sep 5. [PubMed:31448698 ]
Chen CN, Hsiao CJ, Lee SS, Guh JH, Chiang PC, Huang CC, Huang WJ: Chemical modification and anticancer effect of prenylated flavanones from Taiwanese propolis. Nat Prod Res. 2012;26(2):116-24. doi: 10.1080/14786419.2010.535146. Epub 2011 Jul 27. [PubMed:21790499 ]

Showing NP-Card for Diplacone (NP0055646)

MOL for NP0055646 (Diplacone)

3D MOL for NP0055646 (Diplacone)

3D SDF for NP0055646 (Diplacone)

3D-SDF for NP0055646 (Diplacone)

PDB for NP0055646 (Diplacone)

3D PDB for NP0055646 (Diplacone)

SMILES for NP0055646 (Diplacone)

INCHI for NP0055646 (Diplacone)

Structure for NP0055646 (Diplacone)

3D Structure for NP0055646 (Diplacone)