NP-MRD: Showing NP-Card for 8-geranyl-3',4',7-trihydroxyflavone (NP0032216)

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Record Information

Version

2.0

Created at

2021-06-19 23:04:43 UTC

Updated at

2021-06-30 00:01:16 UTC

NP-MRD ID

NP0032216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-geranyl-3',4',7-trihydroxyflavone

Provided By

JEOL Database JEOL Logo

Description

2-(3,4-Dihydroxyphenyl)-8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-4H-chromen-4-one belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. 8-geranyl-3',4',7-trihydroxyflavone is found in Artocarpus nobilis and Artocarpus nobilis. 8-geranyl-3',4',7-trihydroxyflavone was first documented in 2006 (Jayasinghe, L., et al.). Based on a literature review very few articles have been published on 2-(3,4-dihydroxyphenyl)-8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-4H-chromen-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101043D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202101043D          

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    1.2210   -0.1666    0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -1.4805    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4884   -1.6674    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5986   -1.7324    4.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    0.5541    4.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379    0.8703    2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    0.3524    5.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9178    4.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510    1.6582    2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5785    1.4642    1.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4571   -0.8691    5.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -0.5674    4.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5638    0.1945    3.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7873   -3.8979    5.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -5.2583    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322   -5.4197    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869   -2.1634   -2.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    1.3011   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    3.5131   -1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872    3.9561   -3.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192    1.2174   -3.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832   -0.2755   -2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 26  1  0  0  0  0
 12 11  2  0  0  0  0
 26 28  2  0  0  0  0
 28 21  1  0  0  0  0
 11 30  1  0  0  0  0
 12 13  1  0  0  0  0
 30 29  1  0  0  0  0
 11 10  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 26 27  1  0  0  0  0
 19 20  2  0  0  0  0
 24 25  1  0  0  0  0
 20 29  1  0  0  0  0
 10  9  1  0  0  0  0
 30 16  2  0  0  0  0
  9  7  2  0  0  0  0
 20 21  1  0  0  0  0
  7  6  1  0  0  0  0
 15 14  2  0  0  0  0
  6  5  1  0  0  0  0
 21 22  2  0  0  0  0
  5  4  1  0  0  0  0
 16 15  1  0  0  0  0
  4  2  2  3  0  0  0
 22 23  1  0  0  0  0
  2  1  1  0  0  0  0
 14 12  1  0  0  0  0
  2  3  1  0  0  0  0
 23 24  2  0  0  0  0
  7  8  1  0  0  0  0
 15 50  1  0  0  0  0
 14 49  1  0  0  0  0
 19 51  1  0  0  0  0
 22 52  1  0  0  0  0
 23 53  1  0  0  0  0
 28 56  1  0  0  0  0
 13 48  1  0  0  0  0
 10 46  1  0  0  0  0
 10 47  1  0  0  0  0
 27 55  1  0  0  0  0
 25 54  1  0  0  0  0
  9 45  1  0  0  0  0
  6 40  1  0  0  0  0
  6 41  1  0  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
  4 37  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1O[H])C1=C([H])C(=O)C2=C(O1)C(=C(O[H])C([H])=C2[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O5/c1-15(2)5-4-6-16(3)7-9-18-20(26)12-10-19-22(28)14-24(30-25(18)19)17-8-11-21(27)23(29)13-17/h5,7-8,10-14,26-27,29H,4,6,9H2,1-3H3/b16-7+

> <INCHI_KEY>
SWGONUIXZUDUSG-FRKPEAEDSA-N

> <FORMULA>
C25H26O5

> <MOLECULAR_WEIGHT>
406.478

> <EXACT_MASS>
406.178023937

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.40690333000168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
5.444970408000001

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.705303344931782

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.314319823054818

> <JCHEM_PKA_STRONGEST_BASIC>
-5.38157823339923

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
120.95929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    1.3983   -3.3634    2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4403   -1.8572    2.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465   -1.2506    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436   -1.1680    3.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984    0.3258    3.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1861   -1.9189    3.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -3.0965    3.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604   -3.0058    5.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4059   -4.3504    3.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478   -4.4461    1.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6240   -3.3712   -0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832   -4.4380   -1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -2.1031   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162   -0.9590   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1693    0.3454   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    1.4279   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016    2.6808   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152    2.8515   -2.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931    4.0757   -2.7809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526    1.7938   -2.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2041    2.0374   -3.3267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689    0.5418   -1.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6898   -0.8759    0.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9237   -2.0319    1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -3.7197    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4736   -3.7751    3.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2287   -3.7696    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4884   -1.6674    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5986   -1.7324    4.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    0.5541    4.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379    0.8703    2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    0.3524    5.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9178    4.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510    1.6582    2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5785    1.4642    1.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108    2.7056    2.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571   -0.8691    5.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -0.5674    4.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5638    0.1945    3.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7873   -3.8979    5.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -5.2583    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322   -5.4197    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869   -2.1634   -2.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    1.3011   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    3.5131   -1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872    3.9561   -3.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192    1.2174   -3.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832   -0.2755   -2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 26  1  0
 12 11  2  0
 26 28  2  0
 28 21  1  0
 11 30  1  0
 12 13  1  0
 30 29  1  0
 11 10  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 26 27  1  0
 19 20  2  0
 24 25  1  0
 20 29  1  0
 10  9  1  0
 30 16  2  0
  9  7  2  0
 20 21  1  0
  7  6  1  0
 15 14  2  0
  6  5  1  0
 21 22  2  0
  5  4  1  0
 16 15  1  0
  4  2  2  3
 22 23  1  0
  2  1  1  0
 14 12  1  0
  2  3  1  0
 23 24  2  0
  7  8  1  0
 15 50  1  0
 14 49  1  0
 19 51  1  0
 22 52  1  0
 23 53  1  0
 28 56  1  0
 13 48  1  0
 10 46  1  0
 10 47  1  0
 27 55  1  0
 25 54  1  0
  9 45  1  0
  6 40  1  0
  6 41  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 42  1  0
  8 43  1  0
  8 44  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.398  -3.363   2.189  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.440  -1.857   2.178  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.347  -1.251   0.807  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.544  -1.168   3.331  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.598   0.326   3.526  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.444   0.857   4.391  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.927   0.714   3.751  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.213   1.680   2.634  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.782  -0.230   4.197  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.159  -0.569   3.694  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.186  -1.919   3.008  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.419  -3.096   3.736  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.660  -3.006   5.079  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.406  -4.350   3.122  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.148  -4.446   1.756  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.906  -3.286   1.017  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.624  -3.371  -0.424  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.583  -4.438  -1.023  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.381  -2.103  -1.127  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.416  -0.959  -0.431  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.169   0.345  -1.072  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.026   1.428  -0.802  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.802   2.681  -1.377  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.715   2.852  -2.220  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.493   4.076  -2.781  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.853   1.794  -2.493  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.204   2.037  -3.327  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.069   0.542  -1.925  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.690  -0.876   0.923  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.924  -2.032   1.630  0.00  0.00           C+0
HETATM   31  H   UNK     0       0.458  -3.720   1.756  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.474  -3.775   3.201  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.229  -3.770   1.602  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.221  -0.167   0.814  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.250  -1.480   0.233  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.488  -1.667   0.271  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.599  -1.732   4.262  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.542   0.554   4.039  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.638   0.870   2.579  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.465   0.352   5.367  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.620   1.918   4.610  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.251   1.658   2.298  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.579   1.464   1.770  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.011   2.706   2.962  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.457  -0.869   5.019  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.851  -0.567   4.546  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.564   0.195   3.024  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.787  -3.898   5.442  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.589  -5.258   3.689  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.132  -5.420   1.271  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.187  -2.163  -2.189  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.879   1.301  -0.137  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.466   3.513  -1.167  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.687   3.956  -3.322  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.719   1.217  -3.418  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.383  -0.276  -2.126  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   34   35   36                                             
CONECT    4    5    2   37                                                  
CONECT    5    6    4   38   39                                             
CONECT    6    7    5   40   41                                             
CONECT    7    9    6    8                                                  
CONECT    8    7   42   43   44                                             
CONECT    9   10    7   45                                                  
CONECT   10   11    9   46   47                                             
CONECT   11   12   30   10                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   48                                                       
CONECT   14   15   12   49                                                  
CONECT   15   14   16   50                                                  
CONECT   16   17   30   15                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   51                                                  
CONECT   20   19   29   21                                                  
CONECT   21   28   20   22                                                  
CONECT   22   21   23   52                                                  
CONECT   23   22   24   53                                                  
CONECT   24   26   25   23                                                  
CONECT   25   24   54                                                       
CONECT   26   24   28   27                                                  
CONECT   27   26   55                                                       
CONECT   28   26   21   56                                                  
CONECT   29   30   20                                                       
CONECT   30   11   29   16                                                  
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   19                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   25                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
    1.3983   -3.3634    2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4403   -1.8572    2.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465   -1.2506    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436   -1.1680    3.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984    0.3258    3.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436    0.8568    4.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    0.7144    3.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131    1.6804    2.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -0.2295    4.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1591   -0.5692    3.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1861   -1.9189    3.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -3.0965    3.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604   -3.0058    5.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4059   -4.3504    3.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478   -4.4461    1.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9063   -3.2856    1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -3.3712   -0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832   -4.4380   -1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -2.1031   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162   -0.9590   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1693    0.3454   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    1.4279   -0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016    2.6808   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152    2.8515   -2.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931    4.0757   -2.7809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526    1.7938   -2.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2041    2.0374   -3.3267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689    0.5418   -1.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6898   -0.8759    0.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9237   -2.0319    1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -3.7197    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4736   -3.7751    3.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2287   -3.7696    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -0.1666    0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -1.4805    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4884   -1.6674    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5986   -1.7324    4.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    0.5541    4.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379    0.8703    2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    0.3524    5.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9178    4.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510    1.6582    2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5785    1.4642    1.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108    2.7056    2.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571   -0.8691    5.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -0.5674    4.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5638    0.1945    3.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7873   -3.8979    5.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -5.2583    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322   -5.4197    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869   -2.1634   -2.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    1.3011   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    3.5131   -1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872    3.9561   -3.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192    1.2174   -3.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832   -0.2755   -2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 26  1  0
 12 11  2  0
 26 28  2  0
 28 21  1  0
 11 30  1  0
 12 13  1  0
 30 29  1  0
 11 10  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 26 27  1  0
 19 20  2  0
 24 25  1  0
 20 29  1  0
 10  9  1  0
 30 16  2  0
  9  7  2  0
 20 21  1  0
  7  6  1  0
 15 14  2  0
  6  5  1  0
 21 22  2  0
  5  4  1  0
 16 15  1  0
  4  2  2  3
 22 23  1  0
  2  1  1  0
 14 12  1  0
  2  3  1  0
 23 24  2  0
  7  8  1  0
 15 50  1  0
 14 49  1  0
 19 51  1  0
 22 52  1  0
 23 53  1  0
 28 56  1  0
 13 48  1  0
 10 46  1  0
 10 47  1  0
 27 55  1  0
 25 54  1  0
  9 45  1  0
  6 40  1  0
  6 41  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 42  1  0
  8 43  1  0
  8 44  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₅

Average Mass

406.4780 Da

Monoisotopic Mass

406.17802 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-8-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxychromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1O[H])C1=C([H])C(=O)C2=C(O1)C(=C(O[H])C([H])=C2[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H26O5/c1-15(2)5-4-6-16(3)7-9-18-20(26)12-10-19-22(28)14-24(30-25(18)19)17-8-11-21(27)23(29)13-17/h5,7-8,10-14,26-27,29H,4,6,9H2,1-3H3/b16-7+

InChI Key

SWGONUIXZUDUSG-FRKPEAEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃ + CD₃OD ( 10 : 1 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artocarpus nobilis	LOTUS Database	35616633
Matricaria chamomilla	JEOL database	Jayasinghe, L., et al, Phytochemistry 67, 1353 (2006)

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

8-prenylated flavone
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
1-benzopyran
Monoterpenoid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	5.31	ALOGPS
logP	5.44	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	6.31	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.96 m³·mol⁻¹	ChemAxon
Polarizability	43.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

17240403

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16081691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jayasinghe, L., et al. (2006). Jayasinghe, L., et al, Phytochemistry 67, 1353 (2006). Phytochem..

Showing NP-Card for 8-geranyl-3',4',7-trihydroxyflavone (NP0032216)

MOL for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

3D MOL for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

3D SDF for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

3D-SDF for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

PDB for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

3D PDB for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

SMILES for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

INCHI for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

Structure for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)

3D Structure for NP0032216 (8-geranyl-3',4',7-trihydroxyflavone)