NP-MRD: Showing NP-Card for grifolin (NP0029010)

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Record Information

Version

2.0

Created at

2021-06-19 20:44:35 UTC

Updated at

2021-06-29 23:56:07 UTC

NP-MRD ID

NP0029010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

grifolin

Provided By

JEOL Database JEOL Logo

Description

Grifolin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. grifolin is found in Albatrellus flettii, Albatrellus caeruleoporus, Albatrellus dispansus, Albatrellus ovinus, Albatrellus pes-caprae, Baorangia pseudocalopus, Grifolia confluens, Peperomia galioides and Phellodon niger. grifolin was first documented in 2017 (PMID: 29071135). Based on a literature review a significant number of articles have been published on Grifolin (PMID: 34100599) (PMID: 33402084) (PMID: 32972142) (PMID: 32369483) (PMID: 31791817) (PMID: 29843779).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122443D          

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M  END

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  Mrv1652306192122443D          

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    4.0607   -1.3672   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6721    0.2525   -2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.0269   -2.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443   -2.2345   -3.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -2.0842   -3.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9532   -2.8480   -0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465   -3.9509   -2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -3.1021   -1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4093   -2.5250   -2.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -4.1836   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5982   -1.8465    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304   -2.3724    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -1.9687    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754   -0.3491    4.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.7931    3.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562    4.0419    3.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026    4.3171    2.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    4.4985    1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    2.8066   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7690   -0.4236   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 17 19  2  0  0  0  0
  9  7  2  0  0  0  0
 19 20  1  0  0  0  0
  7  6  1  0  0  0  0
 16 15  1  0  0  0  0
  6  5  1  0  0  0  0
 22 23  1  0  0  0  0
  5  4  1  0  0  0  0
 15 14  1  0  0  0  0
  4  2  2  3  0  0  0
  2  1  1  0  0  0  0
 14 12  2  0  0  0  0
 17 18  1  0  0  0  0
 23 16  2  0  0  0  0
 23 24  1  0  0  0  0
 12 11  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  2  3  1  0  0  0  0
 11 10  1  0  0  0  0
  7  8  1  0  0  0  0
 16 17  1  0  0  0  0
 12 13  1  0  0  0  0
 19 51  1  0  0  0  0
 22 55  1  0  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 14 47  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
  9 39  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  4 31  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 18 50  1  0  0  0  0
 24 56  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 21 54  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C(O[H])=C1C([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])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+

> <INCHI_KEY>
PZHNKNRPGLTZPO-VZRGJMDUSA-N

> <FORMULA>
C22H32O2

> <MOLECULAR_WEIGHT>
328.4883

> <EXACT_MASS>
328.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.43695367631263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

> <ALOGPS_LOGP>
6.69

> <JCHEM_LOGP>
6.927532111333333

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.647277968375189

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.19301081602902

> <JCHEM_PKA_STRONGEST_BASIC>
-5.715809105897486

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
106.90899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
    4.1193    3.9994    1.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6808    4.2275    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    5.6177    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693    3.3080    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1829    1.8728    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3414    1.6700   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595    0.2140   -1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9485   -0.3112   -1.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421   -0.5116   -2.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613   -1.9586   -2.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1895   -2.9187   -1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -2.6843   -1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389   -3.1432   -1.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156   -2.1135    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5684   -1.7434    0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -0.2752    1.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021    0.1411    2.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610   -0.7980    3.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    1.4897    2.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967    2.4642    2.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196    3.9136    2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    2.0688    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.7214    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    0.4464   -0.9745 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7519    4.7693    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2391    4.0534    2.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072    3.0345    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    5.8348    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285    5.7485    0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663    6.3572    0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8458    3.5960    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738    1.5254    0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576    1.2533    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511    2.0583   -2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828    2.2663   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2198   -0.2098   -0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607   -1.3672   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6721    0.2525   -2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.0269   -2.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443   -2.2345   -3.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -2.0842   -3.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9532   -2.8480   -0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465   -3.9509   -2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -3.1021   -1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4093   -2.5250   -2.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -4.1836   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5982   -1.8465    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304   -2.3724    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -1.9687    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754   -0.3491    4.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.7931    3.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562    4.0419    3.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026    4.3171    2.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    4.4985    1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    2.8066   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7690   -0.4236   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 17 19  2  0
  9  7  2  0
 19 20  1  0
  7  6  1  0
 16 15  1  0
  6  5  1  0
 22 23  1  0
  5  4  1  0
 15 14  1  0
  4  2  2  3
  2  1  1  0
 14 12  2  0
 17 18  1  0
 23 16  2  0
 23 24  1  0
 12 11  1  0
 20 21  1  0
 20 22  2  0
  2  3  1  0
 11 10  1  0
  7  8  1  0
 16 17  1  0
 12 13  1  0
 19 51  1  0
 22 55  1  0
 15 48  1  0
 15 49  1  0
 14 47  1  0
 11 42  1  0
 11 43  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  0
  6 34  1  0
  6 35  1  0
  5 32  1  0
  5 33  1  0
  4 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 18 50  1  0
 24 56  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       4.119   3.999   1.282  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.681   4.228   0.909  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.178   5.618   1.198  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.869   3.308   0.351  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.183   1.873   0.022  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.341   1.670  -1.489  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.559   0.214  -1.861  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.949  -0.311  -1.620  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.542  -0.512  -2.366  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.561  -1.959  -2.782  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.190  -2.919  -1.641  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.195  -2.684  -1.055  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.339  -3.143  -1.917  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.316  -2.114   0.162  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.568  -1.743   0.911  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.595  -0.275   1.281  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.302   0.141   2.587  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.961  -0.798   3.523  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.345   1.490   2.954  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.697   2.464   2.015  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.720   3.914   2.397  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.966   2.069   0.702  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.904   0.721   0.343  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.152   0.446  -0.975  0.00  0.00           O+0
HETATM   25  H   UNK     0       4.752   4.769   0.827  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.239   4.053   2.369  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.507   3.034   0.948  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.261   5.835   2.268  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.129   5.749   0.914  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.766   6.357   0.645  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.846   3.596   0.110  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.074   1.525   0.553  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.358   1.253   0.396  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.451   2.058  -2.003  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.183   2.266  -1.866  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.220  -0.210  -0.564  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.061  -1.367  -1.877  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.672   0.253  -2.218  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.573  -0.027  -2.483  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.544  -2.235  -3.179  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.867  -2.084  -3.622  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.953  -2.848  -0.855  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.246  -3.951  -2.010  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.305  -3.102  -1.411  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.409  -2.525  -2.817  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.187  -4.184  -2.223  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.598  -1.847   0.696  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.630  -2.372   1.807  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.479  -1.969   0.348  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.775  -0.349   4.364  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.110   1.793   3.971  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.156   4.042   3.393  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.703   4.317   2.400  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.326   4.498   1.698  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.215   2.807  -0.057  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.769  -0.424  -1.176  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   28   29   30                                             
CONECT    4    5    2   31                                                  
CONECT    5    6    4   32   33                                             
CONECT    6    7    5   34   35                                             
CONECT    7    9    6    8                                                  
CONECT    8    7   36   37   38                                             
CONECT    9   10    7   39                                                  
CONECT   10    9   11   40   41                                             
CONECT   11   12   10   42   43                                             
CONECT   12   14   11   13                                                  
CONECT   13   12   44   45   46                                             
CONECT   14   15   12   47                                                  
CONECT   15   16   14   48   49                                             
CONECT   16   15   23   17                                                  
CONECT   17   19   18   16                                                  
CONECT   18   17   50                                                       
CONECT   19   17   20   51                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   52   53   54                                             
CONECT   22   23   20   55                                                  
CONECT   23   22   16   24                                                  
CONECT   24   23   56                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    6                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   24                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  112    0
END

RDKit          3D

56 56  0  0  0  0  0  0  0  0999 V2000
    4.1193    3.9994    1.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6808    4.2275    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    5.6177    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693    3.3080    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1829    1.8728    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3414    1.6700   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595    0.2140   -1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9485   -0.3112   -1.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421   -0.5116   -2.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613   -1.9586   -2.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1895   -2.9187   -1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -2.6843   -1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389   -3.1432   -1.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156   -2.1135    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5684   -1.7434    0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -0.2752    1.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021    0.1411    2.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610   -0.7980    3.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    1.4897    2.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967    2.4642    2.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196    3.9136    2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    2.0688    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.7214    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    0.4464   -0.9745 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7519    4.7693    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2391    4.0534    2.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072    3.0345    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    5.8348    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285    5.7485    0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663    6.3572    0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8458    3.5960    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738    1.5254    0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576    1.2533    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511    2.0583   -2.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828    2.2663   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2198   -0.2098   -0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607   -1.3672   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6721    0.2525   -2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.0269   -2.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443   -2.2345   -3.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -2.0842   -3.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9532   -2.8480   -0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465   -3.9509   -2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -3.1021   -1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4093   -2.5250   -2.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -4.1836   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5982   -1.8465    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304   -2.3724    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -1.9687    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7754   -0.3491    4.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.7931    3.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562    4.0419    3.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026    4.3171    2.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    4.4985    1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    2.8066   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7690   -0.4236   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 17 19  2  0
  9  7  2  0
 19 20  1  0
  7  6  1  0
 16 15  1  0
  6  5  1  0
 22 23  1  0
  5  4  1  0
 15 14  1  0
  4  2  2  3
  2  1  1  0
 14 12  2  0
 17 18  1  0
 23 16  2  0
 23 24  1  0
 12 11  1  0
 20 21  1  0
 20 22  2  0
  2  3  1  0
 11 10  1  0
  7  8  1  0
 16 17  1  0
 12 13  1  0
 19 51  1  0
 22 55  1  0
 15 48  1  0
 15 49  1  0
 14 47  1  0
 11 42  1  0
 11 43  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  0
  6 34  1  0
  6 35  1  0
  5 32  1  0
  5 33  1  0
  4 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 18 50  1  0
 24 56  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
3,8,12-Trimethyl-5,7,11-tridecatriene-3,4-diol	HMDB
2-Farnesyl-5-methylresorcinol	HMDB
5-Methyl-2-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol, 9ci	HMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenol	HMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenoxide	HMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenoxide (8ci)	HMDB
e,e,5-Methyl-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol	HMDB
Hexadecyltrimethylammonium pentachlorophenol	HMDB
Hexadecyltrimethylammonium pentachlorophenoxide (6ci,7ci)	HMDB
Trimethylcetylammonium pentachlorophenate	HMDB
Grifolin	MeSH

Chemical Formula

C₂₂H₃₂O₂

Average Mass

328.4883 Da

Monoisotopic Mass

328.24023 Da

IUPAC Name

5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

Traditional Name

5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C(O[H])=C1C([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])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+

InChI Key

PZHNKNRPGLTZPO-VZRGJMDUSA-N

Experimental Spectra

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

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Albatrellopsis flettii	LOTUS Database	35616633
Albatrellus caeruleoporus	LOTUS Database	35616633
Albatrellus dispansus	LOTUS Database	35616633
Albatrellus ovinus	JEOL database	Nukata, M., et al, Phytochemistry 59, 731 (2002),Ishii, N., et al, Chem. +
Albatrellus pes-caprae	LOTUS Database	35616633
Baorangia pseudocalopus	LOTUS Database	35616633
Grifolia confluens	-	KNApSAcK
Peperomia galioides	LOTUS Database	35616633
Phellodon niger	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Rhododendron dauricum	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Albatrellus confluens	KNApSAcK Database	22123792
Grifola confluens	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic 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	6.69	ALOGPS
logP	6.93	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.91 m³·mol⁻¹	ChemAxon
Polarizability	40.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030446

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002311

KNApSAcK ID

C00023937

Chemspider ID

4522608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Grifolin

METLIN ID

Not Available

PubChem Compound

5372312

PDB ID

Not Available

ChEBI ID

544843

Good Scents ID

rw1820021

References

General References

Masuda Y, Fujihara K, Hayashi S, Sasaki H, Kino Y, Kamauchi H, Noji M, Satoh JI, Takanami T, Kinoshita K, Koyama K: Inhibition of BACE1 and Amyloid-beta Aggregation by Meroterpenoids from the Mushroom Albatrellus yasudae. J Nat Prod. 2021 Jun 25;84(6):1748-1754. doi: 10.1021/acs.jnatprod.0c01329. Epub 2021 Jun 8. [PubMed:34100599 ]
Huang DN, Wang S, Sooranna SR, Miao JH: The efficacy of natural bioactive compounds for the treatment of nasopharyngeal carcinoma. Mini Rev Med Chem. 2021 Jan 4. pii: MRMC-EPUB-113051. doi: 10.2174/1389557521666210105113831. [PubMed:33402084 ]
Jentsch NG, Zhang X, Magolan J: Efficient Synthesis of Cannabigerol, Grifolin, and Piperogalin via Alumina-Promoted Allylation. J Nat Prod. 2020 Sep 25;83(9):2587-2591. doi: 10.1021/acs.jnatprod.0c00131. Epub 2020 Sep 10. [PubMed:32972142 ]
Yaqoob A, Li WM, Liu V, Wang C, Mackedenski S, Tackaberry LE, Massicotte HB, Egger KN, Reimer K, Lee CH: Grifolin, neogrifolin and confluentin from the terricolous polypore Albatrellus flettii suppress KRAS expression in human colon cancer cells. PLoS One. 2020 May 5;15(5):e0231948. doi: 10.1371/journal.pone.0231948. eCollection 2020. [PubMed:32369483 ]
Akiba M, Kinoshita K, Kino Y, Sato JI, Koyama K: Isolation of three new meroterpenoids and seven known compounds from Albatrellus yasudae and their Abeta-aggregation inhibitory activity. Bioorg Med Chem Lett. 2020 Jan 15;30(2):126808. doi: 10.1016/j.bmcl.2019.126808. Epub 2019 Nov 21. [PubMed:31791817 ]
Zhao Y, Zhang L, Yan A, Chen D, Xie R, Liu Y, Liang X, Zhao Y, Wei L, Yu J, Xu X, Su X: Grifolic acid induces GH3 adenoma cell death by inhibiting ATP production through a GPR120-independent mechanism. BMC Pharmacol Toxicol. 2018 May 30;19(1):26. doi: 10.1186/s40360-018-0215-4. [PubMed:29843779 ]
Luo X, Hong L, Cheng C, Li N, Zhao X, Shi F, Liu J, Fan J, Zhou J, Bode AM, Cao Y: DNMT1 mediates metabolic reprogramming induced by Epstein-Barr virus latent membrane protein 1 and reversed by grifolin in nasopharyngeal carcinoma. Cell Death Dis. 2018 May 23;9(6):619. doi: 10.1038/s41419-018-0662-2. [PubMed:29795311 ]
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Nukata, M., et al. (2002). Nukata, M., et al, Phytochemistry 59, 731 (2002),Ishii, N., et al, Chem. +. Phytochem..

Showing NP-Card for grifolin (NP0029010)

MOL for NP0029010 (grifolin)

3D MOL for NP0029010 (grifolin)

3D SDF for NP0029010 (grifolin)

3D-SDF for NP0029010 (grifolin)

PDB for NP0029010 (grifolin)

3D PDB for NP0029010 (grifolin)

SMILES for NP0029010 (grifolin)

INCHI for NP0029010 (grifolin)

Structure for NP0029010 (grifolin)

3D Structure for NP0029010 (grifolin)