NP-MRD: Showing NP-Card for Pennicitrinone C (NP0007577)

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Record Information

Version

2.0

Created at

2020-12-09 04:25:18 UTC

Updated at

2021-07-15 16:57:58 UTC

NP-MRD ID

NP0007577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pennicitrinone C

Provided By

NPAtlas

Description

Pennicitrinone C is found in Penicillium and Penicillium citrinum. Pennicitrinone C was first documented in 2008 (PMID: 18281952). Based on a literature review very few articles have been published on pennicitrinone C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118413D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242118413D          

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    6.8692    0.2931    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2124    2.2244   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    2.0734    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742    3.0547    2.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1764    0.8734    1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    2.4420    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9021    2.4069    1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662   -2.7065   -2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -2.0430    0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -1.8339   -2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1380   -3.2626   -1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8248   -2.7893   -1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    0.2806   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8948    0.5998   -1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0044   -0.9727   -0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5492   -0.9666   -1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23  2  1  0  0  0  0
 22 11  1  0  0  0  0
 20 13  1  0  0  0  0
 28 19  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  4 33  1  1  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  6  0  0  0
  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  8 41  1  0  0  0  0
 10 42  1  0  0  0  0
 14 43  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
 24 47  1  0  0  0  0
 26 48  1  1  0  0  0
 27 49  1  0  0  0  0
 27 50  1  0  0  0  0
 27 51  1  0  0  0  0
 28 52  1  6  0  0  0
 29 53  1  0  0  0  0
 29 54  1  0  0  0  0
 29 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2OC3=C([H])C(=O)C(=C4C3=C(O[C@]([H])(C([H])([H])[H])[C@@]4([H])C([H])([H])[H])C2=C(O[H])C(=C1[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O6/c1-8(12(5)24)17-11(4)20(26)19-22-18-15(29-23(19)21(17)27)7-14(25)10(3)16(18)9(2)13(6)28-22/h7-9,12-13,24,26-27H,1-6H3/t8-,9-,12+,13-/m1/s1

> <INCHI_KEY>
HESPWWKIRCFDQL-MNUQUWEESA-N

> <FORMULA>
C23H26O6

> <MOLECULAR_WEIGHT>
398.455

> <EXACT_MASS>
398.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.946079817863264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(14S,15R)-3,6-dihydroxy-5-[(2S,3S)-3-hydroxybutan-2-yl]-4,12,14,15-tetramethyl-8,16-dioxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,9,12-hexaen-11-one

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.7411372070000013

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.14321823313118

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.73898106627753

> <JCHEM_PKA_STRONGEST_BASIC>
2.074465581526866

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
112.5285

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(14S,15R)-3,6-dihydroxy-5-[(2S,3S)-3-hydroxybutan-2-yl]-4,12,14,15-tetramethyl-8,16-dioxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,9,12-hexaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    3.0088   -2.1827   -1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -1.2157   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -0.3320    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100   -0.3855    0.5182 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7928    0.3113    1.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9427    0.3323   -0.6942 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4433    0.3257   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5496    1.6841   -0.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0470    0.5473    1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    1.4270    1.9802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684    0.5649    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529    1.4129    1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3520    1.5100    1.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    2.4108    2.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4256    2.4374    1.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883    3.2872    2.6269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    1.6145    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5975    1.7669    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214    0.6815    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342    0.6111    0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600   -0.2916   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -0.3099   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8764   -1.1913   -0.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -2.0411   -1.6570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270   -1.1349   -1.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2691   -1.5291   -0.7266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8394   -2.4041   -1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978   -0.1897   -0.7032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4460   -0.3395   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0393   -2.3753   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4775   -3.1825   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229   -1.9663   -2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -1.4207    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8306   -0.0659    2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1509    0.0108    2.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471    1.4028    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158   -0.1383   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8253    1.2504   -1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -0.5663   -1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8692    0.2931    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2124    2.2244   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    2.0734    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742    3.0547    2.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1764    0.8734    1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    2.4420    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9021    2.4069    1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662   -2.7065   -2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -2.0430    0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -1.8339   -2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1380   -3.2626   -1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8248   -2.7893   -1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    0.2806   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8948    0.5998   -1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0044   -0.9727   -0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5492   -0.9666   -1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  3  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 23  2  1  0
 22 11  1  0
 20 13  1  0
 28 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
 10 42  1  0
 14 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 24 47  1  0
 26 48  1  1
 27 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  6
 29 53  1  0
 29 54  1  0
 29 55  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.009  -2.183  -1.339  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.256  -1.216  -0.555  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.832  -0.332   0.370  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.310  -0.386   0.518  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.793   0.311   1.769  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.943   0.332  -0.694  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.443   0.326  -0.650  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.550   1.684  -0.680  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.047   0.547   1.069  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.590   1.427   1.980  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.668   0.565   0.862  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.053   1.413   1.539  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.352   1.510   1.415  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.094   2.411   2.138  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.426   2.437   1.939  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.088   3.287   2.627  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.114   1.615   1.049  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.598   1.767   0.929  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.421   0.682   0.288  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.034   0.611   0.458  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.260  -0.292  -0.259  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.085  -0.310  -0.056  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.876  -1.191  -0.756  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.254  -2.041  -1.657  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.927  -1.135  -1.147  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.269  -1.529  -0.727  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.839  -2.404  -1.783  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.998  -0.190  -0.703  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.446  -0.340  -0.896  0.00  0.00           C+0
HETATM   30  H   UNK     0       4.039  -2.375  -1.082  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.478  -3.183  -1.246  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.923  -1.966  -2.447  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.699  -1.421   0.488  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.831  -0.066   2.010  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.151   0.011   2.648  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.847   1.403   1.701  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.616  -0.138  -1.640  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.825   1.250  -1.146  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.787  -0.566  -1.258  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.869   0.293   0.364  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.212   2.224  -0.178  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.017   2.073   2.491  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.574   3.055   2.830  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.176   0.873   1.098  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.899   2.442   0.108  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.902   2.407   1.840  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.766  -2.707  -2.222  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.242  -2.043   0.228  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.941  -1.834  -2.720  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.138  -3.263  -1.912  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.825  -2.789  -1.436  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.652   0.281  -1.703  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.895   0.600  -1.218  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.004  -0.973  -0.205  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.549  -0.967  -1.872  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   23                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6   33                                             
CONECT    5    4   34   35   36                                             
CONECT    6    4    7    8   37                                             
CONECT    7    6   38   39   40                                             
CONECT    8    6   41                                                       
CONECT    9    3   10   11                                                  
CONECT   10    9   42                                                       
CONECT   11    9   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   43                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17   44   45   46                                             
CONECT   19   17   20   28                                                  
CONECT   20   19   21   13                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   11                                                  
CONECT   23   22   24    2                                                  
CONECT   24   23   47                                                       
CONECT   25   21   26                                                       
CONECT   26   25   27   28   48                                             
CONECT   27   26   49   50   51                                             
CONECT   28   26   29   19   52                                             
CONECT   29   28   53   54   55                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42   10                                                            
CONECT   43   14                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   24                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
CONECT   51   27                                                            
CONECT   52   28                                                            
CONECT   53   29                                                            
CONECT   54   29                                                            
CONECT   55   29                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
    3.0088   -2.1827   -1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -1.2157   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -0.3320    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100   -0.3855    0.5182 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7928    0.3113    1.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9427    0.3323   -0.6942 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4433    0.3257   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5496    1.6841   -0.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0470    0.5473    1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    1.4270    1.9802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684    0.5649    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529    1.4129    1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3520    1.5100    1.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    2.4108    2.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4256    2.4374    1.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883    3.2872    2.6269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    1.6145    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5975    1.7669    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214    0.6815    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342    0.6111    0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600   -0.2916   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -0.3099   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8764   -1.1913   -0.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -2.0411   -1.6570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270   -1.1349   -1.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2691   -1.5291   -0.7266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8394   -2.4041   -1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978   -0.1897   -0.7032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4460   -0.3395   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0393   -2.3753   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4775   -3.1825   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229   -1.9663   -2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -1.4207    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8306   -0.0659    2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1509    0.0108    2.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471    1.4028    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158   -0.1383   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8253    1.2504   -1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -0.5663   -1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8692    0.2931    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2124    2.2244   -0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    2.0734    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742    3.0547    2.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1764    0.8734    1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    2.4420    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9021    2.4069    1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662   -2.7065   -2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -2.0430    0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -1.8339   -2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1380   -3.2626   -1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8248   -2.7893   -1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    0.2806   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8948    0.5998   -1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0044   -0.9727   -0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5492   -0.9666   -1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  3  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 23  2  1  0
 22 11  1  0
 20 13  1  0
 28 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
 10 42  1  0
 14 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 24 47  1  0
 26 48  1  1
 27 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  6
 29 53  1  0
 29 54  1  0
 29 55  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₆

Average Mass

398.4550 Da

Monoisotopic Mass

398.17294 Da

IUPAC Name

(14S,15R)-3,6-dihydroxy-5-[(2S,3S)-3-hydroxybutan-2-yl]-4,12,14,15-tetramethyl-8,16-dioxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,9,12-hexaen-11-one

Traditional Name

(14S,15R)-3,6-dihydroxy-5-[(2S,3S)-3-hydroxybutan-2-yl]-4,12,14,15-tetramethyl-8,16-dioxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,9,12-hexaen-11-one

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@@H](C)C1=C(O)C2=C(C(O)=C1C)C1=C3C(O2)=CC(=O)C(C)=C3[C@H](C)[C@@H](C)O1

InChI Identifier

InChI=1S/C23H26O6/c1-8(12(5)24)17-11(4)20(26)19-22-18-15(29-23(19)21(17)27)7-14(25)10(3)16(18)9(2)13(6)28-22/h7-9,12-13,24,26-27H,1-6H3/t8-,9-,12+,13-/m1/s1

InChI Key

HESPWWKIRCFDQL-MNUQUWEESA-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
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
Penicillium	NPAtlas	18281952
Penicillium citrinum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Penicillium citrinum B-57u	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	3.29	ALOGPS
logP	2.74	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	6.74	ChemAxon
pKa (Strongest Basic)	2.07	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	112.53 m³·mol⁻¹	ChemAxon
Polarizability	43.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA007100

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039943

Chemspider ID

23340845

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24850196

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lu ZY, Lin ZJ, Wang WL, Du L, Zhu TJ, Fang YC, Gu QQ, Zhu WM: Citrinin dimers from the halotolerant fungus Penicillium citrinum B-57. J Nat Prod. 2008 Apr;71(4):543-6. doi: 10.1021/np0704708. Epub 2008 Feb 19. [PubMed:18281952 ]

Showing NP-Card for Pennicitrinone C (NP0007577)

MOL for NP0007577 (Pennicitrinone C)

3D MOL for NP0007577 (Pennicitrinone C)

3D SDF for NP0007577 (Pennicitrinone C)

3D-SDF for NP0007577 (Pennicitrinone C)

PDB for NP0007577 (Pennicitrinone C)

3D PDB for NP0007577 (Pennicitrinone C)

SMILES for NP0007577 (Pennicitrinone C)

INCHI for NP0007577 (Pennicitrinone C)

Structure for NP0007577 (Pennicitrinone C)

3D Structure for NP0007577 (Pennicitrinone C)