NP-MRD: Showing NP-Card for Pitholide D (NP0084352)

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Record Information

Version

2.0

Created at

2022-04-29 05:06:25 UTC

Updated at

2022-04-29 05:06:25 UTC

NP-MRD ID

NP0084352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pitholide D

Description

Pitholide D belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Pitholide D is found in Pithomyces sp. Pitholide D was first documented in 2019 (PMID: 31729648). Based on a literature review very few articles have been published on Pitholide D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207062D          

 26 28  0  0  1  0            999 V2000
    0.8608   -1.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2477   -1.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484   -3.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6746   -3.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816   -3.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7985   -5.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -4.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8406   -3.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337   -3.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -2.5516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3307   -1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717   -2.3800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4567   -1.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592   -1.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 12  2  0  0  0  0
  3 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    7.3483    0.1788    1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9756   -0.1680    2.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -0.4300    1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9894    0.8056    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904    0.5863   -0.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798    0.2424   -0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8235    0.0323   -1.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401   -0.3040   -1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1395   -1.4941   -1.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055    0.7253   -1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523    0.4667   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701   -0.7840   -0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7138   -0.7120    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4812   -1.8790    0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6238   -1.7890    1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4148   -2.9770    1.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0699   -0.4994    1.4305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838    0.6508    1.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2307    0.5950    0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5899    1.8839    0.0497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9200    2.4398    1.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6076    1.7274   -1.0848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4053    1.7059   -2.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6745    2.7213   -1.2381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    2.1632   -1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246    2.7876   -1.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0824   -0.0239    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3717    1.2318    1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5423   -0.4647    0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5283    0.6647    2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0328   -1.0680    2.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750   -0.7102    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4145   -1.2655    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6897    1.7047    0.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0097    1.0136   -0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5474   -0.2080   -1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784    1.5160   -1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685    1.0682    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6341   -0.6881    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.9669   -2.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726   -0.7935   -2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685   -1.7382   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1089   -2.8646    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2262   -3.2162    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765   -3.8794    1.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9381   -2.7483    2.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8267    1.6151    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    2.5809   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9468    3.4436    1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0926    0.8631   -2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6425    1.7201   -3.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984    2.7069   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 10  1  0
 22 11  1  0
 19 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
 12 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 18 47  1  0
 20 48  1  6
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
M  END


  Mrv1652304292207062D          

 26 28  0  0  1  0            999 V2000
    0.8608   -1.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2477   -1.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484   -3.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6746   -3.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816   -3.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7985   -5.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -4.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8406   -3.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337   -3.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -2.5516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3307   -1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717   -2.3800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4567   -1.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5592   -1.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 12  2  0  0  0  0
  3 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)C1=C2C=C3C=C(C)OC=C3[C@@H](O)[C@@]2(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O5/c1-4-5-6-7-8-9-17(22)18-16-11-14-10-13(2)25-12-15(14)19(23)21(16,3)26-20(18)24/h10-12,19,23H,4-9H2,1-3H3/t19-,21+/m1/s1

> <INCHI_KEY>
LWWKRRPNDFSENZ-CTNGQTDRSA-N

> <FORMULA>
C21H26O5

> <MOLECULAR_WEIGHT>
358.434

> <EXACT_MASS>
358.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.18616281365494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R,9aS)-9-hydroxy-6,9a-dimethyl-3-octanoyl-2H,9H,9aH-furo[3,2-g]isochromen-2-one

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
2.8557587039999994

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.40010472441357

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.182461932589352

> <JCHEM_PKA_STRONGEST_BASIC>
-3.593791031948969

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
101.00819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,9aS)-9-hydroxy-6,9a-dimethyl-3-octanoyl-9H-furo[3,2-g]isochromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       1.607  -2.399   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.462  -3.429   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.623  -4.961   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.957  -5.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.291  -4.961   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.624  -5.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.958  -4.961   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.292  -5.731   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.625  -4.961   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.959  -5.731   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.293  -4.961   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.957  -7.271   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.783  -5.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.259  -7.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.766  -7.372   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.242  -8.837   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.748  -9.157   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.224 -10.621   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.778  -8.012   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.302  -6.548   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.796  -6.228   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.320  -4.763   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.351  -3.618   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.814  -4.443   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.719  -3.197   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.044  -3.109   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    4                                                            
CONECT   13    3   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   13   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    2                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₅

Average Mass

358.4340 Da

Monoisotopic Mass

358.17802 Da

IUPAC Name

(9R,9aS)-9-hydroxy-6,9a-dimethyl-3-octanoyl-2H,9H,9aH-furo[3,2-g]isochromen-2-one

Traditional Name

(9R,9aS)-9-hydroxy-6,9a-dimethyl-3-octanoyl-9H-furo[3,2-g]isochromen-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)C1=C2C=C3C=C(C)OC=C3[C@@H](O)[C@@]2(C)OC1=O

InChI Identifier

InChI=1S/C21H26O5/c1-4-5-6-7-8-9-17(22)18-16-11-14-10-13(2)25-12-15(14)19(23)21(16,3)26-20(18)24/h10-12,19,23H,4-9H2,1-3H3/t19-,21+/m1/s1

InChI Key

LWWKRRPNDFSENZ-CTNGQTDRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pithomyces sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.56	ALOGPS
logP	2.86	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	101.01 m³·mol⁻¹	ChemAxon
Polarizability	40.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00053693

Chemspider ID

10476919

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21774811

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nalin Rathnayake GR, Savitri Kumar N, Jayasinghe L, Araya H, Fujimoto Y: Secondary Metabolites Produced by an Endophytic Fungus Pestalotiopsis microspora. Nat Prod Bioprospect. 2019 Dec;9(6):411-417. doi: 10.1007/s13659-019-00225-0. Epub 2019 Nov 15. [PubMed:31729648 ]

Showing NP-Card for Pitholide D (NP0084352)

MOL for NP0084352 (Pitholide D)

3D MOL for NP0084352 (Pitholide D)

3D SDF for NP0084352 (Pitholide D)

3D-SDF for NP0084352 (Pitholide D)

PDB for NP0084352 (Pitholide D)

3D PDB for NP0084352 (Pitholide D)

SMILES for NP0084352 (Pitholide D)

INCHI for NP0084352 (Pitholide D)

Structure for NP0084352 (Pitholide D)

3D Structure for NP0084352 (Pitholide D)