NP-MRD: Showing NP-Card for Pinusolidic acid (NP0141171)

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Record Information

Version

1.0

Created at

2022-06-29 22:14:33 UTC

Updated at

2022-06-29 22:14:33 UTC

NP-MRD ID

NP0141171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pinusolidic acid

Description

Pinusolidic acid, also known as pinusolidate, belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Pinusolidic acid is found in Agathis macrophylla, Calocedrus formosana, Platycladus orientalis and Taiwanofungus camphoratus. It was first documented in 2006 (PMID: 16643055). Based on a literature review very few articles have been published on pinusolidic acid (PMID: 28691856).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    1.5547    2.4915    1.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4817    1.7166    1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    2.3084    1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0472    1.5915    1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262    0.1867    0.7423 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0336   -0.4903    0.2847 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8939   -0.7273    1.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9186    0.1466   -0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7564    1.1990   -1.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495   -0.5051   -0.9049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.8920   -0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589   -2.2296    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124   -1.2063   -0.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5863    0.1140   -0.1248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7019    1.1960   -1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5652    0.3465    0.8077 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8807   -0.1399    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5360    0.3301   -0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8564   -0.3659   -0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091    0.2637   -0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494   -0.6902   -0.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5334   -1.9415   -1.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1526   -1.7914   -0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2782   -2.7248   -0.9552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5046    3.4941    1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220    2.0749    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8417    3.3395    1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7806    2.5485    2.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6929    2.2014    0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6764    1.4731    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5169   -0.3795    1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668   -1.5753    1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2251   -1.0212    2.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4798    0.1652    1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2516   -1.5057   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020   -2.6609    0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8688   -1.9155   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602   -2.2353    1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816   -3.2132   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0821   -1.1370   -1.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.5593   -1.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2519    2.0921   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2800    1.5841   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1680    0.7497   -2.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3149   -0.2924    1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441   -1.2557    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5904    0.0614    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312    0.0336   -1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    1.4029   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978    1.3480   -0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8221   -0.5447   -0.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7610   -0.4592   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  6
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
  6  8  1  6
  8 10  1  0
  8  9  2  0
  5 14  1  0
 23 19  1  0
 16 14  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 13 40  1  0
 13 41  1  0
 12 38  1  0
 12 39  1  0
 11 36  1  0
 11 37  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  5 31  1  1
  4 29  1  0
  4 30  1  0
  3 27  1  0
  3 28  1  0
  1 25  1  0
  1 26  1  0
 16 45  1  1
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 10 35  1  0
M  END


  Mrv1652306302200142D          

 24 26  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6914   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2118    0.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
  6 21  1  1  0  0  0
  6 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC[C@@](C)([C@@H]1CCC(=C)[C@@H]2CCC1=CCOC1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-13-5-8-16-19(2,10-4-11-20(16,3)18(22)23)15(13)7-6-14-9-12-24-17(14)21/h9,15-16H,1,4-8,10-12H2,2-3H3,(H,22,23)/t15-,16+,19+,20-/m0/s1

> <INCHI_KEY>
FHQSDRHZGCMBKG-FIYPYCPBSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

$$$$

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.247  -7.835   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.771  -9.300   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.231  -9.300   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.291  -7.359   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.093   2.666   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.262   1.413   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21   22                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19                                                            
CONECT   21    6                                                            
CONECT   22    6   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Pinusolidate	Generator

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12CCC[C@@](C)([C@@H]1CCC(=C)[C@@H]2CCC1=CCOC1=O)C(O)=O

InChI Identifier

InChI=1S/C20H28O4/c1-13-5-8-16-19(2,10-4-11-20(16,3)18(22)23)15(13)7-6-14-9-12-24-17(14)21/h9,15-16H,1,4-8,10-12H2,2-3H3,(H,22,23)/t15-,16+,19+,20-/m0/s1

InChI Key

FHQSDRHZGCMBKG-FIYPYCPBSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Agathis macrophylla	LOTUS Database	35616633
Calocedrus formosana	LOTUS Database	35616633
Platycladus orientalis	LOTUS Database	35616633
Taiwanofungus camphoratus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Clerodane diterpenoid
Diterpenoid
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00022770

Chemspider ID

23339449

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25880646

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen CC, Shiao YJ, Lin RD, Shao YY, Lai MN, Lin CC, Ng LT, Kuo YH: Neuroprotective diterpenes from the fruiting body of Antrodia camphorata. J Nat Prod. 2006 Apr;69(4):689-91. doi: 10.1021/np0581263. [PubMed:16643055 ]
Sa NH, Tam NT, Anh NTH, Quan TD, Thien DD, Phong DT, Sung TV, Thuy TT: Chemical constituents from the leaves of Pinus dalatensis Ferre. Nat Prod Res. 2018 Feb;32(3):341-345. doi: 10.1080/14786419.2017.1350672. Epub 2017 Jul 10. [PubMed:28691856 ]

Showing NP-Card for Pinusolidic acid (NP0141171)

MOL for NP0141171 (Pinusolidic acid)

3D MOL for NP0141171 (Pinusolidic acid)

3D SDF for NP0141171 (Pinusolidic acid)

3D-SDF for NP0141171 (Pinusolidic acid)

PDB for NP0141171 (Pinusolidic acid)

3D PDB for NP0141171 (Pinusolidic acid)

SMILES for NP0141171 (Pinusolidic acid)

INCHI for NP0141171 (Pinusolidic acid)

Structure for NP0141171 (Pinusolidic acid)

3D Structure for NP0141171 (Pinusolidic acid)