NP-MRD: Showing NP-Card for Pimaric acid (NP0137584)

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Record Information

Version

2.0

Created at

2022-05-30 16:56:55 UTC

Updated at

2022-05-30 16:56:55 UTC

NP-MRD ID

NP0137584

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pimaric acid

Description

PIMARIC ACID, also known as dextropimarate or usic acid, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Pimaric acid is found in Agathis australis, Aldama arenaria, Apis mellifera, Aralia cordata, Calamus draco, Cedrus atlantica, Chamaecyparis formosensis, Chamaecyparis pisifera, Anisochilus harmandii, Cryptomeria japonica, Cupressus sempervirens, Eleutherococcus trifoliatus, Ferula marmarica, Herbertus sakuraii, Juniperus brevifolia, Juniperus chinensis, Juniperus communis, Juniperus formosana, Juniperus phoenicea, Juniperus rigida, Juniperus sabina, Juniperus thurifera, Larix gmelinii, Mastigophora diclados, Mitrephora celebica, Picea jezoensis, Pinus massoniana, Pinus merkusii, Pinus nigra, Pinus palustris, Pinus pinaster, Pinus pumila, Pinus resinosa, Pinus taeda, Pinus yunnanensis, Platycladus orientalis, Pseudognaphalium gaudichaudianum, Sagittaria pygmaea, Taxus mairei, Thuja standishii and Viguiera arenaria. Pimaric acid was first documented in 2018 (PMID: 30092384). PIMARIC ACID is a weakly acidic compound (based on its pKa) (PMID: 32316044) (PMID: 31591296) (PMID: 31539010) (PMID: 30572688).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    4.6027    1.1215   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    0.0795    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3621   -0.4541    0.7209 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6410   -1.0616    2.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528    0.6803    0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738    0.7215    0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3530    1.9073    0.8431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    1.7069    0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5146    0.3216    0.4638 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9860    0.1657    0.2012 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7960    1.2851    0.8318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4813   -1.0903    0.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -1.9767    0.1307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3541   -1.2656    2.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3229    0.1011   -1.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6059   -0.9923   -1.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2911   -1.3521   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -0.1510   -0.7050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4306    0.9323   -1.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6654   -0.5145   -0.0998 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6778   -1.0939   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475   -1.5431   -0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5022    1.5228   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6313    1.5868   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5760   -0.3702    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080   -1.5861    2.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4974   -1.7608    2.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8044   -0.2151    2.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493    1.5551    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5668    2.7458    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7237    2.3345    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4779    1.8724    1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6665    2.4941    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -0.3311    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    0.9850    0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7025    2.2372    0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777    1.3638    1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055   -2.0753    2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4233   -0.1537   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    1.0870   -1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4570   -0.6575   -3.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987   -1.9272   -2.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -2.1522   -0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344   -1.7327   -2.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723    1.8523   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    1.1987   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7247    0.5500   -2.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4761   -1.2481    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685   -2.0035   -1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -0.3811   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4294   -2.3788    0.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6768   -1.9395   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
  3  4  1  0
  3  2  1  6
  2  1  2  3
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 10 12  1  1
 12 14  1  0
 12 13  2  0
  6 20  1  0
 18  9  1  0
 18 20  1  0
 20 48  1  1
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  2 25  1  0
  1 23  1  0
  1 24  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 11 35  1  0
 11 36  1  0
 11 37  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 14 38  1  0
M  END


  Mrv1652309272006282D          

 24 26  0  0  0  0            999 V2000
10012.098510013.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.957910014.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.673610014.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.244310015.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.815010012.5983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10011.384810013.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.670310013.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.099410013.0112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.813610013.4238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.813610011.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.528110012.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.528110013.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.528710014.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.814210014.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.243110013.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.243110014.2487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.098910011.4727    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10010.670110012.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.099810012.1862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.868110011.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.911610011.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.384710011.7735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10010.051610011.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.168010010.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 15 16  1  0  0  0  0
 16  2  1  0  0  0  0
 16  4  1  6  0  0  0
 14  9  1  0  0  0  0
  9  5  1  6  0  0  0
 12 15  2  0  0  0  0
  9  8  1  0  0  0  0
  8  1  1  1  0  0  0
 19 17  1  6  0  0  0
 22 20  1  6  0  0  0
 22 21  1  0  0  0  0
 20 23  1  0  0  0  0
 18 22  1  0  0  0  0
 22 19  1  0  0  0  0
 20 24  2  0  0  0  0
  7 18  1  0  0  0  0
 19  8  1  0  0  0  0
 19 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@@](C)(C=C)C=C1CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1

> <INCHI_KEY>
MHVJRKBZMUDEEV-APQLOABGSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.523694020535586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
5.067184579000001

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.804649127247729

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.33479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.65e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pimaric acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8689.2508692.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8694.5888694.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8695.9248693.264   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8693.2568694.804   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8690.5888690.183   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8687.9188691.724   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8686.5858690.954   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8689.2528690.954   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8690.5858691.724   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8690.5858688.645   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8691.9198689.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8691.9198690.954   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8691.9208694.034   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8690.5868693.264   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8693.2548691.724   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8693.2548693.264   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0    8689.2518688.082   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0    8686.5848689.414   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8689.2538689.414   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8686.9548687.441   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8688.9028687.459   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8687.9188688.644   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8685.4308687.674   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8687.5148686.004   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3   16                                                       
CONECT    3    2                                                            
CONECT    4   16                                                            
CONECT    5    9                                                            
CONECT    6    7    8                                                       
CONECT    7    6   18                                                       
CONECT    8    6    9    1   19                                             
CONECT    9   12   14    5    8                                             
CONECT   10   11   19                                                       
CONECT   11   10   12                                                       
CONECT   12    9   11   15                                                  
CONECT   13   14   16                                                       
CONECT   14   13    9                                                       
CONECT   15   16   12                                                       
CONECT   16   13   15    2    4                                             
CONECT   17   19                                                            
CONECT   18   22    7                                                       
CONECT   19   17   22    8   10                                             
CONECT   20   22   23   24                                                  
CONECT   21   22                                                            
CONECT   22   20   21   18   19                                             
CONECT   23   20                                                            
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Dextropimaric acid	Kegg
Dextropimarate	Generator
PIMARate	Generator
Pimara-8(14),15-dien-19-Oic acid	MeSH
Usic acid	MeSH
Pimaradienoic acid	MeSH
Pimaric acid, (L)-isomer	MeSH
13alpha-Methyl-13-vinylpodocarp-8(14)-en-15-oic acid	PhytoBank
13α-Methyl-13-vinylpodocarp-8(14)-en-15-oic acid	PhytoBank
8(14),15-Pimaradien-18-oic acid	PhytoBank
Pimaric acid	PhytoBank
d-Pimaric acid	PhytoBank
alpha-Pimaric acid	PhytoBank
α-Pimaric acid	PhytoBank

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

Traditional Name

pimaric acid

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@@](C)(C=C)C=C1CC[C@@]1([H])[C@@](C)(CCC[C@]21C)C(O)=O

InChI Identifier

InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1

InChI Key

MHVJRKBZMUDEEV-APQLOABGSA-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 australis	LOTUS Database	35616633
Aldama arenaria	LOTUS Database	35616633
Apis mellifera	LOTUS Database	35616633
Aralia cordata	LOTUS Database	35616633
Calamus draco	LOTUS Database	35616633
Cedrus atlantica	LOTUS Database	35616633
Chamaecyparis formosensis	LOTUS Database	35616633
Chamaecyparis pisifera	LOTUS Database	35616633
Coleus harmandii	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cupressus sempervirens	LOTUS Database	35616633
Eleutherococcus trifoliatus	LOTUS Database	35616633
Ferula marmarica	LOTUS Database	35616633
Herbertus sakuraii	LOTUS Database	35616633
Juniperus brevifolia	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Juniperus formosana	LOTUS Database	35616633
Juniperus phoenicea	LOTUS Database	35616633
Juniperus rigida	LOTUS Database	35616633
Juniperus sabina	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Mastigophora diclados	LOTUS Database	35616633
Mitrephora celebica	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Pinus massoniana	LOTUS Database	35616633
Pinus merkusii	LOTUS Database	35616633
Pinus nigra	LOTUS Database	35616633
Pinus palustris	LOTUS Database	35616633
Pinus pinaster	LOTUS Database	35616633
Pinus pumila	LOTUS Database	35616633
Pinus resinosa	LOTUS Database	35616633
Pinus taeda	LOTUS Database	35616633
Pinus yunnanensis	LOTUS Database	35616633
Platycladus orientalis	LOTUS Database	35616633
Pseudognaphalium gaudichaudianum	LOTUS Database	35616633
Sagittaria pygmaea	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Thuja standishii	LOTUS Database	35616633
Viguiera arenaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Pimarane diterpenoid
Diterpenoid
Phenanthrene
Hydrophenanthrene
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpenoid (CHEBI:39 )
Pimaranes (C09159 )

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	4.95	ALOGPS
logP	5.07	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.33 m³·mol⁻¹	ChemAxon
Polarizability	35.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003468

Chemspider ID

191072

KEGG Compound ID

C09159

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

220338

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee S, Choi E, Yang SM, Ryoo R, Moon E, Kim SH, Kim KH: Bioactive compounds from sclerotia extract of Poria cocos that control adipocyte and osteoblast differentiation. Bioorg Chem. 2018 Dec;81:27-34. doi: 10.1016/j.bioorg.2018.07.031. Epub 2018 Jul 31. [PubMed:30092384 ]
Goels T, Eichenauer E, Langeder J, Hoeller F, Sykora C, Tahir A, Urban E, Heiss EH, Saukel J, Glasl S: Norway Spruce Balm: Phytochemical Composition and Ability to Enhance Re-epithelialization In Vitro. Planta Med. 2020 Oct;86(15):1080-1088. doi: 10.1055/a-1141-0921. Epub 2020 Apr 21. [PubMed:32316044 ]
Ioannidis K, Melliou E, Magiatis P: High-Throughput (1)H-Nuclear Magnetic Resonance-Based Screening for the Identification and Quantification of Heartwood Diterpenic Acids in Four Black Pine (Pinus nigra Arn.) Marginal Provenances in Greece. Molecules. 2019 Oct 7;24(19). pii: molecules24193603. doi: 10.3390/molecules24193603. [PubMed:31591296 ]
Atchan Nwakiban AP, Sokeng AJ, Dell'Agli M, Bossi L, Beretta G, Gelmini F, Deutou Tchamgoue A, Agbor Agbor G, Kuiate JR, Daglia M, Magni P: Hydroethanolic plant extracts from Cameroon positively modulate enzymes relevant to carbohydrate/lipid digestion and cardio-metabolic diseases. Food Funct. 2019 Oct 16;10(10):6533-6542. doi: 10.1039/c9fo01664c. [PubMed:31539010 ]
Simoneit BRT, Cox RE, Oros DR, Otto A: Terpenoid Compositions of Resins from Callitris Species (Cupressaceae). Molecules. 2018 Dec 19;23(12). pii: molecules23123384. doi: 10.3390/molecules23123384. [PubMed:30572688 ]

Showing NP-Card for Pimaric acid (NP0137584)

MOL for NP0137584 (Pimaric acid)

3D MOL for NP0137584 (Pimaric acid)

3D SDF for NP0137584 (Pimaric acid)

3D-SDF for NP0137584 (Pimaric acid)

PDB for NP0137584 (Pimaric acid)

3D PDB for NP0137584 (Pimaric acid)

SMILES for NP0137584 (Pimaric acid)

INCHI for NP0137584 (Pimaric acid)

Structure for NP0137584 (Pimaric acid)

3D Structure for NP0137584 (Pimaric acid)