NP-MRD: Showing NP-Card for (1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid (NP0286118)

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Record Information

Version

2.0

Created at

2022-09-09 14:33:40 UTC

Updated at

2022-09-09 14:33:40 UTC

NP-MRD ID

NP0286118

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid

Description

Grindelic acid, also known as grindelate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid is found in Grindelia hirsutula, Grindelia squarrosa, Isocoma tenuisecta and Xanthocephalum gymnospermoides. (1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid was first documented in 2005 (PMID: 16010831). Based on a literature review a small amount of articles have been published on Grindelic acid (PMID: 33536899) (PMID: 31644941) (PMID: 26119826) (PMID: 23831507).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    1.5529   -0.7643   -3.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -0.2189   -1.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746    0.8285   -2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9548    1.4593   -1.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2076    0.6039   -0.0079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5424    0.8143    0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466    1.9186    1.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6081    1.3201   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1096   -0.3848    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8926   -1.0162    1.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1523   -1.7446    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8316   -0.8391   -0.2827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4897   -1.4054   -1.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6700   -0.7609   -0.5889 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3980   -2.0304   -0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -1.7306    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5229   -0.2403    0.5998 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6283    0.0527   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8463    0.4287    1.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9853    1.8842    1.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1431    2.4450    1.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384    2.7260    1.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820    0.2194    0.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953   -0.3402   -3.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316   -1.8630   -3.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -0.3851   -4.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0705    1.2550   -3.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730    2.4215   -0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8925    1.8128   -1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553    0.9163    0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3933    2.4778    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571    2.6163    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2370    1.4992    2.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7537    0.7099   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4861    2.4055   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5793    1.2759    0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952   -0.0397    2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011   -1.1198    0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -1.7786    2.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249   -0.2851    2.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3162   -2.2310    1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8804   -2.5645    0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218   -1.8794   -2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870   -2.2592   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078   -0.6585   -2.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654   -2.3157   -1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -2.9172   -0.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260   -2.0029    1.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3621   -2.2655    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -0.8124   -1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5977    0.1673    0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542    0.9347   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8223    0.0606    2.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0424    0.2858    2.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972    3.3141    0.4670 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
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 17 23  1  0
 14  2  1  0
 14 23  1  1
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
M  END


  Mrv1652309092216332D          

 23 25  0  0  1  0            999 V2000
    2.2871    1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789    1.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4683    1.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553    0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    0.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2685    0.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5437    1.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6317   -0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0294   -0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2400   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530    0.1782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6543   -0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    0.4179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3656   -0.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -0.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.1484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3781    0.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644   -1.2397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    0.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4534    0.5739    0.0000 O   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 14 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0286118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2C(C)(C)CCC[C@]2(C)[C@@]11CC[C@](C)(CC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-14-7-8-15-17(2,3)9-6-10-19(15,5)20(14)12-11-18(4,23-20)13-16(21)22/h7,15H,6,8-13H2,1-5H3,(H,21,22)/t15?,18-,19+,20-/m1/s1

> <INCHI_KEY>
XLWWERNKTLITEF-FOUFQHLJSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
36.85610312592476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,5'R,8aS)-2,5,5,5',8a-pentamethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl]acetic acid

> <JCHEM_LOGP>
4.388543421333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.863533010608794

> <JCHEM_PKA_STRONGEST_BASIC>
-4.244857782038335

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
91.63609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5'R,8aS)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-ylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.269   2.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.743   2.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.867   3.332   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.341   2.885   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.690   1.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.163   0.937   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.701   1.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.348   2.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.513  -0.563   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.388  -1.615   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.915  -1.167   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.566   0.333   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.821  -1.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.092   0.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.282  -0.748   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.888  -1.401   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.836  -0.277   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.572   0.604   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.827  -1.441   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.315  -1.150   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.307  -2.314   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.811   0.305   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.580   1.071   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12    2   15   23                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Grindelate	Generator

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4730 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

2-[(1R,5'R,8aS)-2,5,5,5',8a-pentamethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl]acetic acid

Traditional Name

(1R,5'R,8aS)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-ylacetic acid

CAS Registry Number

Not Available

SMILES

CC1=CCC2C(C)(C)CCC[C@]2(C)[C@@]11CC[C@](C)(CC(O)=O)O1

InChI Identifier

InChI=1S/C20H32O3/c1-14-7-8-15-17(2,3)9-6-10-19(15,5)20(14)12-11-18(4,23-20)13-16(21)22/h7,15H,6,8-13H2,1-5H3,(H,21,22)/t15?,18-,19+,20-/m1/s1

InChI Key

XLWWERNKTLITEF-FOUFQHLJSA-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
Grindelia hirsutula	LOTUS Database	35616633
Grindelia squarrosa	LOTUS Database	35616633
Isocoma tenuisecta	LOTUS Database	35616633
Xanthocephalum gymnospermoides	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

Diterpenoid
Grindelane diterpenoid
Tetrahydrofuran
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	4.39	ChemAxon
pKa (Strongest Acidic)	4.86	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.64 m³·mol⁻¹	ChemAxon
Polarizability	36.86 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003462

Chemspider ID

16735839

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20054931

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gierlikowska B, Filipek A, Gierlikowski W, Kania D, Stefanska J, Demkow U, Kiss AK: Grindelia squarrosa Extract and Grindelic Acid Modulate Pro-inflammatory Functions of Respiratory Epithelium and Human Macrophages. Front Pharmacol. 2021 Jan 18;11:534111. doi: 10.3389/fphar.2020.534111. eCollection 2020. [PubMed:33536899 ]
Gierlikowska B, Gierlikowski W, Bekier K, Skalicka-Wozniak K, Czerwinska ME, Kiss AK: Inula helenium and Grindelia squarrosa as a source of compounds with anti-inflammatory activity in human neutrophils and cultured human respiratory epithelium. J Ethnopharmacol. 2020 Mar 1;249:112311. doi: 10.1016/j.jep.2019.112311. Epub 2019 Oct 20. [PubMed:31644941 ]
Zerbe P, Rodriguez SM, Mafu S, Chiang A, Sandhu HK, O'Neil-Johnson M, Starks CM, Bohlmann J: Exploring diterpene metabolism in non-model species: transcriptome-enabled discovery and functional characterization of labda-7,13E-dienyl diphosphate synthase from Grindelia robusta. Plant J. 2015 Sep;83(5):783-93. doi: 10.1111/tpj.12925. Epub 2015 Jul 23. [PubMed:26119826 ]
Reta GF, Chiaramello AI, Garcia C, Leon LG, Martin VS, Padron JM, Tonn CE, Donadel OJ: Derivatives of grindelic acid: from a non-active natural diterpene to synthetic antitumor derivatives. Eur J Med Chem. 2013 Sep;67:28-38. doi: 10.1016/j.ejmech.2013.06.013. Epub 2013 Jun 18. [PubMed:23831507 ]
Orden AA, Cifuente DA, Borkowski EJ, Tonn CE, Sanz MK: Stereo- and regioselective hydroxylation of grindelic acid derivatives by Aspergillus niger. Nat Prod Res. 2005 Sep;19(6):625-31. doi: 10.1080/14786410512331330693. [PubMed:16010831 ]
LOTUS database [Link]

Showing NP-Card for (1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid (NP0286118)

MOL for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D MOL for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D SDF for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D-SDF for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

PDB for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D PDB for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

SMILES for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

INCHI for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

Structure for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D Structure for NP0286118 ((1r,5'r,8as)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)