NP-MRD: Showing NP-Card for Cynaropicrin (NP0044133)

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Record Information

Version

1.0

Created at

2021-11-12 23:51:58 UTC

Updated at

2021-11-26 17:45:47 UTC

NP-MRD ID

NP0044133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cynaropicrin

Description

Cynaropicrin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Cynaropicrin is found in Centaurea repens, Amberboa muricata, Anacyclus monanthos, Artemisia xerophytica, Brachylaena huillensis, Centaurea behen, Centaurea deflexa, Centaurea hermannii, Centaurea kotschyi, Centaurea macrocephala, Centaurea melitensis, Centaurea ptosimopappoides, Leuzea rhaponticoides, Centaurea scoparia, Centaurea solstitialis, Centaurothamnus maximus, Cheirolophus canariensis, Cheirolophus mauritanicus, Cheirolophus teydis, Cousinia adenosticta, Cousinia piptocephala, Cynara humilis, Grossheimia macrocephala, Himalaiella deltoidea, Himalaiella heteromalla, Oligochaeta divaricata, Pleiotaxis rugosa, Psephellus bellus, Psephellus phaeopappoides, Pseudostifftia kingii, Rhaponticum exaltatum, Rhaponticum serratuloides, Saussurea amara, Saussurea amurensis, Saussurea costus, Saussurea eopygmaea, Saussurea neopulchella, Saussurea puchella, Saussurea pulchella , Saussurea salicifolia, Volutaria crupinoides and Volutaria tubuliflora. It was first documented in 2019 (PMID: 30634079). Cynaropicrin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
    4.1146    1.9975   -0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545    0.8632    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7551    0.5052    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8320    0.3681    1.7481 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -0.0431    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847   -1.1195    0.9776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851    0.2712    0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410   -0.4666    0.3657 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1021    0.3191    1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518    1.3870    0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    2.5381    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    1.3526    0.3691 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9378    0.8950    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2210    0.5297    0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9855   -0.3109    1.6330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400   -0.1527   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -0.9537   -1.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    0.2259   -0.6062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4746   -0.9895   -0.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9994   -2.0345   -1.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650   -2.9117   -1.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776   -4.0875   -1.8422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913   -2.2054   -1.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747   -2.7500   -1.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265   -0.8255   -0.7630 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8955    2.6802   -0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    2.2572   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4317    1.3407    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0459   -0.4375   -0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9482    0.3904    2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1631   -1.4091    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674   -0.3271    2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722    0.8265    2.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    2.7004    0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353    3.3590    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4511    2.2938   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302   -0.0253    1.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895    1.7101    2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537    1.4674    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7221    0.2165    1.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551   -1.4304   -2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4924   -1.1311   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857    0.5366   -1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5631   -1.3222    0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5535   -3.7664   -1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118   -2.2327   -1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0690   -0.0991   -1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  2  3
 10  9  1  0
  9  8  1  0
  8 25  1  0
 25 19  1  0
 19 18  1  0
 18 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 16 17  2  3
 14 15  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  3
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 12 10  1  0
 23 25  1  0
 16 18  1  0
 11 34  1  0
 11 35  1  0
  9 32  1  0
  9 33  1  0
  8 31  1  1
 25 47  1  6
 19 44  1  1
 18 43  1  6
 12 36  1  6
 13 37  1  0
 13 38  1  0
 14 39  1  6
 17 41  1  0
 17 42  1  0
 15 40  1  0
 24 45  1  0
 24 46  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
M  END


  Mrv1652311132100522D          

 25 27  0  0  1  0            999 V2000
   -0.4082    3.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    3.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    2.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    1.9557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8827    2.3137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0663    3.1180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5519    3.7630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7269    3.7630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4720    4.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    5.0325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8069    4.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915    4.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    5.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    3.1919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0165    2.2497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5909    1.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    1.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -0.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105    1.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105    1.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -0.1068    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
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  1  0  0  0
 11 12  2  0  0  0  0
 10 13  1  1  0  0  0
  6 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  5 17  1  1  0  0  0
 17 18  2  0  0  0  0
  4 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
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(=C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1

> <INCHI_KEY>
KHSCYOFDKADJDJ-NQLMQOPMSA-N

> <FORMULA>
C19H22O6

> <MOLECULAR_WEIGHT>
346.379

> <EXACT_MASS>
346.141638428

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.92729774559407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
1.0448134336666668

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.074033815453497

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.422366385522363

> <JCHEM_PKA_STRONGEST_BASIC>
-2.844123071929464

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
88.98859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cynaropicrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0      -0.762   6.163   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.263   5.820   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.606   4.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.994   3.651   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.381   4.319   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.724   5.820   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.764   7.024   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.224   7.024   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.748   8.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.994   9.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.239   8.489   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.704   8.965   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.994  10.934   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -7.258   5.958   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -7.863   4.542   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -9.364   4.200   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.703   3.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.841   1.995   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.994   2.111   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.660   1.341   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.660  -0.199   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.326   2.111   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.326   3.651   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.007   1.341   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.007  -0.199   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    6   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18                                                  
CONECT   18   17                                                            
CONECT   19    4   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₆

Average Mass

346.3790 Da

Monoisotopic Mass

346.14164 Da

IUPAC Name

(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

Traditional Name

cynaropicrin

CAS Registry Number

Not Available

SMILES

OCC(=C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1

InChI Key

KHSCYOFDKADJDJ-NQLMQOPMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acroptilon repens	Plant	KNApSAcK
Amberboa muricata	Plant	KNApSAcK
Anacyclus monanthos	LOTUS Database	35616633
Artemisia xerophytica	LOTUS Database	35616633
Brachylaena huillensis	LOTUS Database	35616633
Centaurea behen	LOTUS Database	35616633
Centaurea deflexa	LOTUS Database	35616633
Centaurea hermannii	LOTUS Database	35616633
Centaurea kotschyi	LOTUS Database	35616633
Centaurea macrocephala	LOTUS Database	35616633
Centaurea melitensis	LOTUS Database	35616633
Centaurea ptosimopappoides	LOTUS Database	35616633
Centaurea rhaponticoides	LOTUS Database	35616633
Centaurea scoparia	LOTUS Database	35616633
Centaurea solstitialis	LOTUS Database	35616633
Centaurothamnus maximus	LOTUS Database	35616633
Cheirolophus canariensis	LOTUS Database	35616633
Cheirolophus mauritanicus	LOTUS Database	35616633
Cheirolophus teydis	LOTUS Database	35616633
Cousinia adenosticta	LOTUS Database	35616633
Cousinia piptocephala	LOTUS Database	35616633
Cynara cardunculus	FooDB	KNAPSACK
Cynara humilis	LOTUS Database	35616633
Cynara scolymus	FooDB	KNAPSACK
Grossheimia macrocephala	Plant	KNApSAcK
Jurinea deltoidea	LOTUS Database	35616633
Jurinea heteromalla	LOTUS Database	35616633
Oligochaeta divaricata	LOTUS Database	35616633
Pleiotaxis rugosa	LOTUS Database	35616633
Psephellus bellus	LOTUS Database	35616633
Psephellus phaeopappoides	LOTUS Database	35616633
Pseudostifftia kingii	LOTUS Database	35616633
Rhaponticum exaltatum	LOTUS Database	35616633
Rhaponticum serratuloides	LOTUS Database	35616633
Saussurea amara	Plant	KNApSAcK
Saussurea amurensis	LOTUS Database	35616633
Saussurea costus	LOTUS Database	35616633
Saussurea eopygmaea	LOTUS Database	35616633
Saussurea neopulchella	Plant	KNApSAcK
Saussurea puchella	Plant	KNApSAcK
Saussurea pulchella	Plant	KNApSAcK
Saussurea salicifolia	LOTUS Database	35616633
Volutaria crupinoides	LOTUS Database	35616633
Volutaria tubuliflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:4038 )
Guaianolide (C09385 )

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	0.54	ALOGPS
logP	1.04	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.99 m³·mol⁻¹	ChemAxon
Polarizability	34.93 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

C00003243

Chemspider ID

Not Available

KEGG Compound ID

C09385

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cynaropicrin

METLIN ID

Not Available

PubChem Compound

119093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nawrot J, Budzianowski J, Nowak G: Phytochemical profiles of the leaves of Stizolophus balsamita and Psephellus sibiricus and their chemotaxonomic implications. Phytochemistry. 2019 Mar;159:172-178. doi: 10.1016/j.phytochem.2018.12.022. Epub 2019 Jan 9. [PubMed:30634079 ]

Showing NP-Card for Cynaropicrin (NP0044133)

MOL for NP0044133 (Cynaropicrin)

3D MOL for NP0044133 (Cynaropicrin)

3D SDF for NP0044133 (Cynaropicrin)

3D-SDF for NP0044133 (Cynaropicrin)

PDB for NP0044133 (Cynaropicrin)

3D PDB for NP0044133 (Cynaropicrin)

SMILES for NP0044133 (Cynaropicrin)

INCHI for NP0044133 (Cynaropicrin)

Structure for NP0044133 (Cynaropicrin)

3D Structure for NP0044133 (Cynaropicrin)