NP-MRD: Showing NP-Card for Cnicin (NP0140430)

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Record Information

Version

2.0

Created at

2022-06-29 21:33:54 UTC

Updated at

2022-06-29 21:33:54 UTC

NP-MRD ID

NP0140430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cnicin

Description

Cnicin belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Cnicin is found in Centaurea aegialophila, Centaurea affinis, Centaurea alba, Centaurea alexandrina, Centaurea arenaria, Centaurea aspera, Centaurea benedicta, Centaurea brugueriana, Centaurea calcitrapa, Centaurea cineraria, Centaurea cuneifolia, Centaurea deusta, Centaurea diffusa, Centaurea granatensis, Centaurea napifolia, Centaurea pallescens, Centaurea paniculata, Centaurea paui, Centaurea spinosa, Centaurea stoebe and Centaurea sulphurea. Cnicin was first documented in 2020 (PMID: 33628288). Based on a literature review a small amount of articles have been published on Cnicin (PMID: 35533533) (PMID: 35011381) (PMID: 34066998) (PMID: 33164156).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223332D          

 27 28  0  0  1  0            999 V2000
    1.8079   -1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  2  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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719    0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239    1.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    0.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    1.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -0.2730    0.0000 O   0  0  0  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   -2.0625    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  2  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
  2 11  1  0  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  6  0  0  0
  9 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  8 25  1  1  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
    3.0974    1.5086    1.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918    0.8205    0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    0.1845   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8484   -0.4906   -1.2445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033    0.3093    0.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -0.2582   -0.7224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4101   -1.3514    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1783   -2.4038   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -3.0844   -1.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3782   -2.8070   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814   -2.2457    1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9786   -1.0784    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4876    0.2209    1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649    0.6683    2.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629    1.9044    2.8476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7151    0.9502    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716    0.6217   -0.8812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8105    1.6754   -1.7203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    2.1069   -2.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9464    3.0244   -3.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6710    1.2979   -2.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2786    1.0413   -3.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948    0.8544   -0.9813 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9282    0.6880    0.3408 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1479    1.2441   -0.9222 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8022    1.3983    1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1271    1.2196    0.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    1.9959    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568    1.6476    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5773   -0.7671   -1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5186   -1.8762    0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772   -0.9325    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720   -2.9496   -1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -2.6810   -2.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -4.1576   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046   -3.6115   -0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314   -1.8892    1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6813   -3.0797    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9590   -1.2644    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2348   -1.0640   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9779    0.7678    2.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4822   -0.0185    3.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346    2.5711    3.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    1.9162    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478   -0.2765   -1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927    1.4650   -4.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439    0.4528   -3.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    1.7885   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.3889    0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1304    0.5581   -1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    1.0217    2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5842    2.4880    1.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3552    0.2652    1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  3
 21 23  1  0
 23  6  1  0
  6  7  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  7  8  1  0
 23 17  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  6
 22 46  1  0
 22 47  1  0
 23 48  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  1 28  1  0
  1 29  1  0
 24 49  1  6
 25 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
M  END


  Mrv1652306292223332D          

 27 28  0  0  1  0            999 V2000
    1.8079   -1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  2  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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719    0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239    1.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    0.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    1.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -0.2730    0.0000 O   0  0  0  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   -2.0625    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  2  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
  2 11  1  0  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  6  0  0  0
  9 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  8 25  1  1  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C1)OC(=O)C(=C)[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16-,17+,18+/m0/s1

> <INCHI_KEY>
ZTDFZLVUIVPZDU-QGNHJMHWSA-N

> <FORMULA>
C20H26O7

> <MOLECULAR_WEIGHT>
378.421

> <EXACT_MASS>
378.167853177

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.303642138959745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (3R)-3,4-dihydroxy-2-methylidenebutanoate

> <ALOGPS_LOGP>
0.96

> <JCHEM_LOGP>
1.1054298313333335

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.01379948012794

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.52151690532435

> <JCHEM_PKA_STRONGEST_BASIC>
-2.734788470651095

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
99.18529999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cnicin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       3.375  -2.443   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   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       5.335  -1.540   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  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337  -1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.681   0.736   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.711   1.881   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.149   0.897   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.379   2.231   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.523  -0.510   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    2                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21    9   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    8                                                       
CONECT   26    6   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₇

Average Mass

378.4210 Da

Monoisotopic Mass

378.16785 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C1=C/CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C1)OC(=O)C(=C)[C@@H](O)CO

InChI Identifier

InChI=1S/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16-,17+,18+/m0/s1

InChI Key

ZTDFZLVUIVPZDU-QGNHJMHWSA-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
Centaurea aegialophila	LOTUS Database	35616633
Centaurea affinis	LOTUS Database	35616633
Centaurea alba	LOTUS Database	35616633
Centaurea alexandrina	LOTUS Database	35616633
Centaurea arenaria	LOTUS Database	35616633
Centaurea aspera	LOTUS Database	35616633
Centaurea benedicta	LOTUS Database	35616633
Centaurea brugueriana	LOTUS Database	35616633
Centaurea calcitrapa	LOTUS Database	35616633
Centaurea cineraria	LOTUS Database	35616633
Centaurea cuneifolia	LOTUS Database	35616633
Centaurea deusta	LOTUS Database	35616633
Centaurea diffusa	LOTUS Database	35616633
Centaurea granatensis	LOTUS Database	35616633
Centaurea napifolia	LOTUS Database	35616633
Centaurea pallescens	LOTUS Database	35616633
Centaurea paniculata	LOTUS Database	35616633
Centaurea paui	LOTUS Database	35616633
Centaurea spinosa	LOTUS Database	35616633
Centaurea stoebe	LOTUS Database	35616633
Centaurea sulphurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

germacranolide (CHEBI:3768 )
Germacrenes (C09362 )

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

C00003232

Chemspider ID

4444781

KEGG Compound ID

C09362

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cnicin

METLIN ID

Not Available

PubChem Compound

5281435

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1701461

References

General References

Avula B, Katragunta K, Wang YH, Ali Z, Khan IA: Simultaneous determination and characterization of flavonoids, sesquiterpene lactone, and other phenolics from Centaurea benedicta and dietary supplements using UHPLC-PDA-MS and LC-DAD-QToF. J Pharm Biomed Anal. 2022 Jul 15;216:114806. doi: 10.1016/j.jpba.2022.114806. Epub 2022 May 4. [PubMed:35533533 ]
Possart K, Herrmann FC, Jose J, Costi MP, Schmidt TJ: Sesquiterpene Lactones with Dual Inhibitory Activity against the Trypanosoma brucei Pteridine Reductase 1 and Dihydrofolate Reductase. Molecules. 2021 Dec 27;27(1):149. doi: 10.3390/molecules27010149. [PubMed:35011381 ]
Alhadrami HA, Sayed AM, Hassan HM, Youssif KA, Gaber Y, Moatasim Y, Kutkat O, Mostafa A, Ali MA, Rateb ME, Abdelmohsen UR, Gamaleldin NM: Cnicin as an Anti-SARS-CoV-2: An Integrated In Silico and In Vitro Approach for the Rapid Identification of Potential COVID-19 Therapeutics. Antibiotics (Basel). 2021 May 7;10(5):542. doi: 10.3390/antibiotics10050542. [PubMed:34066998 ]
Ahmadimoghaddam D, Sadeghian R, Ranjbar A, Izadidastenaei Z, Mohammadi S: Antinociceptive activity of Cnicus benedictus L. leaf extract: a mechanistic evaluation. Res Pharm Sci. 2020 Oct 19;15(5):463-472. doi: 10.4103/1735-5362.297849. eCollection 2020 Oct. [PubMed:33628288 ]
Queiroz LS, Ferreira EA, Mengarda AC, Almeida ADC, Pinto PF, Coimbra ES, de Moraes J, Denadai AML, Da Silva Filho AA: In vitro and in vivo evaluation of cnicin from blessed thistle (Centaurea benedicta) and its inclusion complexes with cyclodextrins against Schistosoma mansoni. Parasitol Res. 2021 Apr;120(4):1321-1333. doi: 10.1007/s00436-020-06963-2. Epub 2020 Nov 8. [PubMed:33164156 ]

Showing NP-Card for Cnicin (NP0140430)

MOL for NP0140430 (Cnicin)

3D MOL for NP0140430 (Cnicin)

3D SDF for NP0140430 (Cnicin)

3D-SDF for NP0140430 (Cnicin)

PDB for NP0140430 (Cnicin)

3D PDB for NP0140430 (Cnicin)

SMILES for NP0140430 (Cnicin)

INCHI for NP0140430 (Cnicin)

Structure for NP0140430 (Cnicin)

3D Structure for NP0140430 (Cnicin)