NP-MRD: Showing NP-Card for (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate (NP0308752)

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Record Information

Version

2.0

Created at

2022-09-11 02:46:35 UTC

Updated at

2022-09-11 02:46:35 UTC

NP-MRD ID

NP0308752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate

Description

Episolstitiolide 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. (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate is found in Centaurea glastifolia and Centaurea solstitialis. Based on a literature review very few articles have been published on Episolstitiolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112204462D          

 27 30  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638    3.1199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7823    2.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    3.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2598   -1.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.2055    0.0000 Cl  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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  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
 18 17  1  6  0  0  0
 12 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -1.1541   -2.5928    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282   -1.3970    1.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -1.2786    0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1563   -0.2005   -0.0152 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4399    0.2813    0.3343 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489    0.1908   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3995   -0.3567   -1.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8971    0.6976   -0.1107 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1031    1.3516    1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282   -0.1372   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    1.1934   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1221    0.8999   -0.0974 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5626    1.9580   -1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543    2.7928   -0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    1.8849   -2.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0952    2.5180   -3.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    1.0419   -1.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205    0.2937   -0.7281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2217    0.4145    0.2961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7481   -0.4213    1.4752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9891   -0.9421    2.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1370   -0.7798    1.1059 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7777   -1.9621    0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -0.1075   -0.1027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3406    1.0240   -0.4228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5992   -0.9774   -1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340   -1.3489   -1.6216 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2075   -2.8224    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4868   -3.4038    0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1441   -1.0585    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513   -2.2612    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -0.6473   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9475    0.5604    2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1756    1.6247    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774    2.2375    1.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0148   -0.1118   -0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213   -0.9395   -1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    1.2905    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465    3.5680   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    2.7525    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0020   -0.7661   -0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2355    1.4676    0.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573    0.2579    2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9700   -2.0104    2.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2244   -0.3837    3.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8641   -0.0617    1.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6116   -2.6263    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4563    1.6064    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -1.9369   -1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2101   -0.3761   -2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
  8  6  1  6
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 24 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 13  1  0
 13 14  2  3
 13 12  1  0
 11  8  1  0
 12  4  1  0
 19 20  1  0
 12 18  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
  4 32  1  6
  3 30  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
 20 43  1  1
 21 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 19 42  1  1
 18 41  1  6
 14 39  1  0
 14 40  1  0
 12 38  1  1
M  END


  Mrv1652309112204462D          

 27 30  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638    3.1199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7823    2.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    3.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2598   -1.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.2055    0.0000 Cl  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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  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
 18 17  1  6  0  0  0
 12 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CO1)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)[C@](O)(CCl)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClO7/c1-8-4-11(26-17(23)18(3)7-25-18)13-9(2)16(22)27-15(13)14-10(8)5-12(21)19(14,24)6-20/h10-15,21,24H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18+,19+/m0/s1

> <INCHI_KEY>
VPRUEYOIZZTFET-ONCJGSTBSA-N

> <FORMULA>
C19H23ClO7

> <MOLECULAR_WEIGHT>
398.84

> <EXACT_MASS>
398.1132308

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.7864996154661

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2R)-2-methyloxirane-2-carboxylate

> <JCHEM_LOGP>
0.699114381

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.750061204456351

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.797944328654278

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2665841195282956

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
93.47559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2R)-2-methyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.665   3.341   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.435   4.864   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.001   5.426   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.639   5.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.794   4.805   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.903   7.176   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.442   7.138   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.218  -3.132   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.634  -2.601   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0       5.366  -4.117   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    8                                                       
CONECT   12    4   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   19   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃ClO₇

Average Mass

398.8400 Da

Monoisotopic Mass

398.11323 Da

IUPAC Name

(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2R)-2-methyloxirane-2-carboxylate

Traditional Name

(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2R)-2-methyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@]1(CO1)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)[C@](O)(CCl)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H23ClO7/c1-8-4-11(26-17(23)18(3)7-25-18)13-9(2)16(22)27-15(13)14-10(8)5-12(21)19(14,24)6-20/h10-15,21,24H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18+,19+/m0/s1

InChI Key

VPRUEYOIZZTFET-ONCJGSTBSA-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 glastifolia	LOTUS Database	35616633
Centaurea solstitialis	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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.7	ChemAxon
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.48 m³·mol⁻¹	ChemAxon
Polarizability	38.79 Å³	ChemAxon
Number of Rings	4	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

C00020445

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101285196

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate (NP0308752)

MOL for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

3D MOL for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

3D SDF for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

3D-SDF for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

PDB for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

3D PDB for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

SMILES for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

INCHI for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

Structure for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)

3D Structure for NP0308752 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-methyloxirane-2-carboxylate)