NP-MRD: Showing NP-Card for (3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate (NP0272722)

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Record Information

Version

2.0

Created at

2022-09-08 19:27:40 UTC

Updated at

2022-09-08 19:27:41 UTC

NP-MRD ID

NP0272722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate

Description

(3AR,4S,6aS,8S,9S,9aS,9bS)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2R)-2-(acetyloxy)-3-chloropropanoate 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,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate is found in Centaurea linifolia. Based on a literature review very few articles have been published on (3aR,4S,6aS,8S,9S,9aS,9bS)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2R)-2-(acetyloxy)-3-chloropropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221272D          

 33 35  0  0  1  0            999 V2000
    0.9879    3.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    3.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433    2.0080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7433    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    0.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288   -0.0545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856    1.1830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6856    2.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4001    2.4205    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4001    0.7705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    0.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    2.0080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    2.3659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1948    1.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    1.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8161    2.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204    2.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4919    3.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6702    3.1702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1558    3.8152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3308    3.8152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0759    4.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433    5.0848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7433    5.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    6.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856    5.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    7.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107    4.5999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9692    5.2071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2195    4.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7650    5.0556    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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  1  0  0  0
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 16 18  1  0  0  0  0
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 15 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
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 22 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
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    6.6285    2.6708    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7422    0.7126   -0.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344    0.5489   -0.6784 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5291    0.9944   -1.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587    1.4473   -1.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    0.8478   -2.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    0.9980   -4.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6137    0.4734   -2.5570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -0.1662   -1.3022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6248    0.1263   -0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7047   -0.9160    0.6936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0872   -0.6324    1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813    0.0499    0.1877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1136   -0.5764   -0.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2956    0.1355    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6396   -0.5024   -0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1925    1.3472    0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776   -0.0167   -1.0482 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.6765   -1.0961   -0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7396   -1.7004    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594    3.2774   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0202    3.0211    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6963    2.6595    0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622    1.4794   -0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2614    1.7629   -2.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893    1.5617   -0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038   -1.2356   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5715    1.1352    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824   -1.9282    0.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    0.0115    2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5956   -1.5997    1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9971    1.1335    0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3572    0.3204   -0.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5949   -1.2282   -0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 14  2  0
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  8  9  1  0
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  2  1  2  3
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 16 17  2  3
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 15  4  1  0
 22 23  1  0
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 13 42  1  0
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 13 44  1  0
  8 39  1  6
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  1 34  1  0
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 22 49  1  1
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 17 46  1  0
 17 47  1  0
 15 45  1  1
M  END


  Mrv1652309082221272D          

 33 35  0  0  1  0            999 V2000
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    0.1836    3.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433    2.0080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7433    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    0.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288   -0.0545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856    1.1830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.9692    5.2071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2195    4.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  5  6  1  0  0  0  0
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 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272722

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H27ClO10/c1-9-5-14(32-21(28)15(7-23)30-11(3)25)17-10(2)20(27)33-19(17)18-13(9)6-16(31-12(4)26)22(18,29)8-24/h13-19,24,29H,1-2,5-8H2,3-4H3/t13-,14+,15+,16+,17-,18+,19+,22+/m1/s1

> <INCHI_KEY>
BJLVRCLCTBLIIL-BAJDEKRZSA-N

> <FORMULA>
C22H27ClO10

> <MOLECULAR_WEIGHT>
486.9

> <EXACT_MASS>
486.1292748

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.35455075221604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4S,6aS,8S,9S,9aS,9bS)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2R)-2-(acetyloxy)-3-chloropropanoate

> <JCHEM_LOGP>
-0.013104256666667327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.135512045189227

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.754715776018639

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1136493705297843

> <JCHEM_POLAR_SURFACE_AREA>
145.66000000000003

> <JCHEM_REFRACTIVITY>
110.57539999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aS,8S,9S,9aS,9bS)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2R)-2-(acetyloxy)-3-chloropropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.844   6.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.343   5.918   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.416   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.387   3.748   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.387   2.208   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.054   1.438   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.054  -0.102   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.280   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.280   3.748   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       2.614   4.518   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0       2.614   1.438   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.947   2.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.281   1.438   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.947   3.748   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.775   4.416   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.097   3.626   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.235   2.093   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.257   4.640   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.758   4.297   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.651   6.056   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.118   5.918   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.157   7.122   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.617   7.122   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.142   8.586   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.387   9.492   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.387  11.032   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.054  11.802   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.280  11.032   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.054  13.342   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.633   8.586   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.676   9.720   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.143   8.282   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.161   9.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    4   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22    2   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   22   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4S,6as,8S,9S,9as,9BS)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2R)-2-(acetyloxy)-3-chloropropanoic acid	Generator

Chemical Formula

C₂₂H₂₇ClO₁₀

Average Mass

486.9000 Da

Monoisotopic Mass

486.12927 Da

IUPAC Name

(3aR,4S,6aS,8S,9S,9aS,9bS)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2R)-2-(acetyloxy)-3-chloropropanoate

Traditional Name

(3aR,4S,6aS,8S,9S,9aS,9bS)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2R)-2-(acetyloxy)-3-chloropropanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H27ClO10/c1-9-5-14(32-21(28)15(7-23)30-11(3)25)17-10(2)20(27)33-19(17)18-13(9)6-16(31-12(4)26)22(18,29)8-24/h13-19,24,29H,1-2,5-8H2,3-4H3/t13-,14+,15+,16+,17-,18+,19+,22+/m1/s1

InChI Key

BJLVRCLCTBLIIL-BAJDEKRZSA-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 linifolia	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
Tetracarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Alkyl chloride
Organooxygen compound
Primary alcohol
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	-0.013	ChemAxon
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.58 m³·mol⁻¹	ChemAxon
Polarizability	47.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

163027868

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,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate (NP0272722)

MOL for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

3D MOL for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

3D SDF for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

3D-SDF for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

PDB for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

3D PDB for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

SMILES for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

INCHI for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

Structure for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)

3D Structure for NP0272722 ((3ar,4s,6as,8s,9s,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-2-(acetyloxy)-3-chloropropanoate)