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 (2e)-2-(hydroxymethyl)but-2-enoate (NP0152528)

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Record Information

Version

2.0

Created at

2022-09-02 09:01:53 UTC

Updated at

2022-09-02 09:01:53 UTC

NP-MRD ID

NP0152528

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 (2e)-2-(hydroxymethyl)but-2-enoate

Description

(3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-Decahydro-3,6-bismethylene-4beta-[[(E)-2-(hydroxymethyl)-2-butenoyl]oxy]-8alpha,9beta-dihydroxy-9-(chloromethyl)azuleno[4,5-b]furan-2(3H)-one 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 (2e)-2-(hydroxymethyl)but-2-enoate is found in Centaurea scoparia. Based on a literature review very few articles have been published on (3aR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-Decahydro-3,6-bismethylene-4beta-[[(E)-2-(hydroxymethyl)-2-butenoyl]oxy]-8alpha,9beta-dihydroxy-9-(chloromethyl)azuleno[4,5-b]furan-2(3H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211012D          

 28 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  0  0  0  0  0  0  0  0  0  0
    5.9317    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768    3.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0408    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6858    4.4500    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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 13 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
   -0.8351   -0.8486   -3.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1628   -1.0539   -1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1002   -1.7062   -1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707   -0.6110   -0.2178 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7866   -0.8453    0.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.0526   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    0.9282   -0.9053 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390   -0.3445    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5186   -1.3513    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8405   -1.7489    1.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2916    0.5761   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5338    0.2297    0.3203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815   -0.3275    0.8929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1360    0.5100    1.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1796    0.2179    2.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677    1.7521    1.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724    2.8441    2.4715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698    1.4578    1.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073    0.5364    0.3275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7286   -0.3313   -0.1111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5190   -0.5971   -1.6036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8559    0.7611   -2.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952    1.4410   -1.1880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1622    2.5496   -0.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    0.3612   -0.2037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9457   -0.5422   -0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6388    0.8099    1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9222   -0.5638    2.2043 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -0.3863   -3.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1617   -1.1653   -3.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978   -2.5553   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7198   -2.0521   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5049    0.3141   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6567   -1.9842    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2314   -0.9402    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7284   -2.6216    2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5932   -1.9819    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3695    0.5729   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0989    1.6259    0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2229    0.1296   -0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -1.2375    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6658   -0.7334    2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5898    0.8737    3.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824    1.1192   -0.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7723   -1.2680    0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2609   -1.3712   -1.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4208    0.5669   -3.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9698    1.3547   -2.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7237    1.7934   -1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921    3.0888   -0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267   -0.0303   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6863    1.1751    0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1550    1.6620    1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  2  0
  8 11  1  0
 11 12  1  0
  8  6  1  0
  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 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 25 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 14  1  0
 14 15  2  3
 14 13  1  0
 13  4  1  0
 20 21  1  0
 13 19  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  9 34  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
  4 33  1  6
  3 31  1  0
  3 32  1  0
  1 29  1  0
  1 30  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  6
 24 50  1  0
 26 51  1  0
 27 52  1  0
 27 53  1  0
 20 45  1  1
 19 44  1  6
 15 42  1  0
 15 43  1  0
 13 41  1  1
M  END


  Mrv1652309022211012D          

 28 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  0  0  0  0  0  0  0  0  0  0
    5.9317    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768    3.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0408    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6858    4.4500    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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 13 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/CO)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/C20H25ClO7/c1-4-11(7-22)19(25)27-13-5-9(2)12-6-14(23)20(26,8-21)16(12)17-15(13)10(3)18(24)28-17/h4,12-17,22-23,26H,2-3,5-8H2,1H3/b11-4+/t12-,13-,14-,15+,16-,17-,20+/m0/s1

> <INCHI_KEY>
NTJXRKLCTXJGGS-XJDQSTAGSA-N

> <FORMULA>
C20H25ClO7

> <MOLECULAR_WEIGHT>
412.86

> <EXACT_MASS>
412.1288808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.81170428276834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <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 (2E)-2-(hydroxymethyl)but-2-enoate

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
0.8910793606666658

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.51535090973071

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.794415074258335

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8485411075815996

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
100.98559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <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 (2E)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-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      11.073   5.261   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.277   6.221   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.410   7.347   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.614   8.307   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.218  -3.132   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.634  -2.601   0.000  0.00  0.00           C+0
HETATM   28 Cl   UNK     0       5.366  -4.117   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
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                                                            
CONECT   13    4   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   20   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-decahydro-3,6-bismethylene-4b-[[(e)-2-(hydroxymethyl)-2-butenoyl]oxy]-8a,9b-dihydroxy-9-(chloromethyl)azuleno[4,5-b]furan-2(3H)-one	Generator
(3AR)-3abeta,4,5,6,6abeta,7,8,9,9abeta,9balpha-decahydro-3,6-bismethylene-4β-[[(e)-2-(hydroxymethyl)-2-butenoyl]oxy]-8α,9β-dihydroxy-9-(chloromethyl)azuleno[4,5-b]furan-2(3H)-one	Generator

Chemical Formula

C₂₀H₂₅ClO₇

Average Mass

412.8600 Da

Monoisotopic Mass

412.12888 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 (2E)-2-(hydroxymethyl)but-2-enoate

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 (2E)-2-(hydroxymethyl)but-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/CO)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/C20H25ClO7/c1-4-11(7-22)19(25)27-13-5-9(2)12-6-14(23)20(26,8-21)16(12)17-15(13)10(3)18(24)28-17/h4,12-17,22-23,26H,2-3,5-8H2,1H3/b11-4+/t12-,13-,14-,15+,16-,17-,20+/m0/s1

InChI Key

NTJXRKLCTXJGGS-XJDQSTAGSA-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 scoparia	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
Sesquiterpenoid
Guaiane sesquiterpenoid
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Gamma butyrolactone
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Secondary alcohol
Halohydrin
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Alkyl halide
Organooxygen compound
Organic oxygen compound
Organohalogen compound
Organochloride
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	1.06	ALOGPS
logP	0.89	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.79	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.99 m³·mol⁻¹	ChemAxon
Polarizability	40.81 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

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

100927641

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 (2e)-2-(hydroxymethyl)but-2-enoate (NP0152528)

MOL for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D MOL for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D SDF for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D-SDF for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

PDB for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D PDB for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

SMILES for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

INCHI for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

Structure for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D Structure for NP0152528 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate)