NP-MRD: Showing NP-Card for 1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+ (NP0032485)

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Record Information

Version

2.0

Created at

2021-06-19 23:16:31 UTC

Updated at

2021-06-30 00:01:42 UTC

NP-MRD ID

NP0032485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+

Provided By

JEOL Database JEOL Logo

Description

CHEMBL463399 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. 1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+ is found in Thapsia nitida var. meridionalis. 1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+ was first documented in 2006 (Rubal, J. J., et al.). Based on a literature review very few articles have been published on CHEMBL463399.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101163D          

 50 52  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101163D          

 50 52  0  0  0  0            999 V2000
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    4.4966    0.0337   -5.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7800   -0.5212   -3.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121    1.2056   -3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2407    0.7871   -1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
  3  4  1  0  0  0  0
 20 21  1  0  0  0  0
 19  6  1  0  0  0  0
  8  9  2  0  0  0  0
 24 23  1  0  0  0  0
 19 43  1  6  0  0  0
 23 22  1  0  0  0  0
 24 50  1  1  0  0  0
 22 20  2  0  0  0  0
 10 11  1  0  0  0  0
 20 19  1  0  0  0  0
 10 12  1  1  0  0  0
  5  6  1  0  0  0  0
 12 13  1  0  0  0  0
  4  5  1  0  0  0  0
 13 15  1  0  0  0  0
 19 24  1  0  0  0  0
 15 17  2  0  0  0  0
 13 14  2  0  0  0  0
  2  3  1  0  0  0  0
 17 18  1  0  0  0  0
 24  2  1  0  0  0  0
 15 16  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  2  3  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 22 47  1  0  0  0  0
  5 31  1  6  0  0  0
  6 32  1  6  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032485

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C([H])([H])C([H])([H])[C@]2([H])[C@@]([H])(OC(=O)[C@]2(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H])[C@]2([H])C(=C([H])C([H])([H])[C@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-6-11(2)18(21)24-20(5)15-10-8-12(3)14-9-7-13(4)16(14)17(15)23-19(20)22/h6-7,14-17H,3,8-10H2,1-2,4-5H3/b11-6-/t14-,15-,16-,17-,20+/m1/s1

> <INCHI_KEY>
YGNYCUFHEGMVJO-OFKSMTQWSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.466150002983866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,6aS,9aS,9bS)-3,9-dimethyl-6-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
4.148874491333334

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.777429624683279

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
92.6025

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,6aS,9aS,9bS)-3,9-dimethyl-6-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    4.4661   -2.4791   -1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0525   -1.3266   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5699   -1.3108    0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3813   -0.3758    0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844   -0.6292   -0.5503 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4137   -0.5805   -2.0697 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1533   -0.1449   -2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075    0.2959   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433    0.6846   -1.9001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0143    0.3045   -0.3162 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3606    1.7679   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -0.0877    0.8136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545   -1.2126    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534   -1.9881   -0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4610   -1.3464    1.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -1.6892    1.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.1899    3.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6786   -0.9321    3.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5592    0.3064   -2.6194 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7959    0.1572   -4.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6899    0.1605   -5.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0986    0.0998   -4.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9635    0.2055   -3.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9800    0.0115   -2.0370 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4849   -3.4074   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7814   -2.5464   -2.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926   -2.3223    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996   -0.9908    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600   -0.4988    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214    0.6625    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673   -1.6569   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -1.6063   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    2.3898    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    2.1933   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    1.8781    0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302   -1.7223    2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2808   -0.9412    0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187   -2.6699    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -1.2894    3.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952   -1.1521    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -1.5732    4.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5819    0.1096    3.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3100    1.3620   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0813   -0.7439   -5.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    1.0374   -4.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    0.1947   -6.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4966    0.0337   -5.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7800   -0.5212   -3.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121    1.2056   -3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2407    0.7871   -1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8 10  1  0
  5 10  1  0
  3  4  1  0
 20 21  1  0
 19  6  1  0
  8  9  2  0
 24 23  1  0
 19 43  1  6
 23 22  1  0
 24 50  1  1
 22 20  2  0
 10 11  1  0
 20 19  1  0
 10 12  1  1
  5  6  1  0
 12 13  1  0
  4  5  1  0
 13 15  1  0
 19 24  1  0
 15 17  2  0
 13 14  2  0
  2  3  1  0
 17 18  1  0
 24  2  1  0
 15 16  1  0
  6  7  1  0
  2  1  2  3
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
 23 48  1  0
 23 49  1  0
 22 47  1  0
  5 31  1  6
  6 32  1  6
 21 44  1  0
 21 45  1  0
 21 46  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
  1 25  1  0
  1 26  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       4.466  -2.479  -1.861  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.053  -1.327  -1.306  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.570  -1.311   0.128  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.381  -0.376   0.373  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.184  -0.629  -0.550  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.414  -0.581  -2.070  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.153  -0.145  -2.628  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.708   0.296  -1.671  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.843   0.685  -1.900  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.014   0.305  -0.316  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.361   1.768  -0.040  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.806  -0.088   0.814  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.555  -1.213   0.702  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.553  -1.988  -0.240  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.461  -1.346   1.871  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.874  -1.689   1.502  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.063  -1.190   3.149  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.679  -0.932   3.653  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.559   0.306  -2.619  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.796   0.157  -4.115  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.690   0.161  -5.116  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.099   0.100  -4.418  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.963   0.206  -3.212  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.980   0.012  -2.037  0.00  0.00           C+0
HETATM   25  H   UNK     0       4.485  -3.407  -1.297  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.781  -2.546  -2.898  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.293  -2.322   0.450  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.400  -0.991   0.770  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.060  -0.499   1.415  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.721   0.663   0.293  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.867  -1.657  -0.327  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.556  -1.606  -2.435  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.542   2.390   0.008  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.007   2.193  -0.812  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.849   1.878   0.935  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.530  -1.722   2.378  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.281  -0.941   0.813  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.919  -2.670   1.017  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.811  -1.289   3.935  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.095  -1.152   2.914  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.482  -1.573   4.519  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.582   0.110   3.972  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.310   1.362  -2.452  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.081  -0.744  -5.025  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.050   1.037  -4.976  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.076   0.195  -6.140  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.497   0.034  -5.422  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.780  -0.521  -3.227  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.412   1.206  -3.179  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.241   0.787  -1.304  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    3   24    1                                                  
CONECT    3    4    2   27   28                                             
CONECT    4    3    5   29   30                                             
CONECT    5   10    6    4   31                                             
CONECT    6   19    5    7   32                                             
CONECT    7    8    6                                                       
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11   12                                             
CONECT   11   10   33   34   35                                             
CONECT   12   10   13                                                       
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   17   16                                                  
CONECT   16   15   36   37   38                                             
CONECT   17   15   18   39                                                  
CONECT   18   17   40   41   42                                             
CONECT   19    6   43   20   24                                             
CONECT   20   21   22   19                                                  
CONECT   21   20   44   45   46                                             
CONECT   22   23   20   47                                                  
CONECT   23   24   22   48   49                                             
CONECT   24   23   50   19    2                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    4.4661   -2.4791   -1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0525   -1.3266   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5699   -1.3108    0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3813   -0.3758    0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844   -0.6292   -0.5503 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4137   -0.5805   -2.0697 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1533   -0.1449   -2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075    0.2959   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433    0.6846   -1.9001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0143    0.3045   -0.3162 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3606    1.7679   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -0.0877    0.8136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545   -1.2126    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534   -1.9881   -0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4610   -1.3464    1.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -1.6892    1.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.1899    3.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6786   -0.9321    3.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5592    0.3064   -2.6194 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7959    0.1572   -4.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6899    0.1605   -5.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0986    0.0998   -4.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9635    0.2055   -3.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9800    0.0115   -2.0370 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4849   -3.4074   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7814   -2.5464   -2.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926   -2.3223    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996   -0.9908    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600   -0.4988    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214    0.6625    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673   -1.6569   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -1.6063   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    2.3898    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    2.1933   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    1.8781    0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302   -1.7223    2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2808   -0.9412    0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187   -2.6699    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -1.2894    3.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952   -1.1521    2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -1.5732    4.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5819    0.1096    3.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3100    1.3620   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0813   -0.7439   -5.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    1.0374   -4.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    0.1947   -6.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4966    0.0337   -5.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7800   -0.5212   -3.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121    1.2056   -3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2407    0.7871   -1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8 10  1  0
  5 10  1  0
  3  4  1  0
 20 21  1  0
 19  6  1  0
  8  9  2  0
 24 23  1  0
 19 43  1  6
 23 22  1  0
 24 50  1  1
 22 20  2  0
 10 11  1  0
 20 19  1  0
 10 12  1  1
  5  6  1  0
 12 13  1  0
  4  5  1  0
 13 15  1  0
 19 24  1  0
 15 17  2  0
 13 14  2  0
  2  3  1  0
 17 18  1  0
 24  2  1  0
 15 16  1  0
  6  7  1  0
  2  1  2  3
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
 23 48  1  0
 23 49  1  0
 22 47  1  0
  5 31  1  6
  6 32  1  6
 21 44  1  0
 21 45  1  0
 21 46  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
  1 25  1  0
  1 26  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(3S,3aR,6aS,9aS,9bS)-3,9-dimethyl-6-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3S,3aR,6aS,9aS,9bS)-3,9-dimethyl-6-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C([H])([H])C([H])([H])[C@]2([H])[C@@]([H])(OC(=O)[C@]2(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H])[C@]2([H])C(=C([H])C([H])([H])[C@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H26O4/c1-6-11(2)18(21)24-20(5)15-10-8-12(3)14-9-7-13(4)16(14)17(15)23-19(20)22/h6-7,14-17H,3,8-10H2,1-2,4-5H3/b11-6-/t14-,15-,16-,17-,20+/m1/s1

InChI Key

YGNYCUFHEGMVJO-OFKSMTQWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Thapsia nitida var. meridionalis.	JEOL database	Rubal, J. J., et al, J. Nat. Prod. 69, 1566 (2006)

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
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	4.67	ALOGPS
logP	4.15	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.6 m³·mol⁻¹	ChemAxon
Polarizability	36.47 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

10167938

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11995471

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rubal, J. J., et al. (2006). Rubal, J. J., et al, J. Nat. Prod. 69, 1566 (2006) . J. Nat. Prod..

Showing NP-Card for 1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+ (NP0032485)

MOL for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

3D MOL for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

3D SDF for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

3D-SDF for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

PDB for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

3D PDB for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

SMILES for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

INCHI for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

Structure for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)

3D Structure for NP0032485 (1betaH,5betaH,6alphaH,7alphaH-11alphaangeloyloxyguaia-3(4),10(14)-dien-6,+)