NP-MRD: Showing NP-Card for [3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid (NP0063895)

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Record Information

Version

2.0

Created at

2022-04-28 08:13:22 UTC

Updated at

2022-04-28 08:13:22 UTC

NP-MRD ID

NP0063895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid

Description

(3AS,5R,6aR,9aR,9bS)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate 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. [3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid is found in Zinnia acerosa and Zinnia elegans. Based on a literature review very few articles have been published on (3aS,5R,6aR,9aR,9bS)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210132D          

 24 26  0  0  1  0            999 V2000
    2.0090    2.2026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4946    1.5576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6696    1.5576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1552    2.2026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3388    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    3.3648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8254    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4704    3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    4.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966    4.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    4.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966    5.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    5.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676    5.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    5.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    2.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151    0.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592    0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  4 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  3 20  1  1  0  0  0
  2 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  6  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -2.1263   -0.1979    3.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -0.3130    2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6634    0.3118    1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5052    1.0063    2.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434   -0.0093    0.0259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -0.2358   -0.2480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8696   -1.0834    0.9333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4283   -1.3489    1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570   -0.4322    0.2722 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7954   -0.4471    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4634    0.6556    1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7820    1.7074    1.2803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8338    0.5538    1.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6262   -0.7009    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497    1.6160    2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469    2.9038    2.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.7397   -1.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359   -0.7625   -1.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7620   -1.0183   -2.0876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6734   -0.0553   -3.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0503    0.4330   -3.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9524   -0.2635   -2.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2660   -0.2608   -2.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1240   -0.9554   -1.5402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7003    0.4113    3.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2551   -0.6874    3.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939    0.7551   -0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -2.0322    0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -1.3817    2.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427   -2.3933    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    0.6139    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0143   -1.5161    1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -0.9889    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4784   -0.5116    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917    1.5698    2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    2.8325    2.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426    3.6446    2.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4474    3.3193    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828   -0.5769   -1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6011   -0.9740   -2.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839   -2.0416   -2.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2444   -0.5191   -4.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350    0.8446   -2.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3678    0.2270   -4.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    1.5305   -3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8431   -0.7972   -1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7577    0.2764   -3.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646   -1.9689   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6 24  1  0
 24 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 19 17  1  0
 17 18  2  3
 17  9  1  0
  2  7  1  0
 22 24  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
  9 31  1  6
  8 29  1  0
  8 30  1  0
  7 28  1  6
  6 27  1  6
  1 25  1  0
  1 26  1  0
 24 48  1  1
 19 41  1  6
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv1652304282210132D          

 24 26  0  0  1  0            999 V2000
    2.0090    2.2026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4946    1.5576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6696    1.5576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1552    2.2026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3388    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    3.3648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8254    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4704    3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    4.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966    4.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    4.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966    5.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    5.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676    5.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    5.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    2.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151    0.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6592    0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  4 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  3 20  1  1  0  0  0
  2 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0063895

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1C[C@@H]2[C@H](OC(=O)C2=C)[C@@H]2[C@@H](CCC2=C)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-6-10(2)19(21)23-16-9-15-13(5)20(22)24-18(15)17-11(3)7-8-14(17)12(16)4/h6,14-18H,3-5,7-9H2,1-2H3/b10-6-/t14-,15-,16+,17-,18-/m0/s1

> <INCHI_KEY>
RNGMETUDLBUWQM-RIHQFTPISA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.57528942980477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5R,6aR,9aR,9bS)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
4.057381384999999

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.561991967734963

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
91.31669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5R,6aR,9aR,9bS)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.750   4.111   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.790   2.907   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.250   2.907   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290   4.111   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.632   5.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.020   6.281   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.407   5.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.611   6.573   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.020   7.821   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.354   8.591   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.687   7.821   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.354  10.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.020  10.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.686  10.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.687  10.901   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.152   3.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.437   4.419   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.083   2.032   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.287   1.072   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.402   1.622   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.638   1.622   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.097   0.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.123   2.032   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.192   3.570   0.000  0.00  0.00           C+0
CONECT    1    2    7   24                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16    4   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    3                                                       
CONECT   21    2   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23    1                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(3AS,5R,6ar,9ar,9BS)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

(3aS,5R,6aR,9aR,9bS)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3aS,5R,6aR,9aR,9bS)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-5-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1C[C@@H]2[C@H](OC(=O)C2=C)[C@@H]2[C@@H](CCC2=C)C1=C

InChI Identifier

InChI=1S/C20H24O4/c1-6-10(2)19(21)23-16-9-15-13(5)20(22)24-18(15)17-11(3)7-8-14(17)12(16)4/h6,14-18H,3-5,7-9H2,1-2H3/b10-6-/t14-,15-,16+,17-,18-/m0/s1

InChI Key

RNGMETUDLBUWQM-RIHQFTPISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Zinnia acerosa	Plant	KNApSAcK
Zinnia elegans	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
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
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	3.15	ALOGPS
logP	4.06	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-6.6	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	91.32 m³·mol⁻¹	ChemAxon
Polarizability	35.58 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

162890983

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for [3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid (NP0063895)

MOL for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

3D MOL for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

3D SDF for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

3D-SDF for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

PDB for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

3D PDB for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

SMILES for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

INCHI for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

Structure for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)

3D Structure for NP0063895 ([3aS-[3aalpha,5alpha(Z),6aalpha,9aalpha,9bbeta]]-Dodecahydro-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-5-yl ester 2-methyl-2-butenoic acid)