NP-MRD: Showing NP-Card for (3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate (NP0239903)

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Record Information

Version

2.0

Created at

2022-09-06 23:35:20 UTC

Updated at

2022-09-06 23:35:20 UTC

NP-MRD ID

NP0239903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate

Description

(3AR,4S,6aR,8S,9S,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxirane]-4-yl 2-methyloxirane-2-carboxylate 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)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate is found in Rhaponticum repens, Arctotis argentea, Centaurea pterocaula, Centaurea solstitialis, Psephellus bellus and Rhaponticum canariense. Based on a literature review very few articles have been published on (3aR,4S,6aR,8S,9S,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxirane]-4-yl 2-methyloxirane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201352D          

 26 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
    5.7823    2.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    3.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0237   -1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -1.6764    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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  6  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 19 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 26  1  1  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
   -1.1094    2.4923    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    1.5808   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5935    1.4048   -1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924    0.2199   -0.1960 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3375   -0.1015   -0.3036 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -0.0210    0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7433    0.3615    1.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6628   -0.3692    0.6407 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1588   -0.8182   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    0.5694    1.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3187   -0.7978    1.7997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521   -0.9075   -0.5402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6213   -2.2313   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664   -2.7194   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800   -2.9636    0.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562   -4.0499    1.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -2.2551    0.5820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1971   -0.8803    0.2762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3762   -0.3788   -0.5246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0094    0.8472   -1.3415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2405    1.6794   -1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2288    1.1833   -0.4283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7850    2.1565    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772    0.1192    0.3299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3455   -0.8586    1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.0809    1.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1168    2.7401    0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643    3.0430    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    2.3087   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    1.0643   -2.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7840    0.5326    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2139   -0.4797   -0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1393   -1.9349   -0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4844   -0.3945   -1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5412    0.8266    1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0848    1.3117    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2451   -0.7946   -1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -2.1362   -1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890   -3.7142   -0.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0944   -0.3741    1.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256   -1.1832   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    0.5098   -2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0412    2.7642   -1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7057    1.5962   -2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812    0.6917   -0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1655    2.8430   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4247   -0.6432    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0020   -1.9203    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 11  1  0
  8  6  1  1
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 13  1  0
 13 14  2  3
 13 12  1  0
 11  8  1  0
 12  4  1  0
 19 20  1  0
 12 18  1  0
 24 26  1  1
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
  4 31  1  1
  3 29  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
 20 42  1  6
 21 43  1  0
 21 44  1  0
 22 45  1  6
 23 46  1  0
 25 47  1  0
 25 48  1  0
 19 41  1  6
 18 40  1  1
 14 38  1  0
 14 39  1  0
 12 37  1  6
M  END


  Mrv1652309072201352D          

 26 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
    5.7823    2.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    3.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0237   -1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -1.6764    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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  6  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 19 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0239903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(CO1)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)[C@@]3(CO3)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O7/c1-8-4-11(25-17(22)18(3)6-23-18)13-9(2)16(21)26-15(13)14-10(8)5-12(20)19(14)7-24-19/h10-15,20H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18?,19-/m0/s1

> <INCHI_KEY>
HQZJODBJOBTCPI-XJACDZHHSA-N

> <FORMULA>
C19H22O7

> <MOLECULAR_WEIGHT>
362.378

> <EXACT_MASS>
362.136553048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.17564798534174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR,8S,9S,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxirane]-4-yl 2-methyloxirane-2-carboxylate

> <JCHEM_LOGP>
0.5062260973333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.887716565828487

> <JCHEM_PKA_STRONGEST_BASIC>
-3.285312774106619

> <JCHEM_POLAR_SURFACE_AREA>
97.89

> <JCHEM_REFRACTIVITY>
86.91449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR,8S,9S,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxirane]-4-yl 2-methyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.665   3.341   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.435   4.864   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.001   5.426   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.639   5.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.794   4.805   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.903   7.176   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.442   7.138   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.644  -2.588   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.202  -3.129   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    8                                                       
CONECT   12    4   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   19   25   26                                             
CONECT   25   24   26                                                       
CONECT   26   25   24                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4S,6ar,8S,9S,9as,9BS)-8-hydroxy-3,6-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxirane]-4-yl 2-methyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₁₉H₂₂O₇

Average Mass

362.3780 Da

Monoisotopic Mass

362.13655 Da

IUPAC Name

(3aR,4S,6aR,8S,9S,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxirane]-4-yl 2-methyloxirane-2-carboxylate

Traditional Name

(3aR,4S,6aR,8S,9S,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxirane]-4-yl 2-methyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC1(CO1)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)[C@@]3(CO3)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H22O7/c1-8-4-11(25-17(22)18(3)6-23-18)13-9(2)16(21)26-15(13)14-10(8)5-12(20)19(14)7-24-19/h10-15,20H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18?,19-/m0/s1

InChI Key

HQZJODBJOBTCPI-XJACDZHHSA-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
Acroptilon repens	LOTUS Database	35616633
Arctotis argentea	LOTUS Database	35616633
Centaurea pterocaula	LOTUS Database	35616633
Centaurea solstitialis	LOTUS Database	35616633
Psephellus bellus	LOTUS Database	35616633
Rhaponticum canariense	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
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	0.51	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.91 m³·mol⁻¹	ChemAxon
Polarizability	36.18 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	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

4478860

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320928

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)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate (NP0239903)

MOL for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

3D MOL for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

3D SDF for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

3D-SDF for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

PDB for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

3D PDB for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

SMILES for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

INCHI for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

Structure for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)

3D Structure for NP0239903 ((3ar,4s,6ar,8s,9s,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methyloxirane-2-carboxylate)