NP-MRD: Showing NP-Card for 3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate (NP0196823)

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Record Information

Version

2.0

Created at

2022-09-04 14:58:28 UTC

Updated at

2022-09-04 14:58:28 UTC

NP-MRD ID

NP0196823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate

Description

3,6,9-Trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate 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. 3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate is found in Ixeris japonica and Ixeris stolonifera. 3,6,9-Trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191521032D          

 47 51  0  0  0  0            999 V2000
    3.6470    4.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    3.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340    4.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010    2.3925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  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
    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
    5.4377   -1.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698   -2.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468   -3.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7788   -3.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1338   -2.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -3.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429   -3.9946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7208   -2.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9529   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -3.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619   -4.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831   -3.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1918   -3.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0688   -4.4206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  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
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
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 25 31  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
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 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
  9 47  1  0  0  0  0
 41 47  1  0  0  0  0
M  END

     RDKit          3D

 89 93  0  0  0  0  0  0  0  0999 V2000
    2.1008   -0.4347   -2.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2568   -0.8238   -1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8652    0.1235   -0.3518 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.4805    0.0123    0.3530 O   0  0  0  0  0  0  0  0  0  0  0  0
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 13 62  1  1
M  END


  Mrv1533004191521032D          

 47 51  0  0  0  0            999 V2000
    3.6470    4.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    3.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340    4.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010    2.3925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  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
    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
    5.4377   -1.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698   -2.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468   -3.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7788   -3.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1338   -2.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -3.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429   -3.9946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7208   -2.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9529   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -3.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619   -4.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831   -3.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3511   -3.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4601   -2.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -2.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1918   -3.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0688   -4.4206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9598   -3.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6048   -3.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0827   -2.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8507   -2.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  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
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
  9 47  1  0  0  0  0
 41 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(O)C(=O)OC1CC(=C)C2CC(OC3OC(COC(=O)CC4=CC=C(O)C=C4)C(O)C(O)C3O)C(=C)C2C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C34H42O13/c1-14(2)27(37)33(42)44-22-10-15(3)20-12-21(16(4)25(20)31-26(22)17(5)32(41)47-31)45-34-30(40)29(39)28(38)23(46-34)13-43-24(36)11-18-6-8-19(35)9-7-18/h6-9,14,20-23,25-31,34-35,37-40H,3-5,10-13H2,1-2H3

> <INCHI_KEY>
SGEAESJBAYKDCK-UHFFFAOYSA-N

> <FORMULA>
C34H42O13

> <MOLECULAR_WEIGHT>
658.697

> <EXACT_MASS>
658.262541412

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
66.90755248308687

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.7804834409999997

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.028538527549834

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.495147537574486

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490854558943226

> <JCHEM_POLAR_SURFACE_AREA>
198.51

> <JCHEM_REFRACTIVITY>
161.66840000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       6.808   7.512   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.374   6.949   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.170   7.909   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.145   5.426   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.349   4.466   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.507   5.824   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+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       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  C   UNK     0      10.150  -3.683   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.717  -4.246   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.487  -5.769   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.054  -6.331   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.850  -5.371   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.416  -5.934   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.187  -7.457   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.212  -4.974   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.779  -5.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.549  -7.059   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.116  -7.622   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.088  -6.662   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.522  -7.224   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.859  -5.139   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.575  -4.576   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.691  -6.729   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.462  -8.252   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.125  -6.166   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.329  -7.126   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.354  -4.644   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.788  -4.081   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   47                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   40                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   38                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   19   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   17   37                                                  
CONECT   37   36                                                            
CONECT   38   15   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   13   41                                                  
CONECT   41   40   42   47                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45    9   41                                                  
MASTER        0    0    0    0    0    0    0    0   47    0  102    0
END

View in JSmol

Synonyms

Value	Source
3,6,9-Trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoic acid	Generator

Chemical Formula

C₃₄H₄₂O₁₃

Average Mass

658.6970 Da

Monoisotopic Mass

658.26254 Da

IUPAC Name

3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate

Traditional Name

3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(O)C(=O)OC1CC(=C)C2CC(OC3OC(COC(=O)CC4=CC=C(O)C=C4)C(O)C(O)C3O)C(=C)C2C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C34H42O13/c1-14(2)27(37)33(42)44-22-10-15(3)20-12-21(16(4)25(20)31-26(22)17(5)32(41)47-31)45-34-30(40)29(39)28(38)23(46-34)13-43-24(36)11-18-6-8-19(35)9-7-18/h6-9,14,20-23,25-31,34-35,37-40H,3-5,10-13H2,1-2H3

InChI Key

SGEAESJBAYKDCK-UHFFFAOYSA-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
Ixeris japonica	LOTUS Database	35616633
Ixeris stolonifera A.Gray	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
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Monosaccharide
Fatty acyl
Oxane
Benzenoid
Enoate ester
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Lactone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Oxacycle
Carboxylic acid derivative
Polyol
Carbonyl group
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.4	ALOGPS
logP	1.78	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	161.67 m³·mol⁻¹	ChemAxon
Polarizability	66.91 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14733663

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate (NP0196823)

MOL for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

3D MOL for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

3D SDF for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

3D-SDF for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

PDB for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

3D PDB for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

SMILES for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

INCHI for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

Structure for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)

3D Structure for NP0196823 (3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-({[2-(4-hydroxyphenyl)acetyl]oxy}methyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-methylbutanoate)