NP-MRD: Showing NP-Card for [(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid (NP0280085)

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Record Information

Version

1.0

Created at

2022-09-09 05:42:09 UTC

Updated at

2022-09-09 05:42:09 UTC

NP-MRD ID

NP0280085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid

Description

2-[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]acetic acid 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. [(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid is found in Centaurea solstitialis. Based on a literature review very few articles have been published on 2-[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207422D          

 24 26  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  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  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
    4.1204   -0.8625    0.0000 O   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
    4.9527    0.1811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7757    0.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3294    0.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822    1.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    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
    1.4560   -1.4569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676   -0.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3986    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249    0.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    0.8327    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
    2.3265    0.4710    0.0000 C   0  0  1  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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 24 23  1  1  0  0  0
  2 24  1  0  0  0  0
 14 24  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
   -0.0508    2.7929   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    1.4836   -1.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    0.9845   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856    0.2493   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    0.3369    0.2530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7844   -0.7118    0.5544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1888   -1.2232    1.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466   -1.1059    1.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -1.8791    2.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591    0.0964    1.1862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0847    1.1521    2.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920   -0.0558    0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -1.0618   -0.4263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -0.1276    0.6551 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6019   -1.2213    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -2.1760    1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -1.1090   -0.4928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6425   -2.3587   -1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8936   -0.6720   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9526    0.5921    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4969    0.5741    1.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735    1.7417    0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8197   -0.1252   -1.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355    0.7405   -0.4422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7984    3.4332   -1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    3.2385   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6218    1.8307   -2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7023    0.3463   -2.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501   -0.8219   -1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1808    0.6841   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    1.3161    0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349   -1.5601   -0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764    1.9843    1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5700    0.9354    0.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0304   -0.2915    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6295   -1.8986    0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.3785    1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888   -2.1933    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589   -2.9485    1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866   -2.8101   -0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817   -1.4415    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.6157   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    2.2348    0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1408   -0.6961   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451    0.4840   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7654    1.4946   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 10  1  0
 10 11  1  1
 10  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 24  1  0
 24 23  1  0
 23 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 17 15  1  0
 15 16  2  3
 15 14  1  0
 14  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6  5  1  0
 14 24  1  0
 13 36  1  0
 12 34  1  0
 12 35  1  0
 11 33  1  0
  5 31  1  6
  4 29  1  0
  4 30  1  0
  3 27  1  0
  3 28  1  0
  1 25  1  0
  1 26  1  0
 24 46  1  1
 23 44  1  0
 23 45  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 22 43  1  0
 16 38  1  0
 16 39  1  0
 14 37  1  1
  6 32  1  6
M  END


  Mrv1652309092207422D          

 24 26  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  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  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
    4.1204   -0.8625    0.0000 O   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
    4.9527    0.1811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7757    0.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3294    0.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822    1.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    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
    1.4560   -1.4569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676   -0.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3986    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249    0.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    0.8327    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
    2.3265    0.4710    0.0000 C   0  0  1  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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 24 23  1  1  0  0  0
  2 24  1  0  0  0  0
 14 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@]1(O)[C@@H]2CCC(=C)[C@@H]3C[C@@](O)(CC(O)=O)C(=C)[C@@H]3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O7/c1-8-3-4-11-14(24-15(21)17(11,23)7-18)13-9(2)16(22,5-10(8)13)6-12(19)20/h10-11,13-14,18,22-23H,1-7H2,(H,19,20)/t10-,11+,13-,14-,16+,17-/m0/s1

> <INCHI_KEY>
OXUUEDHJHFWUCB-KPSPPPMPSA-N

> <FORMULA>
C17H22O7

> <MOLECULAR_WEIGHT>
338.356

> <EXACT_MASS>
338.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.74536872060329

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]acetic acid

> <JCHEM_LOGP>
-0.6450853483333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.36068044828895

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.121689129517791

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1827437790486357

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
81.43299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3aH-azuleno[4,5-b]furan-8-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.781   0.446   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.948   1.708   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.113   3.002   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.996  -3.052   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.718  -2.720   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.433  -1.108   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.744   0.269   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.793   0.361   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.592   1.554   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    6   15   24                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24                                                       
CONECT   24   23    2   14                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

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Synonyms

Value	Source
2-[(3R,3AR,6ar,8R,9ar,9BR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]acetate	Generator

Chemical Formula

C₁₇H₂₂O₇

Average Mass

338.3560 Da

Monoisotopic Mass

338.13655 Da

IUPAC Name

2-[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]acetic acid

Traditional Name

[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3aH-azuleno[4,5-b]furan-8-yl]acetic acid

CAS Registry Number

Not Available

SMILES

OC[C@]1(O)[C@@H]2CCC(=C)[C@@H]3C[C@@](O)(CC(O)=O)C(=C)[C@@H]3[C@H]2OC1=O

InChI Identifier

InChI=1S/C17H22O7/c1-8-3-4-11-14(24-15(21)17(11,23)7-18)13-9(2)16(22,5-10(8)13)6-12(19)20/h10-11,13-14,18,22-23H,1-7H2,(H,19,20)/t10-,11+,13-,14-,16+,17-/m0/s1

InChI Key

OXUUEDHJHFWUCB-KPSPPPMPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Centaurea solstitialis	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
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	-0.65	ChemAxon
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.43 m³·mol⁻¹	ChemAxon
Polarizability	33.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

101626736

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid (NP0280085)

MOL for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

3D MOL for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

3D SDF for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

3D-SDF for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

PDB for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

3D PDB for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

SMILES for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

INCHI for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

Structure for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)

3D Structure for NP0280085 ([(3r,3ar,6ar,8r,9ar,9br)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl]acetic acid)