NP-MRD: Showing NP-Card for ambuic acid (NP0031363)

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Record Information

Version

2.0

Created at

2021-06-19 22:27:52 UTC

Updated at

2021-06-29 23:59:53 UTC

NP-MRD ID

NP0031363

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ambuic acid

Provided By

JEOL Database JEOL Logo

Description

Ambuic acid, also known as ambuate, belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. ambuic acid is found in Monochaetia sp., Pestaloriopsis spp., Pestalotiopsis microspora and Pestalotiopsis spp.,. ambuic acid was first documented in 2016 (PMID: 27645625). Based on a literature review a small amount of articles have been published on Ambuic acid (PMID: 28463686) (PMID: 32598250) (PMID: 30116402) (PMID: 28607020).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100273D          

 51 52  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306202100273D          

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    2.4233   -4.0723   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -4.7117    1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170   -3.9364    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -5.6825    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255   -4.5848   -2.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
 16 17  1  6  0  0  0
  8  7  1  0  0  0  0
 17 18  1  0  0  0  0
  8  9  2  0  0  0  0
 18 19  2  0  0  0  0
  7  6  2  0  0  0  0
 19 21  1  0  0  0  0
  8 24  1  0  0  0  0
 21 23  1  0  0  0  0
  6  5  1  0  0  0  0
 24 25  2  0  0  0  0
  9 12  1  0  0  0  0
 19 20  1  0  0  0  0
  5  4  1  0  0  0  0
 21 22  2  0  0  0  0
 12 14  1  0  0  0  0
 12 13  1  0  0  0  0
  4  3  1  0  0  0  0
  9 10  1  0  0  0  0
 14 16  1  0  0  0  0
 10 11  1  0  0  0  0
  3  2  1  0  0  0  0
 16 15  1  0  0  0  0
 14 15  1  0  0  0  0
 16 24  1  0  0  0  0
 14 44  1  6  0  0  0
 12 42  1  6  0  0  0
  7 38  1  0  0  0  0
  6 37  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  2 29  1  0  0  0  0
  2 30  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 18 47  1  0  0  0  0
 23 51  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
 13 43  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 11 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031363

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C(/[H])C([H])([H])[C@@]12O[C@]1([H])[C@]([H])(O[H])C(=C(\C([H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C2=O)C([H])([H])O[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-3-4-5-6-7-8-13-14(11-20)15(21)17-19(25-17,16(13)22)10-9-12(2)18(23)24/h7-9,15,17,20-21H,3-6,10-11H2,1-2H3,(H,23,24)/b8-7+,12-9+/t15-,17-,19+/m1/s1

> <INCHI_KEY>
UDSQZJMGPSRCEM-HDKVZZTHSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.411

> <EXACT_MASS>
350.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.718949067186614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-4-[(1R,5R,6R)-3-[(1E)-hept-1-en-1-yl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.3639444146666664

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.355863589591046

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.118201088287809

> <JCHEM_PKA_STRONGEST_BASIC>
-2.79458054131322

> <JCHEM_POLAR_SURFACE_AREA>
107.36000000000001

> <JCHEM_REFRACTIVITY>
94.58329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1R,5R,6R)-3-[(1E)-hept-1-en-1-yl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
   -3.0553   -2.0070   -3.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214   -1.6868   -2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370   -0.6942   -1.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -0.3572   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048    0.6838    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    0.1890    0.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299   -0.1406    1.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530   -0.7227    1.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.1030    1.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5896    1.3174    1.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495    2.0217    1.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659   -0.7894    1.7594 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5836   -0.2789    2.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419   -2.2835    1.8237 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6230   -2.8983    3.1048 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5368   -2.9582    2.1650 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2786   -4.3254    1.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -4.2710    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3972   -4.4371   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454   -4.7062    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820   -4.2968   -1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198   -3.8546   -2.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569   -4.7197   -1.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821   -2.1103    2.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -2.5545    3.2438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849   -1.1059   -4.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.4347   -3.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7610   -2.7313   -4.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -2.6142   -1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367   -1.2745   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4164    0.2253   -2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300   -1.1255   -1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.2742    0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8476    0.0342   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842    1.5976   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3313    0.9656    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    0.0753   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728   -0.0898    2.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9133    1.3365    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    1.8591    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    2.9612    1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4423   -0.5278    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269    0.6884    2.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593   -2.7557    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435   -4.8964    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -4.8967    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233   -4.0723   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -4.7117    1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170   -3.9364    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -5.6825    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255   -4.5848   -2.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
 16 17  1  6
  8  7  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
  7  6  2  0
 19 21  1  0
  8 24  1  0
 21 23  1  0
  6  5  1  0
 24 25  2  0
  9 12  1  0
 19 20  1  0
  5  4  1  0
 21 22  2  0
 12 14  1  0
 12 13  1  0
  4  3  1  0
  9 10  1  0
 14 16  1  0
 10 11  1  0
  3  2  1  0
 16 15  1  0
 14 15  1  0
 16 24  1  0
 14 44  1  6
 12 42  1  6
  7 38  1  0
  6 37  1  0
  5 35  1  0
  5 36  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
  2 29  1  0
  2 30  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 23 51  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 13 43  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.055  -2.007  -3.708  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.421  -1.687  -2.267  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.437  -0.694  -1.648  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.823  -0.357  -0.204  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.905   0.684   0.447  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.498   0.189   0.625  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.030  -0.141   1.816  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.353  -0.723   1.974  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.515  -0.103   1.658  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.590   1.317   1.159  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.550   2.022   1.943  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.866  -0.789   1.759  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.584  -0.279   2.875  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.842  -2.284   1.824  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.623  -2.898   3.105  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.537  -2.958   2.165  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.279  -4.325   1.588  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.690  -4.271   0.201  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.397  -4.437  -0.147  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.745  -4.706   0.785  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.082  -4.297  -1.592  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.820  -3.855  -2.455  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.157  -4.720  -1.889  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.382  -2.110   2.550  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.474  -2.555   3.244  0.00  0.00           O+0
HETATM   26  H   UNK     0      -3.085  -1.106  -4.329  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.050  -2.435  -3.773  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.761  -2.731  -4.126  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.430  -2.614  -1.683  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.437  -1.274  -2.238  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.416   0.225  -2.245  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.430  -1.125  -1.680  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.828  -1.274   0.399  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.848   0.034  -0.191  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.884   1.598  -0.159  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.331   0.966   1.418  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.093   0.075  -0.282  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.573  -0.090   2.722  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.913   1.337   0.114  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.645   1.859   1.242  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.471   2.961   1.697  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.442  -0.528   0.863  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.427   0.688   2.874  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.559  -2.756   1.168  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.644  -4.896   2.273  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.215  -4.897   1.528  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.423  -4.072  -0.582  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.451  -4.712   1.836  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.517  -3.936   0.674  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.193  -5.683   0.571  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.226  -4.585  -2.856  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3   29   30                                             
CONECT    3    4    2   31   32                                             
CONECT    4    5    3   33   34                                             
CONECT    5    6    4   35   36                                             
CONECT    6    7    5   37                                                  
CONECT    7    8    6   38                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   12   10                                                  
CONECT   10    9   11   39   40                                             
CONECT   11   10   41                                                       
CONECT   12    9   14   13   42                                             
CONECT   13   12   43                                                       
CONECT   14   12   16   15   44                                             
CONECT   15   16   14                                                       
CONECT   16   17   14   15   24                                             
CONECT   17   16   18   45   46                                             
CONECT   18   17   19   47                                                  
CONECT   19   18   21   20                                                  
CONECT   20   19   48   49   50                                             
CONECT   21   19   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   51                                                       
CONECT   24    8   25   16                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   23                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  104    0
END

RDKit          3D

51 52  0  0  0  0  0  0  0  0999 V2000
   -3.0553   -2.0070   -3.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214   -1.6868   -2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370   -0.6942   -1.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -0.3572   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048    0.6838    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    0.1890    0.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299   -0.1406    1.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530   -0.7227    1.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.1030    1.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5896    1.3174    1.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495    2.0217    1.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659   -0.7894    1.7594 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5836   -0.2789    2.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419   -2.2835    1.8237 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6230   -2.8983    3.1048 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5368   -2.9582    2.1650 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2786   -4.3254    1.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -4.2710    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3972   -4.4371   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454   -4.7062    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820   -4.2968   -1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8198   -3.8546   -2.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569   -4.7197   -1.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821   -2.1103    2.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -2.5545    3.2438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849   -1.1059   -4.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.4347   -3.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7610   -2.7313   -4.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -2.6142   -1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367   -1.2745   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4164    0.2253   -2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300   -1.1255   -1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.2742    0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8476    0.0342   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842    1.5976   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3313    0.9656    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    0.0753   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728   -0.0898    2.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9133    1.3365    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    1.8591    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    2.9612    1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4423   -0.5278    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269    0.6884    2.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593   -2.7557    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435   -4.8964    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -4.8967    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233   -4.0723   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -4.7117    1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170   -3.9364    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -5.6825    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255   -4.5848   -2.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
 16 17  1  6
  8  7  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
  7  6  2  0
 19 21  1  0
  8 24  1  0
 21 23  1  0
  6  5  1  0
 24 25  2  0
  9 12  1  0
 19 20  1  0
  5  4  1  0
 21 22  2  0
 12 14  1  0
 12 13  1  0
  4  3  1  0
  9 10  1  0
 14 16  1  0
 10 11  1  0
  3  2  1  0
 16 15  1  0
 14 15  1  0
 16 24  1  0
 14 44  1  6
 12 42  1  6
  7 38  1  0
  6 37  1  0
  5 35  1  0
  5 36  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
  2 29  1  0
  2 30  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 23 51  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 13 43  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
M  END

View in JSmol

Synonyms

Value	Source
Ambuate	Generator

Chemical Formula

C₁₉H₂₆O₆

Average Mass

350.4110 Da

Monoisotopic Mass

350.17294 Da

IUPAC Name

(2E)-4-[(1R,5R,6R)-3-[(1E)-hept-1-en-1-yl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid

Traditional Name

(2E)-4-[(1R,5R,6R)-3-[(1E)-hept-1-en-1-yl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(=C(/[H])C([H])([H])[C@@]12O[C@]1([H])[C@]([H])(O[H])C(=C(\C([H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C2=O)C([H])([H])O[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C19H26O6/c1-3-4-5-6-7-8-13-14(11-20)15(21)17-19(25-17,16(13)22)10-9-12(2)18(23)24/h7-9,15,17,20-21H,3-6,10-11H2,1-2H3,(H,23,24)/b8-7+,12-9+/t15-,17-,19+/m1/s1

InChI Key

UDSQZJMGPSRCEM-HDKVZZTHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Monochaetia sp.	Fungi	KNApSAcK
Pestaloriopsis spp.	-	KNApSAcK
Pestalotiopsis microspora	LOTUS Database	35616633
Pestalotiopsis sp.	JEOL database	Li, J. Y., et al, Phytochemistry 56, 463 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Branched fatty acid
Heterocyclic fatty acid
Cyclohexenone
Hydroxy fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Unsaturated fatty acid
Ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
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	2.14	ALOGPS
logP	2.36	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	94.58 m³·mol⁻¹	ChemAxon
Polarizability	36.72 Å³	ChemAxon
Number of Rings	2	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

9327398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11152290

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li CS, Yang BJ, Turkson J, Cao S: Anti-proliferative ambuic acid derivatives from Hawaiian endophytic fungus Pestalotiopsis sp. FT172. Phytochemistry. 2017 Aug;140:77-82. doi: 10.1016/j.phytochem.2017.04.017. [PubMed:28463686 ]
Apriyanti E, Satari MH, Kurnia D: Potential of MurA Enzyme and GBAP in Fsr Quorum Sensing System as Antibacterial Drugs Target: In vitro and In silico Study of Antibacterial Compounds from Myrmecodia pendans. Comb Chem High Throughput Screen. 2021;24(1):109-118. doi: 10.2174/1386207323666200628111348. [PubMed:32598250 ]
Zhang Q, Luan R, Li H, Liu Y, Liu P, Wang L, Li D, Wang M, Zou Q, Liu H, Matsuzaki K, Zhao F: Anti-inflammatory action of ambuic acid, a natural product isolated from the solid culture of Pestalotiopsis neglecta, through blocking ERK/JNK mitogen-activated protein kinase signaling pathway. Exp Ther Med. 2018 Aug;16(2):1538-1546. doi: 10.3892/etm.2018.6294. Epub 2018 Jun 12. [PubMed:30116402 ]
Todd DA, Parlet CP, Crosby HA, Malone CL, Heilmann KP, Horswill AR, Cech NB: Signal Biosynthesis Inhibition with Ambuic Acid as a Strategy To Target Antibiotic-Resistant Infections. Antimicrob Agents Chemother. 2017 Jul 25;61(8). pii: AAC.00263-17. doi: 10.1128/AAC.00263-17. Print 2017 Aug. [PubMed:28607020 ]
Li J, Xie J, Yu FX, Chen YH, Zhao PJ: Pestalotic acids A-I, antibacterial ambuic acid analogues, from a mycoparasite (Pestalotipsis sp. cr014) of Cronartium ribicola. Arch Pharm Res. 2016 Sep 19. pii: 10.1007/s12272-016-0837-2. doi: 10.1007/s12272-016-0837-2. [PubMed:27645625 ]
Li, J. Y., et al. (2001). Li, J. Y., et al, Phytochemistry 56, 463 (2001) . Phytochem..

Showing NP-Card for ambuic acid (NP0031363)

MOL for NP0031363 (ambuic acid)

3D MOL for NP0031363 (ambuic acid)

3D SDF for NP0031363 (ambuic acid)

3D-SDF for NP0031363 (ambuic acid)

PDB for NP0031363 (ambuic acid)

3D PDB for NP0031363 (ambuic acid)

SMILES for NP0031363 (ambuic acid)

INCHI for NP0031363 (ambuic acid)

Structure for NP0031363 (ambuic acid)

3D Structure for NP0031363 (ambuic acid)