NP-MRD: Showing NP-Card for JBIR 22 (NP0039385)

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Record Information

Version

2.0

Created at

2021-06-20 21:49:57 UTC

Updated at

2021-06-30 00:12:41 UTC

NP-MRD ID

NP0039385

Secondary Accession Numbers

None

Natural Product Identification

Common Name

JBIR 22

Provided By

JEOL Database JEOL Logo

Description

(2S)-2-Hydroxy-2-[[(2S)-1-methyl-4-[[(1R)-2alpha-methyl-1,2,4abeta,5,6,7,8,8aalpha-octahydronaphthalene-1alpha-yl](hydroxy)methylene]-3,5-dioxopyrrolidine-2beta-yl]methyl]-3-methylbutanoic acid belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. JBIR 22 is found in Verticillium sp. f21794. JBIR 22 was first documented in 2010 (Izumikawa, M., et al.). Based on a literature review very few articles have been published on (2S)-2-Hydroxy-2-[[(2S)-1-methyl-4-[[(1R)-2alpha-methyl-1,2,4abeta,5,6,7,8,8aalpha-octahydronaphthalene-1alpha-yl](hydroxy)methylene]-3,5-dioxopyrrolidine-2beta-yl]methyl]-3-methylbutanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123493D          

 63 65  0  0  0  0            999 V2000
    1.6820   -1.9476   -5.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631   -2.1610   -5.1628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1342   -3.6186   -5.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4222   -1.7764   -3.7648 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1113   -2.7029   -2.8025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0715   -0.3068   -3.3952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8701    0.3272   -2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7371    2.5098    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064    0.1957    3.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073    0.9737    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
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 26  7  1  0  0  0  0
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  7  6  1  0  0  0  0
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M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202123493D          

 63 65  0  0  0  0            999 V2000
    1.6820   -1.9476   -5.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1113   -2.7029   -2.8025 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8701    0.3272   -2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4227   -0.2041   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3323    0.7571    2.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159    2.9975    3.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5011    2.7789    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7371    2.5098    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064    0.1957    3.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073    0.9737    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479    0.1049    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331    3.3678    3.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154    4.1187    4.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1637    1.9537    6.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0234    0.8372    4.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9944    2.5962   -3.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    2.5691   -3.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    3.7492   -2.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519   -3.5776   -2.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
 26  7  1  0  0  0  0
 13 11  1  0  0  0  0
 21 22  1  0  0  0  0
 14 15  1  0  0  0  0
 11 10  2  0  0  0  0
 20 19  1  0  0  0  0
  8  9  2  0  0  0  0
 19 18  1  0  0  0  0
 24 25  2  0  0  0  0
 23 22  1  0  0  0  0
 11 12  1  0  0  0  0
 23 18  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
  6  4  1  0  0  0  0
  8 10  1  0  0  0  0
  4  2  1  0  0  0  0
 21 20  1  0  0  0  0
  2  1  1  0  0  0  0
 10 24  1  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  1  0  0  0
 24 26  1  0  0  0  0
  4 28  1  0  0  0  0
 23 13  1  0  0  0  0
 28 30  1  0  0  0  0
 18 17  1  0  0  0  0
 28 29  2  0  0  0  0
 17 16  2  0  0  0  0
 26 27  1  0  0  0  0
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 14 13  1  0  0  0  0
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  1 31  1  0  0  0  0
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 30 63  1  0  0  0  0
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 27 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039385

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@](O[H])(C([H])([H])[C@]1([H])N(C(=O)\C(=C(\O[H])[C@]2([H])[C@@]([H])(C([H])=C([H])[C@]3([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]23[H])C([H])([H])[H])C1=O)C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO6/c1-12(2)23(30,22(28)29)11-16-19(25)18(21(27)24(16)4)20(26)17-13(3)9-10-14-7-5-6-8-15(14)17/h9-10,12-17,26,30H,5-8,11H2,1-4H3,(H,28,29)/b20-18+/t13-,14+,15-,16+,17-,23+/m1/s1

> <INCHI_KEY>
DIFKWHRMEGFLSD-DBEUHZBBSA-N

> <FORMULA>
C23H33NO6

> <MOLECULAR_WEIGHT>
419.518

> <EXACT_MASS>
419.230787787

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.68472187637593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[(2S,4E)-4-{[(1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl}-2-hydroxy-3-methylbutanoic acid

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.5475184410000002

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.838497615017291

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.517184584040857

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7658549771903539

> <JCHEM_POLAR_SURFACE_AREA>
115.14

> <JCHEM_REFRACTIVITY>
113.37049999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S,4E)-4-{[(1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl}-2-hydroxy-3-methylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
    1.6820   -1.9476   -5.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631   -2.1610   -5.1628 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.8701    0.3272   -2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.4229   -1.3865   -0.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458    0.9007   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908    0.7231    1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5108    2.0503    2.0796 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3323    0.7571    2.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9292    2.4502    6.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4927    1.6927    3.6231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0642    2.1417   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    3.2643   -0.4845 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1479    0.1049    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331    3.3678    3.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154    4.1187    4.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8042    3.6708    6.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1637    1.9537    6.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0234    0.8372    4.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3163    2.5691   -3.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    3.7492   -2.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519   -3.5776   -2.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
 26  7  1  0
 13 11  1  0
 21 22  1  0
 14 15  1  0
 11 10  2  0
 20 19  1  0
  8  9  2  0
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 24 25  2  0
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 23 18  1  0
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  4  5  1  1
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  4 28  1  0
 23 13  1  0
 28 30  1  0
 18 17  1  0
 28 29  2  0
 17 16  2  0
 26 27  1  0
 16 14  1  0
 18 50  1  6
 14 13  1  0
 23 59  1  1
  7 41  1  6
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 20 53  1  0
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  2 34  1  6
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 30 63  1  0
 27 60  1  0
 27 61  1  0
 27 62  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       1.682  -1.948  -5.246  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.163  -2.161  -5.163  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.134  -3.619  -5.553  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.422  -1.776  -3.765  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.111  -2.703  -2.803  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.072  -0.307  -3.395  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.870   0.327  -2.245  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.423  -0.204  -0.899  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.423  -1.387  -0.572  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.046   0.901  -0.037  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.491   0.723   1.220  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.554  -0.541   1.801  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.961   1.843   2.146  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.511   2.050   2.080  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.332   0.757   2.172  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.016   2.998   3.145  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.285   3.407   4.191  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.863   2.973   4.418  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.552   2.769   5.907  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.929   2.450   6.113  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.388   1.270   5.263  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.018   1.435   3.787  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.493   1.693   3.623  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.064   2.142  -0.833  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.244   3.264  -0.485  0.00  0.00           O+0
HETATM   26  N   UNK     0      -0.588   1.759  -2.063  0.00  0.00           N+0
HETATM   27  C   UNK     0      -0.942   2.729  -3.081  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.953  -1.951  -3.815  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.729  -1.162  -4.330  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.350  -3.085  -3.188  0.00  0.00           O+0
HETATM   31  H   UNK     0       2.066  -2.266  -6.222  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.211  -2.519  -4.476  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.945  -0.892  -5.132  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.304  -1.521  -5.924  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.302  -4.325  -4.839  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.281  -3.845  -6.541  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.210  -3.807  -5.609  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.036  -2.365  -1.893  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.222   0.309  -4.290  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.995  -0.248  -3.141  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.954   0.222  -2.334  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.217  -1.217   1.176  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.501   2.779   1.804  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.737   2.510   1.107  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.106   0.196   3.085  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.407   0.974   2.175  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.148   0.105   1.312  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.033   3.368   3.035  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.715   4.119   4.892  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.235   3.803   4.063  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.804   3.671   6.478  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.164   1.954   6.315  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.117   2.237   7.172  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.527   3.333   5.856  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.931   0.349   5.647  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.473   1.148   5.358  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.588   2.267   3.355  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.325   0.530   3.255  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.023   0.837   4.067  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.994   2.596  -3.344  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.316   2.569  -3.962  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.788   3.749  -2.719  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.552  -3.578  -2.882  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    4    1    3   34                                             
CONECT    3    2   35   36   37                                             
CONECT    4    6    2    5   28                                             
CONECT    5    4   38                                                       
CONECT    6    7    4   39   40                                             
CONECT    7   26    6    8   41                                             
CONECT    8    9    7   10                                                  
CONECT    9    8                                                            
CONECT   10   11    8   24                                                  
CONECT   11   13   10   12                                                  
CONECT   12   11   42                                                       
CONECT   13   11   23   14   43                                             
CONECT   14   15   16   13   44                                             
CONECT   15   14   45   46   47                                             
CONECT   16   17   14   48                                                  
CONECT   17   18   16   49                                                  
CONECT   18   19   23   17   50                                             
CONECT   19   20   18   51   52                                             
CONECT   20   19   21   53   54                                             
CONECT   21   22   20   55   56                                             
CONECT   22   21   23   57   58                                             
CONECT   23   22   18   13   59                                             
CONECT   24   25   10   26                                                  
CONECT   25   24                                                            
CONECT   26    7   24   27                                                  
CONECT   27   26   60   61   62                                             
CONECT   28    4   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28   63                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   27                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   30                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

RDKit          3D

63 65  0  0  0  0  0  0  0  0999 V2000
    1.6820   -1.9476   -5.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631   -2.1610   -5.1628 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.4227   -0.2041   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4229   -1.3865   -0.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458    0.9007   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9607    1.8426    2.1457 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5108    2.0503    2.0796 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3323    0.7571    2.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159    2.9975    3.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845    3.4067    4.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    2.9725    4.4180 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5515    2.7687    5.9073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9292    2.4502    6.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880    1.2696    5.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    1.4353    3.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    1.6927    3.6231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0642    2.1417   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    3.2643   -0.4845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877    1.7590   -2.0630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416    2.7290   -3.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -1.9512   -3.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293   -1.1620   -4.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0656   -2.2657   -6.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2107   -2.5190   -4.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449   -0.8918   -5.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036   -1.5211   -5.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -4.3255   -4.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2809   -3.8451   -6.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2105   -3.8073   -5.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -2.3649   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215    0.3093   -4.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -0.2480   -3.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2167   -1.2169    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5011    2.7789    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7371    2.5098    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064    0.1957    3.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073    0.9737    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479    0.1049    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331    3.3678    3.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154    4.1187    4.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    3.8028    4.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    3.6708    6.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1637    1.9537    6.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1170    2.2374    7.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273    3.3332    5.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310    0.3492    5.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5883    2.2669    3.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252    0.5295    3.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0234    0.8372    4.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9944    2.5962   -3.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    2.5691   -3.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    3.7492   -2.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519   -3.5776   -2.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
 26  7  1  0
 13 11  1  0
 21 22  1  0
 14 15  1  0
 11 10  2  0
 20 19  1  0
  8  9  2  0
 19 18  1  0
 24 25  2  0
 23 22  1  0
 11 12  1  0
 23 18  1  0
  7  6  1  0
  7  8  1  0
  6  4  1  0
  8 10  1  0
  4  2  1  0
 21 20  1  0
  2  1  1  0
 10 24  1  0
  2  3  1  0
  4  5  1  1
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  4 28  1  0
 23 13  1  0
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 17 16  2  0
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 16 14  1  0
 18 50  1  6
 14 13  1  0
 23 59  1  1
  7 41  1  6
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  5 38  1  0
 30 63  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S)-2-Hydroxy-2-[[(2S)-1-methyl-4-[[(1R)-2a-methyl-1,2,4abeta,5,6,7,8,8aalpha-octahydronaphthalene-1a-yl](hydroxy)methylene]-3,5-dioxopyrrolidine-2b-yl]methyl]-3-methylbutanoate	Generator
(2S)-2-Hydroxy-2-[[(2S)-1-methyl-4-[[(1R)-2a-methyl-1,2,4abeta,5,6,7,8,8aalpha-octahydronaphthalene-1a-yl](hydroxy)methylene]-3,5-dioxopyrrolidine-2b-yl]methyl]-3-methylbutanoic acid	Generator
(2S)-2-Hydroxy-2-[[(2S)-1-methyl-4-[[(1R)-2alpha-methyl-1,2,4abeta,5,6,7,8,8aalpha-octahydronaphthalene-1alpha-yl](hydroxy)methylene]-3,5-dioxopyrrolidine-2beta-yl]methyl]-3-methylbutanoate	Generator
(2S)-2-Hydroxy-2-[[(2S)-1-methyl-4-[[(1R)-2α-methyl-1,2,4abeta,5,6,7,8,8aalpha-octahydronaphthalene-1α-yl](hydroxy)methylene]-3,5-dioxopyrrolidine-2β-yl]methyl]-3-methylbutanoate	Generator
(2S)-2-Hydroxy-2-[[(2S)-1-methyl-4-[[(1R)-2α-methyl-1,2,4abeta,5,6,7,8,8aalpha-octahydronaphthalene-1α-yl](hydroxy)methylene]-3,5-dioxopyrrolidine-2β-yl]methyl]-3-methylbutanoic acid	Generator

Chemical Formula

C₂₃H₃₃NO₆

Average Mass

419.5180 Da

Monoisotopic Mass

419.23079 Da

IUPAC Name

(2S)-2-{[(2S,4E)-4-{[(1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl}-2-hydroxy-3-methylbutanoic acid

Traditional Name

(2S)-2-{[(2S,4E)-4-{[(1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl}-2-hydroxy-3-methylbutanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@](O[H])(C([H])([H])[C@]1([H])N(C(=O)\C(=C(\O[H])[C@]2([H])[C@@]([H])(C([H])=C([H])[C@]3([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]23[H])C([H])([H])[H])C1=O)C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H33NO6/c1-12(2)23(30,22(28)29)11-16-19(25)18(21(27)24(16)4)20(26)17-13(3)9-10-14-7-5-6-8-15(14)17/h9-10,12-17,26,30H,5-8,11H2,1-4H3,(H,28,29)/b20-18+/t13-,14+,15-,16+,17-,23+/m1/s1

InChI Key

DIFKWHRMEGFLSD-DBEUHZBBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Verticillium sp. f21794	JEOL database	Izumikawa, M., et al, J. Nat. Prod. 73, 628 (2010)

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

Methyl-branched fatty acid
Branched fatty acid
Hydroxy fatty acid
Heterocyclic fatty acid
Pyrrolidone
2-pyrrolidone
3-pyrrolidone
N-alkylpyrrolidine
Alpha-hydroxy acid
Hydroxy acid
Tertiary carboxylic acid amide
Tertiary alcohol
Vinylogous acid
Pyrrolidine
Lactam
Cyclic ketone
Ketone
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Enol
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
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	2.29	ALOGPS
logP	2.55	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-0.77	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	115.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.37 m³·mol⁻¹	ChemAxon
Polarizability	45.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24672107

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54726846

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Izumikawa, M., et al. (2010). Izumikawa, M., et al, J. Nat. Prod. 73, 628 (2010). J. Nat. Prod..

Showing NP-Card for JBIR 22 (NP0039385)

MOL for NP0039385 (JBIR 22)

3D MOL for NP0039385 (JBIR 22)

3D SDF for NP0039385 (JBIR 22)

3D-SDF for NP0039385 (JBIR 22)

PDB for NP0039385 (JBIR 22)

3D PDB for NP0039385 (JBIR 22)

SMILES for NP0039385 (JBIR 22)

INCHI for NP0039385 (JBIR 22)

Structure for NP0039385 (JBIR 22)

3D Structure for NP0039385 (JBIR 22)