NP-MRD: Showing NP-Card for Cinnabaramide E (NP0006841)

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Record Information

Version

1.0

Created at

2020-12-09 03:45:47 UTC

Updated at

2021-07-15 16:55:56 UTC

NP-MRD ID

NP0006841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinnabaramide E

Provided By

NPAtlas

Description

Cinnabaramide E belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Cinnabaramide E is found in Streptomyces sp. It was first documented in 2007 (PMID: 17249727). Based on a literature review very few articles have been published on cinnabaramide E (PMID: 27490092).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118353D          

 56 57  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306242118353D          

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    1.5077    1.0139   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5306    0.0199   -2.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -1.9965   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839    0.3512    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302    3.5387   -0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -1.0331    1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433    0.4026    2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -0.7984   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    2.2373    0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154    1.8994   -0.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604   -0.9436   -0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8060   -0.1540    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0613   -0.6654    2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351   -1.9590    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1049    0.5065    2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4235   -1.1921    2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917   -1.4474   -2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.4149   -1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -2.2498   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915   -0.2389   -3.0583 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
 23  7  1  0  0  0  0
 22 17  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
  2 29  1  0  0  0  0
  2 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
  7 39  1  6  0  0  0
 10 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  1  0  0  0
 16 43  1  0  0  0  0
 17 44  1  6  0  0  0
 18 45  1  0  0  0  0
 19 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 25 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006841

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H31NO5/c1-3-4-5-9-12-14-16(22)20-19(17(23)24,18(14,2)25)15(21)13-10-7-6-8-11-13/h7,10,13-15,21,25H,3-6,8-9,11-12H2,1-2H3,(H,20,22)(H,23,24)/t13-,14+,15+,18+,19+/m1/s1

> <INCHI_KEY>
ADDRECXFKLYOGC-MUAMBBPCSA-N

> <FORMULA>
C19H31NO5

> <MOLECULAR_WEIGHT>
353.459

> <EXACT_MASS>
353.220223102

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.470185741398616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4R)-2-[(S)-[(1S)-cyclohex-2-en-1-yl](hydroxy)methyl]-4-hexyl-3-hydroxy-3-methyl-5-oxopyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.435725023333334

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.241693875062765

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8940876065317247

> <JCHEM_PKA_STRONGEST_BASIC>
-1.774434058135196

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
94.3018

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R)-2-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-4-hexyl-3-hydroxy-3-methyl-5-oxopyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    6.2689    1.1728    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924    1.2578    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9539    1.2220    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517   -0.0682   -0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233   -0.0891   -1.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736   -0.0117   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -1.0066   -1.1815 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2505   -1.1567    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9094   -2.0554    0.8874 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -0.0776    0.8851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6145    0.3123    0.0646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4420    1.7659   -0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    2.3869    0.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    2.5439   -1.0559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391    0.0127    0.9503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5648    0.8248    2.1061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1336    0.0477    0.5915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7936    1.2634    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1046    1.0917   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7070   -0.2826    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2905   -0.8602    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584   -0.3820    1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -0.5025   -1.1490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3218   -1.6715   -1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    0.3554   -2.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5899    0.1803    0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7844    1.3898    2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6252    1.9084    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433    0.4457    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5700    2.2078    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9022    1.3486    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787    2.0662   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2541    0.0065   -0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352   -0.8953    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -0.9720   -2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    0.7799   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077    1.0139   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5306    0.0199   -2.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -1.9965   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839    0.3512    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302    3.5387   -0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -1.0331    1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433    0.4026    2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -0.7984   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    2.2373    0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154    1.8994   -0.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604   -0.9436   -0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8060   -0.1540    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0613   -0.6654    2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351   -1.9590    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1049    0.5065    2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4235   -1.1921    2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917   -1.4474   -2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.4149   -1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -2.2498   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915   -0.2389   -3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  6
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  1  0
 23 25  1  6
 23  7  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  6
 10 40  1  0
 14 41  1  0
 15 42  1  1
 16 43  1  0
 17 44  1  6
 18 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.269   1.173   1.093  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.792   1.258   1.387  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.954   1.222   0.145  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.152  -0.068  -0.657  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.323  -0.089  -1.865  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.874  -0.012  -1.832  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.025  -1.007  -1.182  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.250  -1.157   0.258  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.909  -2.055   0.887  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.574  -0.078   0.885  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.615   0.312   0.065  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.442   1.766  -0.141  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.405   2.387   0.586  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.105   2.544  -1.056  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.739   0.013   0.950  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.565   0.825   2.106  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.134   0.048   0.592  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.794   1.263   0.139  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.105   1.092  -0.157  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.707  -0.283   0.013  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.290  -0.860   1.355  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.958  -0.382   1.835  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.434  -0.502  -1.149  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.322  -1.672  -1.353  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.596   0.355  -2.261  0.00  0.00           O+0
HETATM   26  H   UNK     0       6.590   0.180   0.768  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.784   1.390   2.063  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.625   1.908   0.374  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.543   0.446   2.091  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.570   2.208   1.918  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.902   1.349   0.444  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.179   2.066  -0.539  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.254   0.007  -0.962  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.135  -0.895   0.032  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.671  -0.972  -2.499  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.684   0.780  -2.513  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.508   1.014  -1.486  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.531   0.020  -2.929  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.998  -1.996  -1.712  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.884   0.351   1.784  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.230   3.539  -0.937  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.532  -1.033   1.382  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.043   0.403   2.801  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.441  -0.798  -0.130  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.415   2.237   0.028  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.715   1.899  -0.507  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.460  -0.944  -0.836  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.806  -0.154   0.046  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.061  -0.665   2.136  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.235  -1.959   1.230  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.105   0.506   2.474  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.424  -1.192   2.381  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.192  -1.447  -2.038  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.740  -2.415  -1.987  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.590  -2.250  -0.465  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.592  -0.239  -3.058  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3   29   30                                             
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   33   34                                             
CONECT    5    4    6   35   36                                             
CONECT    6    5    7   37   38                                             
CONECT    7    6    8   23   39                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   40                                                  
CONECT   11   10   12   15   23                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   41                                                       
CONECT   15   11   16   17   42                                             
CONECT   16   15   43                                                       
CONECT   17   15   18   22   44                                             
CONECT   18   17   19   45                                                  
CONECT   19   18   20   46                                                  
CONECT   20   19   21   47   48                                             
CONECT   21   20   22   49   50                                             
CONECT   22   21   17   51   52                                             
CONECT   23   11   24   25    7                                             
CONECT   24   23   53   54   55                                             
CONECT   25   23   56                                                       
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    6                                                            
CONECT   39    7                                                            
CONECT   40   10                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  114    0
END

RDKit          3D

56 57  0  0  0  0  0  0  0  0999 V2000
    6.2689    1.1728    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924    1.2578    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9539    1.2220    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517   -0.0682   -0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233   -0.0891   -1.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736   -0.0117   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -1.0066   -1.1815 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2505   -1.1567    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9094   -2.0554    0.8874 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -0.0776    0.8851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6145    0.3123    0.0646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4420    1.7659   -0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    2.3869    0.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    2.5439   -1.0559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391    0.0127    0.9503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5648    0.8248    2.1061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1336    0.0477    0.5915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7936    1.2634    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1046    1.0917   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7070   -0.2826    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2905   -0.8602    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584   -0.3820    1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -0.5025   -1.1490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3218   -1.6715   -1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    0.3554   -2.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5899    0.1803    0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7844    1.3898    2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6252    1.9084    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433    0.4457    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5700    2.2078    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9022    1.3486    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787    2.0662   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2541    0.0065   -0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352   -0.8953    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -0.9720   -2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    0.7799   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077    1.0139   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5306    0.0199   -2.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -1.9965   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839    0.3512    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302    3.5387   -0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -1.0331    1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433    0.4026    2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -0.7984   -0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    2.2373    0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154    1.8994   -0.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4604   -0.9436   -0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8060   -0.1540    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0613   -0.6654    2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351   -1.9590    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1049    0.5065    2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4235   -1.1921    2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917   -1.4474   -2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.4149   -1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896   -2.2498   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915   -0.2389   -3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  6
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  1  0
 23 25  1  6
 23  7  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  6
 10 40  1  0
 14 41  1  0
 15 42  1  1
 16 43  1  0
 17 44  1  6
 18 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,3S,4R)-2-[(S)-[(1S)-Cyclohex-2-en-1-yl](hydroxy)methyl]-4-hexyl-3,5-dihydroxy-3-methyl-3,4-dihydro-2H-pyrrole-2-carboxylate	Generator

Chemical Formula

C₁₉H₃₁NO₅

Average Mass

353.4590 Da

Monoisotopic Mass

353.22022 Da

IUPAC Name

(2R,3S,4R)-2-[(S)-[(1S)-cyclohex-2-en-1-yl](hydroxy)methyl]-4-hexyl-3-hydroxy-3-methyl-5-oxopyrrolidine-2-carboxylic acid

Traditional Name

(2R,3S,4R)-2-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-4-hexyl-3-hydroxy-3-methyl-5-oxopyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCC[C@H]1C(=O)N[C@@]([C@@H](O)[C@H]2CCCC=C2)(C(O)=O)[C@@]1(C)O

InChI Identifier

InChI=1S/C19H31NO5/c1-3-4-5-9-12-14-16(22)20-19(17(23)24,18(14,2)25)15(21)13-10-7-6-8-11-13/h7,10,13-15,21,25H,3-6,8-9,11-12H2,1-2H3,(H,20,22)(H,23,24)/t13-,14+,15+,18+,19+/m1/s1

InChI Key

ADDRECXFKLYOGC-MUAMBBPCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces sp.	NPAtlas	17249727

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Pyrrolidone
2-pyrrolidone
Tertiary alcohol
Pyrrolidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Alcohol
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.28	ALOGPS
logP	2.44	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	94.3 m³·mol⁻¹	ChemAxon
Polarizability	38.47 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

NPAtlas ID

NPA017304

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038769

Chemspider ID

17214467

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16109814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stadler M, Bitzer J, Mayer-Bartschmid A, Muller H, Benet-Buchholz J, Gantner F, Tichy HV, Reinemer P, Bacon KB: Cinnabaramides A-G: analogues of lactacystin and salinosporamide from a terrestrial streptomycete. J Nat Prod. 2007 Feb;70(2):246-52. doi: 10.1021/np060162u. Epub 2007 Jan 24. [PubMed:17249727 ]
Chen S, Ibrahim AA, Peraino NJ, Nalla D, Mondal M, Van Raaphorst M, Kerrigan NJ: Catalytic Asymmetric Synthesis of Ketene Heterodimer beta-Lactones: Scope and Limitations. J Org Chem. 2016 Sep 2;81(17):7824-37. doi: 10.1021/acs.joc.6b01481. Epub 2016 Aug 12. [PubMed:27490092 ]

Showing NP-Card for Cinnabaramide E (NP0006841)

MOL for NP0006841 (Cinnabaramide E)

3D MOL for NP0006841 (Cinnabaramide E)

3D SDF for NP0006841 (Cinnabaramide E)

3D-SDF for NP0006841 (Cinnabaramide E)

PDB for NP0006841 (Cinnabaramide E)

3D PDB for NP0006841 (Cinnabaramide E)

SMILES for NP0006841 (Cinnabaramide E)

INCHI for NP0006841 (Cinnabaramide E)

Structure for NP0006841 (Cinnabaramide E)

3D Structure for NP0006841 (Cinnabaramide E)