NP-MRD: Showing NP-Card for haterumaimide N (NP0027454)

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Record Information

Version

2.0

Created at

2021-06-19 19:36:28 UTC

Updated at

2021-06-29 23:53:35 UTC

NP-MRD ID

NP0027454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

haterumaimide N

Provided By

JEOL Database JEOL Logo

Description

haterumaimide N is found in Pleurobranchus albiguttatus and P. forskalii. haterumaimide N was first documented in 2004 (Fu, X., et al.). Based on a literature review very few articles have been published on 3beta-hydroxylissoclimide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121363D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192121363D          

 57 59  0  0  0  0            999 V2000
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   -3.3356    1.8580    0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200    2.9172    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183    3.1091   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360    1.7806   -2.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436    0.1563   -2.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7854    0.5569   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343    1.4151   -2.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081    3.7027   -2.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409    3.0766   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    1.2793    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483    0.3390   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    2.1512    1.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1587    0.7207    2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5631    1.0722    2.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6253   -1.7202   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -0.7455    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.5967    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8522   -3.2815    2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -2.1906    3.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0488   -3.2801   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -2.5171   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4855   -1.7496    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -5.7376    0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0  0  0  0
 21 26  1  0  0  0  0
 10  7  1  0  0  0  0
  7  6  1  0  0  0  0
 15 14  1  0  0  0  0
 15 17  1  0  0  0  0
 26 25  1  0  0  0  0
 25 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
  6  5  1  0  0  0  0
 26 27  2  0  0  0  0
  5  3  1  0  0  0  0
 23 24  2  0  0  0  0
  3  2  1  0  0  0  0
 21 54  1  6  0  0  0
  2 17  1  0  0  0  0
  7  8  1  1  0  0  0
 15  6  1  0  0  0  0
 19 20  1  0  0  0  0
  2  1  2  3  0  0  0
 15 16  1  1  0  0  0
  7  9  1  0  0  0  0
 17 18  1  0  0  0  0
 10 11  1  0  0  0  0
 12 10  1  0  0  0  0
 12 13  1  0  0  0  0
 18 19  1  0  0  0  0
  6 34  1  6  0  0  0
 12 14  1  0  0  0  0
  3  4  1  0  0  0  0
 12 43  1  1  0  0  0
 10 41  1  6  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  3 30  1  6  0  0  0
 17 49  1  6  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 19 52  1  1  0  0  0
 25 57  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
 20 53  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
 16 48  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 11 42  1  0  0  0  0
  4 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C([H])([H])[C@@]1([H])C(=C([H])[H])[C@@]([H])(O[H])C([H])([H])[C@@]2([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(Cl)C([H])([H])[C@]12C([H])([H])[H])[C@]1([H])C(=O)N([H])C(=O)C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30ClNO5/c1-9-11(6-14(24)10-5-16(25)22-18(10)27)20(4)8-12(21)17(26)19(2,3)15(20)7-13(9)23/h10-15,17,23-24,26H,1,5-8H2,2-4H3,(H,22,25,27)/t10-,11+,12-,13+,14+,15+,17+,20-/m1/s1

> <INCHI_KEY>
UACZEBODXTXUMI-VVHTYQJQSA-N

> <FORMULA>
C20H30ClNO5

> <MOLECULAR_WEIGHT>
399.91

> <EXACT_MASS>
399.1812508

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.597018117700514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-[(1S)-2-[(1R,3S,4aR,6R,7R,8aS)-7-chloro-3,6-dihydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-1-hydroxyethyl]pyrrolidine-2,5-dione

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
0.4534111906666667

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.708826800882257

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.983783567848992

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2731295347887226

> <JCHEM_POLAR_SURFACE_AREA>
106.85999999999999

> <JCHEM_REFRACTIVITY>
100.48919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(1S)-2-[(1R,3S,4aR,6R,7R,8aS)-7-chloro-3,6-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]pyrrolidine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -0.6041   -2.2546    2.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6400   -1.8994    1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -2.0949    0.7117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9095   -2.7685    1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3939   -0.7406    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984    0.0845   -0.4855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8323    1.3640   -1.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5831    2.3581   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    0.9368   -2.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446    2.0554   -1.9670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0852    3.2923   -2.5388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664    2.3032   -1.0595 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9098    2.9990   -2.0426 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0633    1.0203   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0207    0.2788    0.4337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2988    1.0949    1.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -1.1784    0.8392 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8797   -1.2136    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -2.6152    1.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7039   -2.4645    2.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925   -3.2699    0.3442 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1339   -2.6828   -0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748   -3.7542   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3434   -3.6568   -0.5293 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -4.8718    0.3040 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -4.7064    0.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -5.5824    0.9926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -2.7155    3.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -2.0643    3.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -2.7130   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -3.6647    1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8201   -0.1874    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2385   -0.9385   -0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507   -0.5683   -1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3356    1.8580    0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200    2.9172    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183    3.1091   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360    1.7806   -2.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436    0.1563   -2.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7854    0.5569   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343    1.4151   -2.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081    3.7027   -2.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409    3.0766   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    1.2793    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483    0.3390   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    2.1512    1.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1587    0.7207    2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5631    1.0722    2.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6253   -1.7202   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -0.7455    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.5967    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8522   -3.2815    2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -2.1906    3.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0488   -3.2801   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -2.5171   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4855   -1.7496    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -5.7376    0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0
 21 26  1  0
 10  7  1  0
  7  6  1  0
 15 14  1  0
 15 17  1  0
 26 25  1  0
 25 23  1  0
 23 22  1  0
 22 21  1  0
  6  5  1  0
 26 27  2  0
  5  3  1  0
 23 24  2  0
  3  2  1  0
 21 54  1  6
  2 17  1  0
  7  8  1  1
 15  6  1  0
 19 20  1  0
  2  1  2  3
 15 16  1  1
  7  9  1  0
 17 18  1  0
 10 11  1  0
 12 10  1  0
 12 13  1  0
 18 19  1  0
  6 34  1  6
 12 14  1  0
  3  4  1  0
 12 43  1  1
 10 41  1  6
 14 44  1  0
 14 45  1  0
  5 32  1  0
  5 33  1  0
  3 30  1  6
 17 49  1  6
  1 28  1  0
  1 29  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  1
 25 57  1  0
 22 55  1  0
 22 56  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 20 53  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 11 42  1  0
  4 31  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.604  -2.255   2.885  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.640  -1.899   1.586  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.864  -2.095   0.712  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.910  -2.769   1.398  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.394  -0.741   0.231  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.298   0.085  -0.486  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.832   1.364  -1.231  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.583   2.358  -0.320  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.857   0.937  -2.322  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.645   2.055  -1.967  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.085   3.292  -2.539  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.566   2.303  -1.060  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       1.910   2.999  -2.043  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       1.063   1.020  -0.393  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.021   0.279   0.434  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.299   1.095   1.721  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.490  -1.178   0.839  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.880  -1.214   1.533  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.513  -2.615   1.680  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.704  -2.465   2.464  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.893  -3.270   0.344  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.134  -2.683  -0.333  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.175  -3.754  -0.193  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.343  -3.657  -0.529  0.00  0.00           O+0
HETATM   25  N   UNK     0       4.593  -4.872   0.304  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.280  -4.706   0.593  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.529  -5.582   0.993  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.458  -2.716   3.374  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.246  -2.064   3.529  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.596  -2.713  -0.154  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.584  -3.665   1.588  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.820  -0.187   1.076  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.239  -0.939  -0.437  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.951  -0.568  -1.305  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.336   1.858   0.297  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.920   2.917   0.339  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.118   3.109  -0.914  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.136   1.781  -2.963  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.444   0.156  -2.971  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.785   0.557  -1.885  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.334   1.415  -2.805  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.308   3.703  -2.963  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.341   3.077  -0.320  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.914   1.279   0.249  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.448   0.339  -1.165  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.477   2.151   1.524  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.159   0.721   2.283  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.563   1.072   2.396  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.625  -1.720  -0.106  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.825  -0.746   2.523  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.594  -0.597   0.979  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.852  -3.281   2.242  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.436  -2.191   3.360  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.049  -3.280  -0.352  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.948  -2.517  -1.400  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.486  -1.750   0.114  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.088  -5.738   0.440  0.00  0.00           H+0
CONECT    1    2   28   29                                                  
CONECT    2    3   17    1                                                  
CONECT    3    5    2    4   30                                             
CONECT    4    3   31                                                       
CONECT    5    6    3   32   33                                             
CONECT    6    7    5   15   34                                             
CONECT    7   10    6    8    9                                             
CONECT    8    7   35   36   37                                             
CONECT    9    7   38   39   40                                             
CONECT   10    7   11   12   41                                             
CONECT   11   10   42                                                       
CONECT   12   10   13   14   43                                             
CONECT   13   12                                                            
CONECT   14   15   12   44   45                                             
CONECT   15   14   17    6   16                                             
CONECT   16   15   46   47   48                                             
CONECT   17   15    2   18   49                                             
CONECT   18   17   19   50   51                                             
CONECT   19   21   20   18   52                                             
CONECT   20   19   53                                                       
CONECT   21   19   26   22   54                                             
CONECT   22   23   21   55   56                                             
CONECT   23   25   22   24                                                  
CONECT   24   23                                                            
CONECT   25   26   23   57                                                  
CONECT   26   21   25   27                                                  
CONECT   27   26                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   25                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
   -0.6041   -2.2546    2.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6400   -1.8994    1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -2.0949    0.7117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9095   -2.7685    1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3939   -0.7406    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984    0.0845   -0.4855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8323    1.3640   -1.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5831    2.3581   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    0.9368   -2.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446    2.0554   -1.9670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0852    3.2923   -2.5388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664    2.3032   -1.0595 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9098    2.9990   -2.0426 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0633    1.0203   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0207    0.2788    0.4337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2988    1.0949    1.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -1.1784    0.8392 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8797   -1.2136    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -2.6152    1.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7039   -2.4645    2.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925   -3.2699    0.3442 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1339   -2.6828   -0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748   -3.7542   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3434   -3.6568   -0.5293 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -4.8718    0.3040 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -4.7064    0.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -5.5824    0.9926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -2.7155    3.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -2.0643    3.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -2.7130   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -3.6647    1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8201   -0.1874    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2385   -0.9385   -0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507   -0.5683   -1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3356    1.8580    0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200    2.9172    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183    3.1091   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360    1.7806   -2.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436    0.1563   -2.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7854    0.5569   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343    1.4151   -2.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081    3.7027   -2.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3409    3.0766   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    1.2793    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483    0.3390   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    2.1512    1.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1587    0.7207    2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5631    1.0722    2.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6253   -1.7202   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -0.7455    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.5967    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8522   -3.2815    2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -2.1906    3.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0488   -3.2801   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -2.5171   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4855   -1.7496    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -5.7376    0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0
 21 26  1  0
 10  7  1  0
  7  6  1  0
 15 14  1  0
 15 17  1  0
 26 25  1  0
 25 23  1  0
 23 22  1  0
 22 21  1  0
  6  5  1  0
 26 27  2  0
  5  3  1  0
 23 24  2  0
  3  2  1  0
 21 54  1  6
  2 17  1  0
  7  8  1  1
 15  6  1  0
 19 20  1  0
  2  1  2  3
 15 16  1  1
  7  9  1  0
 17 18  1  0
 10 11  1  0
 12 10  1  0
 12 13  1  0
 18 19  1  0
  6 34  1  6
 12 14  1  0
  3  4  1  0
 12 43  1  1
 10 41  1  6
 14 44  1  0
 14 45  1  0
  5 32  1  0
  5 33  1  0
  3 30  1  6
 17 49  1  6
  1 28  1  0
  1 29  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  1
 25 57  1  0
 22 55  1  0
 22 56  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 20 53  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 11 42  1  0
  4 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
3b-Hydroxylissoclimide	Generator
3Β-hydroxylissoclimide	Generator

Chemical Formula

C₂₀H₃₀ClNO₅

Average Mass

399.9100 Da

Monoisotopic Mass

399.18125 Da

IUPAC Name

(3R)-3-[(1S)-2-[(1R,3S,4aR,6R,7R,8aS)-7-chloro-3,6-dihydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-1-hydroxyethyl]pyrrolidine-2,5-dione

Traditional Name

(3R)-3-[(1S)-2-[(1R,3S,4aR,6R,7R,8aS)-7-chloro-3,6-dihydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]pyrrolidine-2,5-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]([H])(C([H])([H])[C@@]1([H])C(=C([H])[H])[C@@]([H])(O[H])C([H])([H])[C@@]2([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(Cl)C([H])([H])[C@]12C([H])([H])[H])[C@]1([H])C(=O)N([H])C(=O)C1([H])[H]

InChI Identifier

InChI=1S/C20H30ClNO5/c1-9-11(6-14(24)10-5-16(25)22-18(10)27)20(4)8-12(21)17(26)19(2,3)15(20)7-13(9)23/h10-15,17,23-24,26H,1,5-8H2,2-4H3,(H,22,25,27)/t10-,11+,12-,13+,14+,15+,17+,20-/m1/s1

InChI Key

UACZEBODXTXUMI-VVHTYQJQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₂Cl₂, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₂Cl₂, 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
Pleurobranchus albiguttatus	JEOL database	Fu, X., et al, J. Nat. Prod. 67, 1415 (2004)
Pleurobranchus forskalii	JEOL database	Fu, X., et al, J. Nat. Prod. 67, 1415 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Pyrrolidones

Direct Parent

Pyrrolidine-2-ones

Alternative Parents

Substituents

2-pyrrolidone
Carboxylic acid imide
Cyclic alcohol
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Chlorohydrin
Secondary alcohol
Halohydrin
Lactam
Carboxylic acid derivative
Azacycle
Organohalogen compound
Alkyl halide
Organooxygen compound
Organic nitrogen compound
Alkyl chloride
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organochloride
Organonitrogen compound
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	1.55	ALOGPS
logP	0.45	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.49 m³·mol⁻¹	ChemAxon
Polarizability	41.6 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

9581806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11406911

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fu, X., et al. (2004). Fu, X., et al, J. Nat. Prod. 67, 1415 (2004). J. Nat. Prod..

Showing NP-Card for haterumaimide N (NP0027454)

MOL for NP0027454 (haterumaimide N)

3D MOL for NP0027454 (haterumaimide N)

3D SDF for NP0027454 (haterumaimide N)

3D-SDF for NP0027454 (haterumaimide N)

PDB for NP0027454 (haterumaimide N)

3D PDB for NP0027454 (haterumaimide N)

SMILES for NP0027454 (haterumaimide N)

INCHI for NP0027454 (haterumaimide N)

Structure for NP0027454 (haterumaimide N)

3D Structure for NP0027454 (haterumaimide N)