NP-MRD: Showing NP-Card for calafianin (NP0029182)

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Record Information

Version

2.0

Created at

2021-06-19 20:52:44 UTC

Updated at

2021-06-29 23:56:23 UTC

NP-MRD ID

NP0029182

Secondary Accession Numbers

None

Natural Product Identification

Common Name

calafianin

Provided By

JEOL Database JEOL Logo

Description

calafianin is found in Aplysina gerardogreeni. calafianin was first documented in 2000 (Encarnacion, R. D., et al.). Based on a literature review very few articles have been published on (+)-epi-Calafianin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122523D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192122523D          

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   -2.2725   -1.0428    0.2463 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4629   -1.3391    1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925    1.5820    2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975    0.5088    3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    1.0156    2.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -0.7034    2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708   -0.0101    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -0.7010    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    1.4187   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674    2.3360    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    0.6452   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590    3.3206   -4.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5028    3.8383    0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    2.6513    0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549    4.2699   -0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    4.1522   -2.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1144   -1.4096   -2.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7429   -2.9715   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524   -3.0972    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678   -1.1721    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -0.0777   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 25 24  2  0  0  0  0
 29 30  1  0  0  0  0
 14 13  1  6  0  0  0
 24  2  1  0  0  0  0
 24 36  1  0  0  0  0
  2  3  1  0  0  0  0
 27 36  1  0  0  0  0
  3  4  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  2  0  0  0  0
 11 23  1  0  0  0  0
 14 23  1  0  0  0  0
 27 26  1  1  0  0  0
  4  5  1  0  0  0  0
 20 18  1  0  0  0  0
 22 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 18  1  0  0  0  0
 31 32  2  0  0  0  0
 11  9  1  0  0  0  0
 33 35  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 35 34  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 26 25  1  0  0  0  0
 18 19  2  0  0  0  0
 20 22  1  0  0  0  0
 22 21  1  0  0  0  0
 33 31  1  0  0  0  0
 35 27  1  0  0  0  0
 27 28  1  0  0  0  0
 33 53  1  1  0  0  0
 20 48  1  1  0  0  0
 28 29  2  0  0  0  0
 22 49  1  1  0  0  0
 35 54  1  1  0  0  0
  9 10  2  0  0  0  0
 29 31  1  0  0  0  0
 16 17  1  0  0  0  0
 33 34  1  0  0  0  0
 20 21  1  0  0  0  0
 36 55  1  0  0  0  0
 36 56  1  0  0  0  0
 28 52  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  0  0  0  0
  4 39  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 15 47  1  0  0  0  0
  8 46  1  0  0  0  0
  7 44  1  0  0  0  0
  7 45  1  0  0  0  0
  6 42  1  0  0  0  0
  6 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029182

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C(=O)C1=NO[C@]2(C([H])=C(Br)C(=O)[C@@]3([H])O[C@@]23[H])C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=O)C1=NO[C@]2(C([H])=C(Br)C(=O)[C@@]3([H])O[C@@]23[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20Br2N4O8/c23-9-5-21(17-15(33-17)13(9)29)7-11(27-35-21)19(31)25-3-1-2-4-26-20(32)12-8-22(36-28-12)6-10(24)14(30)16-18(22)34-16/h5-6,15-18H,1-4,7-8H2,(H,25,31)(H,26,32)/t15-,16-,17-,18-,21-,22-/m1/s1

> <INCHI_KEY>
OPMAEHVWCSXSKG-GARQETNWSA-N

> <FORMULA>
C22H20Br2N4O8

> <MOLECULAR_WEIGHT>
628.23

> <EXACT_MASS>
625.96479

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
50.90454227249876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6S)-4-bromo-N-(4-{[(1R,2S,6S)-4-bromo-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-en-4'-yl]formamido}butyl)-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-ene-4'-carboxamide

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.5801002126666668

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.494240091471198

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.957770040526086

> <JCHEM_PKA_STRONGEST_BASIC>
0.31227117271933513

> <JCHEM_POLAR_SURFACE_AREA>
160.58

> <JCHEM_REFRACTIVITY>
128.1056

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6S)-4-bromo-N-{4-[(1R,2S,6S)-4-bromo-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-en-4'-ylformamido]butyl}-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-ene-4'-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
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    2.0330    0.5639    2.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5122    0.2547    2.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9889    0.1723    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    1.4302   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1572    1.2800   -1.7233 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5285    3.4196   -3.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5763    4.1566   -1.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5991    4.8270   -1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5817    3.6041   -1.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8467   -1.1790    0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -2.3095    0.3187 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3677   -2.2164   -0.7226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1223   -1.7602   -2.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404   -1.7353   -3.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -1.0797   -4.8270 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4407   -2.2092   -2.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3556   -2.0379   -3.6852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7018   -2.9074   -1.6097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8865   -4.0774   -1.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6611   -2.9603   -0.5271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2725   -1.0428    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629   -1.3391    1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925    1.5820    2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975    0.5088    3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    1.0156    2.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -0.7034    2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708   -0.0101    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -0.7010    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    1.4187   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674    2.3360    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    0.6452   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590    3.3206   -4.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5028    3.8383    0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    2.6513    0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549    4.2699   -0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    4.1522   -2.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1144   -1.4096   -2.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7429   -2.9715   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524   -3.0972    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678   -1.1721    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -0.0777   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
 25 24  2  0
 29 30  1  0
 14 13  1  6
 24  2  1  0
 24 36  1  0
  2  3  1  0
 27 36  1  0
  3  4  1  0
 13 12  1  0
 12 11  2  0
 11 23  1  0
 14 23  1  0
 27 26  1  1
  4  5  1  0
 20 18  1  0
 22 14  1  0
 14 15  1  0
 15 16  2  0
 16 18  1  0
 31 32  2  0
 11  9  1  0
 33 35  1  0
  9  8  1  0
  8  7  1  0
 35 34  1  0
  7  6  1  0
  6  5  1  0
 26 25  1  0
 18 19  2  0
 20 22  1  0
 22 21  1  0
 33 31  1  0
 35 27  1  0
 27 28  1  0
 33 53  1  1
 20 48  1  1
 28 29  2  0
 22 49  1  1
 35 54  1  1
  9 10  2  0
 29 31  1  0
 16 17  1  0
 33 34  1  0
 20 21  1  0
 36 55  1  0
 36 56  1  0
 28 52  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
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 23 50  1  0
 23 51  1  0
 15 47  1  0
  8 46  1  0
  7 44  1  0
  7 45  1  0
  6 42  1  0
  6 43  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  O   UNK     0      -0.674   1.017   1.469  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.117  -0.057   1.299  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.165  -0.378   1.671  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.033   0.564   2.337  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.512   0.255   2.129  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.989   0.172   0.672  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.743   1.430  -0.159  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.398   1.480  -0.683  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.655   2.632  -0.746  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.994   3.742  -0.370  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.290   2.440  -1.360  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.157   1.280  -1.723  0.00  0.00           N+0
HETATM   13  O   UNK     0      -1.446   1.506  -2.265  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.870   2.849  -1.932  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.529   3.420  -3.164  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.736   4.009  -3.206  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -4.418   4.691  -4.809  0.00  0.00          Br+0
HETATM   18  C   UNK     0      -4.576   4.157  -1.976  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.599   4.827  -1.932  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.103   3.462  -0.757  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.988   2.033  -0.895  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.768   2.776  -0.723  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.582   3.604  -1.624  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.847  -1.179   0.603  0.00  0.00           C+0
HETATM   25  N   UNK     0      -0.283  -2.309   0.319  0.00  0.00           N+0
HETATM   26  O   UNK     0      -1.278  -3.088  -0.335  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.368  -2.216  -0.723  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.122  -1.760  -2.145  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.040  -1.735  -3.126  0.00  0.00           C+0
HETATM   30 Br   UNK     0      -2.620  -1.080  -4.827  0.00  0.00          Br+0
HETATM   31  C   UNK     0      -4.441  -2.209  -2.890  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.356  -2.038  -3.685  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.702  -2.907  -1.610  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.886  -4.077  -1.402  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.661  -2.960  -0.527  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.272  -1.043   0.246  0.00  0.00           C+0
HETATM   37  H   UNK     0       1.463  -1.339   1.518  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.793   1.582   2.015  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.798   0.509   3.406  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.103   1.016   2.654  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.745  -0.703   2.611  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.071  -0.010   0.698  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.541  -0.701   0.182  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.404   1.419  -1.033  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.967   2.336   0.414  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.985   0.645  -1.091  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.959   3.321  -4.087  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.503   3.838   0.178  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.252   2.651   0.219  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.655   4.270  -0.760  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.171   4.152  -2.478  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.114  -1.410  -2.361  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.743  -2.971  -1.317  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.952  -3.097   0.505  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.868  -1.172   1.156  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.504  -0.078  -0.203  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1   24    3                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5   38   39                                             
CONECT    5    4    6   40   41                                             
CONECT    6    7    5   42   43                                             
CONECT    7    8    6   44   45                                             
CONECT    8    9    7   46                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12   23    9                                                  
CONECT   12   13   11                                                       
CONECT   13   14   12                                                       
CONECT   14   13   23   22   15                                             
CONECT   15   14   16   47                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   20   16   19                                                  
CONECT   19   18                                                            
CONECT   20   18   22   48   21                                             
CONECT   21   22   20                                                       
CONECT   22   14   20   21   49                                             
CONECT   23   11   14   50   51                                             
CONECT   24   25    2   36                                                  
CONECT   25   24   26                                                       
CONECT   26   27   25                                                       
CONECT   27   36   26   35   28                                             
CONECT   28   27   29   52                                                  
CONECT   29   30   28   31                                                  
CONECT   30   29                                                            
CONECT   31   32   33   29                                                  
CONECT   32   31                                                            
CONECT   33   35   31   53   34                                             
CONECT   34   35   33                                                       
CONECT   35   33   34   27   54                                             
CONECT   36   24   27   55   56                                             
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47   15                                                            
CONECT   48   20                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   28                                                            
CONECT   53   33                                                            
CONECT   54   35                                                            
CONECT   55   36                                                            
CONECT   56   36                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

RDKit          3D

56 61  0  0  0  0  0  0  0  0999 V2000
   -0.6743    1.0166    1.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1170   -0.0567    1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -0.3782    1.6710 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0330    0.5639    2.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5122    0.2547    2.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9889    0.1723    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    1.4302   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981    1.4800   -0.6830 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553    2.6319   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    3.7416   -0.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902    2.4404   -1.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572    1.2800   -1.7233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    1.5063   -2.2653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8701    2.8495   -1.9323 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5285    3.4196   -3.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7356    4.0092   -3.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175    4.6914   -4.8090 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5763    4.1566   -1.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5991    4.8270   -1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1033    3.4624   -0.7566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9879    2.0329   -0.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681    2.7761   -0.7230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5817    3.6041   -1.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8467   -1.1790    0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -2.3095    0.3187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -3.0877   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -2.2164   -0.7226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1223   -1.7602   -2.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404   -1.7353   -3.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -1.0797   -4.8270 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4407   -2.2092   -2.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3556   -2.0379   -3.6852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7018   -2.9074   -1.6097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8865   -4.0774   -1.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6611   -2.9603   -0.5271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2725   -1.0428    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629   -1.3391    1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925    1.5820    2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975    0.5088    3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    1.0156    2.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -0.7034    2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708   -0.0101    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -0.7010    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    1.4187   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674    2.3360    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    0.6452   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590    3.3206   -4.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5028    3.8383    0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    2.6513    0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549    4.2699   -0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    4.1522   -2.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1144   -1.4096   -2.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7429   -2.9715   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524   -3.0972    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678   -1.1721    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -0.0777   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
 25 24  2  0
 29 30  1  0
 14 13  1  6
 24  2  1  0
 24 36  1  0
  2  3  1  0
 27 36  1  0
  3  4  1  0
 13 12  1  0
 12 11  2  0
 11 23  1  0
 14 23  1  0
 27 26  1  1
  4  5  1  0
 20 18  1  0
 22 14  1  0
 14 15  1  0
 15 16  2  0
 16 18  1  0
 31 32  2  0
 11  9  1  0
 33 35  1  0
  9  8  1  0
  8  7  1  0
 35 34  1  0
  7  6  1  0
  6  5  1  0
 26 25  1  0
 18 19  2  0
 20 22  1  0
 22 21  1  0
 33 31  1  0
 35 27  1  0
 27 28  1  0
 33 53  1  1
 20 48  1  1
 28 29  2  0
 22 49  1  1
 35 54  1  1
  9 10  2  0
 29 31  1  0
 16 17  1  0
 33 34  1  0
 20 21  1  0
 36 55  1  0
 36 56  1  0
 28 52  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
 23 50  1  0
 23 51  1  0
 15 47  1  0
  8 46  1  0
  7 44  1  0
  7 45  1  0
  6 42  1  0
  6 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀Br₂N₄O₈

Average Mass

628.2300 Da

Monoisotopic Mass

625.96479 Da

IUPAC Name

(1R,2S,6S)-4-bromo-N-(4-{[(1R,2S,6S)-4-bromo-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-en-4'-yl]formamido}butyl)-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-ene-4'-carboxamide

Traditional Name

(1R,2S,6S)-4-bromo-N-{4-[(1R,2S,6S)-4-bromo-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-en-4'-ylformamido]butyl}-5-oxo-3'H-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-[1,5]oxazol]-3-ene-4'-carboxamide

CAS Registry Number

Not Available

SMILES

[H]N(C(=O)C1=NO[C@]2(C([H])=C(Br)C(=O)[C@@]3([H])O[C@@]23[H])C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=O)C1=NO[C@]2(C([H])=C(Br)C(=O)[C@@]3([H])O[C@@]23[H])C1([H])[H]

InChI Identifier

InChI=1S/C22H20Br2N4O8/c23-9-5-21(17-15(33-17)13(9)29)7-11(27-35-21)19(31)25-3-1-2-4-26-20(32)12-8-22(36-28-12)6-10(24)14(30)16-18(22)34-16/h5-6,15-18H,1-4,7-8H2,(H,25,31)(H,26,32)/t15-,16-,17-,18-,21-,22-/m1/s1

InChI Key

OPMAEHVWCSXSKG-GARQETNWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-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
Aplysina gerardogreeni	JEOL database	Encarnacion, R. D., et al, J. Nat. Prod. 63, 874 (2000)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-haloketone
Isoxazoline
Carboxamide group
Oxime ether
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Vinyl bromide
Vinyl halide
Azacycle
Bromoalkene
Haloalkene
Organoheterocyclic compound
Organic nitrogen compound
Organic oxide
Organohalogen compound
Organobromide
Organonitrogen compound
Hydrocarbon derivative
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	2.05	ALOGPS
logP	1.58	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.96	ChemAxon
pKa (Strongest Basic)	0.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	160.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.11 m³·mol⁻¹	ChemAxon
Polarizability	50.9 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8683615

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10508214

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Encarnacion, R. D., et al. (2000). Encarnacion, R. D., et al, J. Nat. Prod. 63, 874 (2000). J. Nat. Prod..

Showing NP-Card for calafianin (NP0029182)

MOL for NP0029182 (calafianin)

3D MOL for NP0029182 (calafianin)

3D SDF for NP0029182 (calafianin)

3D-SDF for NP0029182 (calafianin)

PDB for NP0029182 (calafianin)

3D PDB for NP0029182 (calafianin)

SMILES for NP0029182 (calafianin)

INCHI for NP0029182 (calafianin)

Structure for NP0029182 (calafianin)

3D Structure for NP0029182 (calafianin)