NP-MRD: Showing NP-Card for Xylarisin (NP0008887)

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Record Information

Version

2.0

Created at

2020-12-09 06:22:50 UTC

Updated at

2021-07-15 17:01:43 UTC

NP-MRD ID

NP0008887

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xylarisin

Provided By

NPAtlas

Description

Xylarisin is found in Xylaria. Xylarisin was first documented in 2009 (PMID: 19952454).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106313D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242106313D          

 61 64  0  0  0  0            999 V2000
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    1.7867   -1.0720   -1.4643 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9401   -0.4282   -2.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919   -0.2275   -0.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.4968   -0.8693    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4377    0.1431   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.1063    1.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4898    2.1587    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720    1.1715   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944    3.0895   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084   -0.7227    2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -1.5021    1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -0.6115    3.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6984    1.7454    3.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6050    1.3196    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3854    0.4003    2.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4727   -1.6773    1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9336    1.1732   -0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2705   -0.3999   -3.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7695   -1.5067   -1.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    0.6333   -2.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -0.4713   -3.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.9503   -3.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179   -0.7630    0.5976 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
  2  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  2  0  0  0  0
  9  7  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28  5  1  0  0  0  0
 22  9  1  0  0  0  0
 25 23  1  0  0  0  0
 28  9  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  1  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  5 38  1  6  0  0  0
  6 39  1  0  0  0  0
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 17 48  1  0  0  0  0
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 18 50  1  1  0  0  0
 19 51  1  0  0  0  0
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 21 53  1  0  0  0  0
 22 54  1  1  0  0  0
 23 55  1  6  0  0  0
 25 56  1  6  0  0  0
 26 57  1  1  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 27 60  1  0  0  0  0
 28 61  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0008887

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO5/c1-11(2)9-16-18-12(3)19-20(28-19)15-8-7-13(24)5-4-6-14(25)10-17(26)22(15,18)21(27)23-16/h7-8,11-16,18-20,24-25H,4-6,9-10H2,1-3H3,(H,23,27)/b8-7-/t12-,13-,14-,15-,16-,18-,19+,20-,22+/m0/s1

> <INCHI_KEY>
GNNKACUJOHRGTR-WIJFAJTRSA-N

> <FORMULA>
C22H33NO5

> <MOLECULAR_WEIGHT>
391.508

> <EXACT_MASS>
391.235873167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.92273409109404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,8S,9Z,11R,12S,14R,15S,16R,17S)-4,8-dihydroxy-15-methyl-17-(2-methylpropyl)-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadec-9-ene-2,19-dione

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
1.567915408000001

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.111338048066436

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.13407638082267

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4937179492497994

> <JCHEM_POLAR_SURFACE_AREA>
99.16000000000001

> <JCHEM_REFRACTIVITY>
105.00690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,8S,9Z,11R,12S,14R,15S,16R,17S)-4,8-dihydroxy-15-methyl-17-(2-methylpropyl)-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadec-9-ene-2,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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    0.2857   -2.6951   -0.4407 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769   -2.2699   -1.6189 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7867   -1.0720   -1.4643 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9401   -0.4282   -2.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919   -0.2275   -0.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6584   -0.3670    2.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4377    0.1431   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.1063    1.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0042   -0.4713   -3.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.9503   -3.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179   -0.7630    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  9  7  1  6
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
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 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28  5  1  0
 22  9  1  0
 25 23  1  0
 28  9  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  1
 14 43  1  0
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 18 50  1  1
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 23 55  1  6
 25 56  1  6
 26 57  1  1
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  1
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       4.766   0.272   2.325  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.987   0.117   1.015  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.963   0.106  -0.142  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.929   1.184   0.908  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126   1.056  -0.332  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.110   2.088  -0.462  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.031   1.493  -1.088  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.743   2.009  -2.004  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.155   0.169  -0.413  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.555   0.415   1.011  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.318   1.521   1.471  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.205  -0.517   1.937  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.354   0.038   2.717  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.916   1.277   3.242  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.627   0.283   1.987  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.144  -0.773   1.114  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.255  -0.580  -0.344  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.554   0.567  -0.957  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.571   1.549  -1.226  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.907   0.360  -2.249  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.750  -0.253  -2.331  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.071  -0.752  -1.122  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.437  -2.076  -1.559  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.286  -2.695  -0.441  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.877  -2.270  -1.619  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.787  -1.072  -1.464  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.940  -0.428  -2.782  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.292  -0.228  -0.359  0.00  0.00           C+0
HETATM   29  H   UNK     0       5.658  -0.367   2.232  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.011   1.326   2.501  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.095  -0.131   3.114  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.497  -0.869   1.051  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.727   0.910  -0.017  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.503  -0.867  -0.092  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.438   0.143  -1.085  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.339   1.106   1.855  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.490   2.159   0.879  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.772   1.172  -1.210  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.194   3.090  -0.158  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.408  -0.723   2.728  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.473  -1.502   1.588  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.510  -0.612   3.606  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.698   1.745   3.650  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.605   1.320   1.599  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.385   0.400   2.838  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.133  -1.163   1.501  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.473  -1.677   1.288  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.053  -1.567  -0.848  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.364  -0.477  -0.579  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.934   1.173  -0.262  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.204   2.267  -1.775  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.337   0.695  -3.216  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.270  -0.400  -3.324  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.775  -1.133  -0.355  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.218  -2.782  -1.951  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.341  -3.036  -2.309  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.769  -1.507  -1.138  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.650   0.633  -2.835  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.004  -0.471  -3.123  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.363  -0.950  -3.585  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.518  -0.763   0.598  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3    4   32                                             
CONECT    3    2   33   34   35                                             
CONECT    4    2    5   36   37                                             
CONECT    5    4    6   28   38                                             
CONECT    6    5    7   39                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   22   28                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   40   41                                             
CONECT   13   12   14   15   42                                             
CONECT   14   13   43                                                       
CONECT   15   13   16   44   45                                             
CONECT   16   15   17   46   47                                             
CONECT   17   16   18   48   49                                             
CONECT   18   17   19   20   50                                             
CONECT   19   18   51                                                       
CONECT   20   18   21   52                                                  
CONECT   21   20   22   53                                                  
CONECT   22   21   23    9   54                                             
CONECT   23   22   24   25   55                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   23   56                                             
CONECT   26   25   27   28   57                                             
CONECT   27   26   58   59   60                                             
CONECT   28   26    5    9   61                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

RDKit          3D

61 64  0  0  0  0  0  0  0  0999 V2000
    4.7655    0.2724    2.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9869    0.1166    1.0148 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9625    0.1063   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    1.1839    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263    1.0560   -0.3319 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1100    2.0882   -0.4617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0306    1.4927   -1.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7427    2.0087   -2.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551    0.1687   -0.4128 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5548    0.4145    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175    1.5210    1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049   -0.5170    1.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3543    0.0375    2.7171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9157    1.2770    3.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.2825    1.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1436   -0.7726    1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555   -0.5798   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541    0.5673   -0.9571 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5711    1.5490   -1.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    0.3599   -2.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -0.2532   -2.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -0.7523   -1.1224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4367   -2.0760   -1.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2857   -2.6951   -0.4407 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769   -2.2699   -1.6189 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7867   -1.0720   -1.4643 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9401   -0.4282   -2.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919   -0.2275   -0.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6584   -0.3670    2.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0105    1.3260    2.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0950   -0.1305    3.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4968   -0.8693    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7266    0.9096   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026   -0.8673   -0.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4377    0.1431   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.1063    1.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4898    2.1587    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720    1.1715   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944    3.0895   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084   -0.7227    2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -1.5021    1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -0.6115    3.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6984    1.7454    3.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6050    1.3196    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3854    0.4003    2.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1329   -1.1630    1.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4727   -1.6773    1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0531   -1.5673   -0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640   -0.4772   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336    1.1732   -0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2042    2.2667   -1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.6952   -3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2705   -0.3999   -3.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7747   -1.1330   -0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179   -2.7816   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414   -3.0362   -2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695   -1.5067   -1.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    0.6333   -2.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -0.4713   -3.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.9503   -3.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179   -0.7630    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  9  7  1  6
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28  5  1  0
 22  9  1  0
 25 23  1  0
 28  9  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  1
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  1
 19 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  1
 23 55  1  6
 25 56  1  6
 26 57  1  1
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₅

Average Mass

391.5080 Da

Monoisotopic Mass

391.23587 Da

IUPAC Name

(1R,4S,8S,9Z,11R,12S,14R,15S,16R,17S)-4,8-dihydroxy-15-methyl-17-(2-methylpropyl)-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadec-9-ene-2,19-dione

Traditional Name

(1R,4S,8S,9Z,11R,12S,14R,15S,16R,17S)-4,8-dihydroxy-15-methyl-17-(2-methylpropyl)-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadec-9-ene-2,19-dione

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1NC(=O)[C@]23[C@H]1[C@H](C)[C@H]1O[C@H]1[C@@H]2\C=C/[C@@H](O)CCC[C@H](O)CC3=O

InChI Identifier

InChI=1S/C22H33NO5/c1-11(2)9-16-18-12(3)19-20(28-19)15-8-7-13(24)5-4-6-14(25)10-17(26)22(15,18)21(27)23-16/h7-8,11-16,18-20,24-25H,4-6,9-10H2,1-3H3,(H,23,27)/b8-7-/t12-,13-,14-,15-,16-,18-,19+,20-,22+/m0/s1

InChI Key

GNNKACUJOHRGTR-WIJFAJTRSA-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
Xylaria	NPAtlas	19952454

Chemical Taxonomy

Classification

Not classified

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	0.73	ALOGPS
logP	1.57	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.01 m³·mol⁻¹	ChemAxon
Polarizability	41.92 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

Rukachaisirikul V, Khamthong N, Sukpondma Y, Pakawatchai C, Phongpaichit S, Sakayaroj J, Kirtikara K: An [11]cytochalasin derivative from the marine-derived fungus Xylaria sp. PSU-F100. Chem Pharm Bull (Tokyo). 2009 Dec;57(12):1409-11. doi: 10.1248/cpb.57.1409. [PubMed:19952454 ]

Showing NP-Card for Xylarisin (NP0008887)

MOL for NP0008887 (Xylarisin)

3D MOL for NP0008887 (Xylarisin)

3D SDF for NP0008887 (Xylarisin)

3D-SDF for NP0008887 (Xylarisin)

PDB for NP0008887 (Xylarisin)

3D PDB for NP0008887 (Xylarisin)

SMILES for NP0008887 (Xylarisin)

INCHI for NP0008887 (Xylarisin)

Structure for NP0008887 (Xylarisin)

3D Structure for NP0008887 (Xylarisin)