NP-MRD: Showing NP-Card for 9-hydroxyfumitremorgin C (NP0010652)

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Record Information

Version

2.0

Created at

2021-01-05 20:05:58 UTC

Updated at

2021-07-15 17:06:42 UTC

NP-MRD ID

NP0010652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxyfumitremorgin C

Provided By

NPAtlas

Description

9-hydroxyfumitremorgin C is found in Aspergillus and Aspergillus fumigatus. 9-hydroxyfumitremorgin C was first documented in 2012 (PMID: 22344914). Based on a literature review very few articles have been published on 9-hydroxyfumitremorgin C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107403D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242107403D          

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   -1.2191    3.3881   -1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    3.2090   -1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2253    4.7899   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -0.7407   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1928    0.6164    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8820   -0.1671   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736   -1.4610    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7487   -1.7297    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -2.8728   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7831   -3.5104    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1608   -1.1222   -1.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -0.9241    2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337   -2.5744    1.4093 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  3  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  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  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 11  3  1  0  0  0  0
 27 17  1  0  0  0  0
 10  6  1  0  0  0  0
 24 20  1  0  0  0  0
 29  7  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5 34  1  0  0  0  0
  9 35  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  6  0  0  0
 13 38  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 20 45  1  6  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 28 52  1  0  0  0  0
 29 53  1  0  0  0  0
 29 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12N(C(=O)[C@@]3([H])N(C1=O)C([H])([H])C([H])([H])C3([H])[H])[C@@]([H])(C([H])=C(C([H])([H])[H])C([H])([H])[H])C1=C(C3=C([H])C([H])=C(OC([H])([H])[H])C([H])=C3N1[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H25N3O4/c1-12(2)9-18-19-15(14-7-6-13(29-3)10-16(14)23-19)11-22(28)21(27)24-8-4-5-17(24)20(26)25(18)22/h6-7,9-10,17-18,23,28H,4-5,8,11H2,1-3H3/t17-,18-,22+/m0/s1

> <INCHI_KEY>
GAQLGONAVPUXSP-NPPFBWRTSA-N

> <FORMULA>
C22H25N3O4

> <MOLECULAR_WEIGHT>
395.459

> <EXACT_MASS>
395.184506297

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.638519904271675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12S,15S)-1-hydroxy-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4,6,8-tetraene-14,20-dione

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.846766038333334

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.117703671910043

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.015309115245449

> <JCHEM_PKA_STRONGEST_BASIC>
-4.541687097005739

> <JCHEM_POLAR_SURFACE_AREA>
85.87

> <JCHEM_REFRACTIVITY>
108.22259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,12S,15S)-1-hydroxy-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4,6,8-tetraene-14,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    7.4448   -0.4029   -0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641   -1.3638    0.1106 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2843   -1.2730    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905   -2.2699    0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -2.2533    1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781   -1.1878    0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1576   -0.8638    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002    0.3330   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245    0.7248   -0.4389 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -0.1771   -0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389   -0.2196   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    0.9574   -0.2104 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5244    2.0571    0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187    3.3419    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    4.4442    1.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431    3.6986   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072   -0.0261   -0.1333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7713    0.3529   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0815    1.5412   -0.0143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8277   -0.6322   -0.6103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1894   -0.2780   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6985   -1.5140    0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8157   -2.6056    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5477   -1.9259   -0.0451 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -2.2816    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -3.3965    0.8891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050   -1.4230    0.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4839   -1.8706   -1.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -1.5290    1.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5260   -0.5780   -1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1064    0.6408   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4752   -0.4578   -0.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1531   -3.1099    1.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817   -3.0377    1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.6002   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.5874   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525    1.4107   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529    1.8184    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569    5.0424    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430    4.0835    2.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    5.1413    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2191    3.3881   -1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    3.2090   -1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2253    4.7899   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -0.7407   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1928    0.6164    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8820   -0.1671   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736   -1.4610    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7487   -1.7297    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -2.8728   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7831   -3.5104    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1608   -1.1222   -1.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -0.9241    2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337   -2.5744    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  6
 27 29  1  0
 11  3  1  0
 27 17  1  0
 10  6  1  0
 24 20  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  6
 13 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 20 45  1  6
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  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       7.445  -0.403  -0.532  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.664  -1.364   0.111  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.284  -1.273   0.250  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.590  -2.270   0.901  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.231  -2.253   1.079  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.478  -1.188   0.590  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.158  -0.864   0.592  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.000   0.333  -0.052  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.224   0.725  -0.439  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.148  -0.177  -0.065  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.539  -0.220  -0.233  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.364   0.957  -0.210  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.524   2.057   0.755  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.519   3.342   0.393  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.681   4.444   1.369  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.343   3.699  -1.045  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.407  -0.026  -0.133  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.771   0.353  -0.239  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.082   1.541  -0.014  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.828  -0.632  -0.610  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.189  -0.278  -0.094  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.699  -1.514   0.647  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.816  -2.606   0.028  0.00  0.00           C+0
HETATM   24  N   UNK     0      -3.548  -1.926  -0.045  0.00  0.00           N+0
HETATM   25  C   UNK     0      -2.247  -2.282   0.310  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.031  -3.397   0.889  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.105  -1.423   0.045  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.484  -1.871  -1.141  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.038  -1.529   1.126  0.00  0.00           C+0
HETATM   30  H   UNK     0       7.526  -0.578  -1.621  0.00  0.00           H+0
HETATM   31  H   UNK     0       7.106   0.641  -0.355  0.00  0.00           H+0
HETATM   32  H   UNK     0       8.475  -0.458  -0.082  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.153  -3.110   1.290  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.682  -3.038   1.591  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.447   1.600  -0.957  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.043   0.587  -0.751  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.353   1.411  -1.237  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.653   1.818   1.803  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.257   5.042   1.379  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.943   4.083   2.378  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.476   5.141   0.982  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.219   3.388  -1.645  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.598   3.209  -1.372  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.225   4.790  -1.172  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.794  -0.741  -1.711  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.193   0.616   0.540  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.882  -0.167  -0.979  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.474  -1.461   1.731  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.749  -1.730   0.436  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.207  -2.873  -0.978  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.783  -3.510   0.670  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.161  -1.122  -1.667  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.397  -0.924   2.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.134  -2.574   1.409  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6   34                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   35                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10    3   36                                                  
CONECT   12    8   13   17   37                                             
CONECT   13   12   14   38                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   39   40   41                                             
CONECT   16   14   42   43   44                                             
CONECT   17   12   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24   45                                             
CONECT   21   20   22   46   47                                             
CONECT   22   21   23   48   49                                             
CONECT   23   22   24   50   51                                             
CONECT   24   23   25   20                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   17                                             
CONECT   28   27   52                                                       
CONECT   29   27    7   53   54                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    9                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   28                                                            
CONECT   53   29                                                            
CONECT   54   29                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  116    0
END

RDKit          3D

54 58  0  0  0  0  0  0  0  0999 V2000
    7.4448   -0.4029   -0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5905   -2.2699    0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -2.2533    1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1576   -0.8638    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1482   -0.1771   -0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389   -0.2196   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0815    1.5412   -0.0143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8277   -0.6322   -0.6103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1894   -0.2780   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6985   -1.5140    0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8157   -2.6056    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5477   -1.9259   -0.0451 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -2.2816    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -3.3965    0.8891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050   -1.4230    0.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4839   -1.8706   -1.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -1.5290    1.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5260   -0.5780   -1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1064    0.6408   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4752   -0.4578   -0.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1531   -3.1099    1.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817   -3.0377    1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.6002   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.5874   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525    1.4107   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529    1.8184    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569    5.0424    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430    4.0835    2.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    5.1413    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2191    3.3881   -1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    3.2090   -1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2253    4.7899   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -0.7407   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1928    0.6164    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8820   -0.1671   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736   -1.4610    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7487   -1.7297    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -2.8728   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7831   -3.5104    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1608   -1.1222   -1.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -0.9241    2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337   -2.5744    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  6
 27 29  1  0
 11  3  1  0
 27 17  1  0
 10  6  1  0
 24 20  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  6
 13 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 20 45  1  6
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅N₃O₄

Average Mass

395.4590 Da

Monoisotopic Mass

395.18451 Da

IUPAC Name

(1R,12S,15S)-1-hydroxy-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4,6,8-tetraene-14,20-dione

Traditional Name

(1R,12S,15S)-1-hydroxy-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4,6,8-tetraene-14,20-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1=C(N2)[C@H](C=C(C)C)N2C(=O)[C@@H]3CCCN3C(=O)[C@]2(O)C1

InChI Identifier

InChI=1S/C22H25N3O4/c1-12(2)9-18-19-15(14-7-6-13(29-3)10-16(14)23-19)11-22(28)21(27)24-8-4-5-17(24)20(26)25(18)22/h6-7,9-10,17-18,23,28H,4-5,8,11H2,1-3H3/t17-,18-,22+/m0/s1

InChI Key

GAQLGONAVPUXSP-NPPFBWRTSA-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
Aspergillus	NPAtlas	22344914
Aspergillus fumigatus	LOTUS Database	35616633

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	1.52	ALOGPS
logP	1.85	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.02	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.87 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.22 m³·mol⁻¹	ChemAxon
Polarizability	43.64 Å³	ChemAxon
Number of Rings	5	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

NPA017167

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29214104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587870

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Y, Li ZL, Bai J, Zhang LM, Wu X, Zhang L, Pei YH, Jing YK, Hua HM: 2,5-diketopiperazines from the marine-derived fungus Aspergillus fumigatus YK-7. Chem Biodivers. 2012 Feb;9(2):385-93. doi: 10.1002/cbdv.201100061. [PubMed:22344914 ]

Showing NP-Card for 9-hydroxyfumitremorgin C (NP0010652)

MOL for NP0010652 (9-hydroxyfumitremorgin C)

3D MOL for NP0010652 (9-hydroxyfumitremorgin C)

3D SDF for NP0010652 (9-hydroxyfumitremorgin C)

3D-SDF for NP0010652 (9-hydroxyfumitremorgin C)

PDB for NP0010652 (9-hydroxyfumitremorgin C)

3D PDB for NP0010652 (9-hydroxyfumitremorgin C)

SMILES for NP0010652 (9-hydroxyfumitremorgin C)

INCHI for NP0010652 (9-hydroxyfumitremorgin C)

Structure for NP0010652 (9-hydroxyfumitremorgin C)

3D Structure for NP0010652 (9-hydroxyfumitremorgin C)