NP-MRD: Showing NP-Card for Fumigaclavine C (NP0021093)

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Record Information

Version

1.0

Created at

2021-01-06 06:23:15 UTC

Updated at

2021-07-15 17:35:26 UTC

NP-MRD ID

NP0021093

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fumigaclavine C

Provided By

NPAtlas

Description

Fumigaclavine C is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Fumigaclavine C is found in Aspergillus fumigatus, Aspergullus fumigatus, Isaria tenuipes BCC12625, Neosartarya fumigata Af293 and Streptomyces piomogenus. It was first documented in 1977 (PMID: 328548). Based on a literature review a significant number of articles have been published on fumigaclavine C (PMID: 15231043) (PMID: 16023606) (PMID: 16397874) (PMID: 16557450).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120403D          

 57 60  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242120403D          

 57 60  0  0  0  0            999 V2000
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    3.5800    2.0174    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1812    1.2996    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387    0.5377    2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    0.0079   -1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    1.6404   -0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0726    0.3819   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3839    1.4188   -2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    2.2559   -4.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3517    2.3026   -3.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296    1.4535   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6622    0.5429    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255   -1.0515    1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830   -1.4077   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813    1.1966    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618    0.3608    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4444    2.5085   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6735    2.2872   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5100    3.6212   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346   -1.4125    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901   -2.5024   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -1.2223   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1052   -2.8083   -0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -1.6865    2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5364   -3.0803    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5980   -2.5869    2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -3.1151    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106   -3.6108    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14  6  2  0  0  0  0
 26 16  1  0  0  0  0
 13  8  1  0  0  0  0
 17 12  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  7 37  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 11 40  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 16 43  1  6  0  0  0
 17 44  1  1  0  0  0
 18 45  1  1  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 23 49  1  1  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 27 55  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C([H])C(C1=C2C3=C(C([H])=C([H])C([H])=C3N1[H])[C@@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])N(C([H])([H])[H])[C@]1([H])C2([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O2/c1-7-23(4,5)22-16-11-18-20(15-9-8-10-17(24-22)19(15)16)21(27-14(3)26)13(2)12-25(18)6/h7-10,13,18,20-21,24H,1,11-12H2,2-6H3/t13-,18+,20+,21-/m0/s1

> <INCHI_KEY>
OSICWVVWEXKSBD-LFAYTRTRSA-N

> <FORMULA>
C23H30N2O2

> <MOLECULAR_WEIGHT>
366.505

> <EXACT_MASS>
366.230728214

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.87514767911447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4S,7R)-4,6-dimethyl-10-(2-methylbut-3-en-2-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
3.845861202333333

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.445370057063926

> <JCHEM_PKA_STRONGEST_BASIC>
8.390647861190763

> <JCHEM_POLAR_SURFACE_AREA>
45.330000000000005

> <JCHEM_REFRACTIVITY>
109.04650000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,7R)-4,6-dimethyl-10-(2-methylbut-3-en-2-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    4.7613   -1.6754    1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848   -1.2296    0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9253    0.2072    0.1665 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1120    1.0499    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    0.5484   -0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938    0.5923   -0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    1.1716   -1.8012 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.3582   -2.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895    1.8780   -3.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916    1.8992   -3.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4798    1.4128   -2.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.8926   -0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    0.8908   -1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331    0.4051   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8316   -0.1964    1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -0.8025    0.7433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3679    0.3868    0.3077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8006    0.1423    0.4659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7116    0.9231   -0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804    1.7481    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6293    2.5617   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    1.8046    1.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -1.3627    0.4339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8653   -2.0009   -0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363   -1.9704    1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712   -1.5633    1.7819 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746   -2.7641    1.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313   -2.7134    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -0.9944    2.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4043   -1.9483   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800    2.0174    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1812    1.2996    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387    0.5377    2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    0.0079   -1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    1.6404   -0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0726    0.3819   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3839    1.4188   -2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    2.2559   -4.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3517    2.3026   -3.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296    1.4535   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6622    0.5429    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255   -1.0515    1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830   -1.4077   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813    1.1966    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618    0.3608    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4444    2.5085   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6735    2.2872   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5100    3.6212   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346   -1.4125    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901   -2.5024   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -1.2223   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1052   -2.8083   -0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -1.6865    2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5364   -3.0803    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5980   -2.5869    2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -3.1151    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106   -3.6108    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 14  6  2  0
 26 16  1  0
 13  8  1  0
 17 12  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  6
 17 44  1  1
 18 45  1  1
 21 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  1
 24 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  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       4.761  -1.675   1.444  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.985  -1.230   0.469  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.925   0.207   0.167  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.112   1.050   1.425  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.101   0.548  -0.738  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.694   0.592  -0.565  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.590   1.172  -1.801  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.279   1.358  -2.098  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.590   1.878  -3.174  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.792   1.899  -3.119  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.480   1.413  -2.013  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.813   0.893  -0.932  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.576   0.891  -1.035  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.433   0.405  -0.063  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.832  -0.196   1.190  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.519  -0.803   0.743  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.368   0.387   0.308  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.801   0.142   0.466  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.712   0.923  -0.234  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.680   1.748   0.328  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.629   2.562  -0.462  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.753   1.805   1.596  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.145  -1.363   0.434  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.865  -2.001  -0.866  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.436  -1.970   1.614  0.00  0.00           C+0
HETATM   26  N   UNK     0      -1.071  -1.563   1.782  0.00  0.00           N+0
HETATM   27  C   UNK     0      -0.275  -2.764   1.960  0.00  0.00           C+0
HETATM   28  H   UNK     0       4.831  -2.713   1.694  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.375  -0.994   2.047  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.404  -1.948  -0.089  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.580   2.017   1.271  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.181   1.300   1.564  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.739   0.538   2.322  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.033   0.008  -1.699  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.027   1.640  -0.973  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.073   0.382  -0.230  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.384   1.419  -2.396  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.123   2.256  -4.032  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.352   2.303  -3.954  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.530   1.454  -2.029  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.662   0.543   1.973  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.426  -1.052   1.562  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.283  -1.408  -0.148  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.081   1.197   1.069  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.062   0.361   1.562  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.444   2.509  -1.534  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.673   2.287  -0.180  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.510   3.621  -0.089  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.235  -1.413   0.640  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.790  -2.502  -1.279  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.616  -1.222  -1.616  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.105  -2.808  -0.835  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.994  -1.687   2.528  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.536  -3.080   1.508  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.598  -2.587   2.623  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.148  -3.115   0.987  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.911  -3.611   2.329  0.00  0.00           H+0
CONECT    1    2   28   29                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3   31   32   33                                             
CONECT    5    3   34   35   36                                             
CONECT    6    3    7   14                                                  
CONECT    7    6    8   37                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   38                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   12   40                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14    8                                                  
CONECT   14   13   15    6                                                  
CONECT   15   14   16   41   42                                             
CONECT   16   15   17   26   43                                             
CONECT   17   16   18   12   44                                             
CONECT   18   17   19   23   45                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   46   47   48                                             
CONECT   22   20                                                            
CONECT   23   18   24   25   49                                             
CONECT   24   23   50   51   52                                             
CONECT   25   23   26   53   54                                             
CONECT   26   25   27   16                                                  
CONECT   27   26   55   56   57                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   21                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
    4.7613   -1.6754    1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848   -1.2296    0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9253    0.2072    0.1665 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1120    1.0499    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    0.5484   -0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938    0.5923   -0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    1.1716   -1.8012 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.3582   -2.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895    1.8780   -3.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916    1.8992   -3.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4798    1.4128   -2.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.8926   -0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    0.8908   -1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331    0.4051   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8316   -0.1964    1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -0.8025    0.7433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3679    0.3868    0.3077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8006    0.1423    0.4659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7116    0.9231   -0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804    1.7481    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6293    2.5617   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    1.8046    1.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -1.3627    0.4339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8653   -2.0009   -0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363   -1.9704    1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712   -1.5633    1.7819 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746   -2.7641    1.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313   -2.7134    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -0.9944    2.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4043   -1.9483   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800    2.0174    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1812    1.2996    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387    0.5377    2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    0.0079   -1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    1.6404   -0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0726    0.3819   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3839    1.4188   -2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    2.2559   -4.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3517    2.3026   -3.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296    1.4535   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6622    0.5429    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255   -1.0515    1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830   -1.4077   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813    1.1966    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618    0.3608    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4444    2.5085   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6735    2.2872   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5100    3.6212   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346   -1.4125    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901   -2.5024   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -1.2223   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1052   -2.8083   -0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -1.6865    2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5364   -3.0803    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5980   -2.5869    2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484   -3.1151    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106   -3.6108    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 14  6  2  0
 26 16  1  0
 13  8  1  0
 17 12  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  6
 17 44  1  1
 18 45  1  1
 21 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  1
 24 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀N₂O₂

Average Mass

366.5050 Da

Monoisotopic Mass

366.23073 Da

IUPAC Name

(2R,3S,4S,7R)-4,6-dimethyl-10-(2-methylbut-3-en-2-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

Traditional Name

(2R,3S,4S,7R)-4,6-dimethyl-10-(2-methylbut-3-en-2-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1CN(C)[C@@H]2CC3=C(NC4=CC=CC([C@H]2[C@H]1OC(C)=O)=C34)C(C)(C)C=C

InChI Identifier

InChI=1S/C23H30N2O2/c1-7-23(4,5)22-16-11-18-20(15-9-8-10-17(24-22)19(15)16)21(27-14(3)26)13(2)12-25(18)6/h7-10,13,18,20-21,24H,1,11-12H2,2-6H3/t13-,18+,20+,21-/m0/s1

InChI Key

OSICWVVWEXKSBD-LFAYTRTRSA-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 fumigatus	NPAtlas	328548
Aspergullus fumigatus	-	KNApSAcK
Isaria tenuipes BCC12625	-	KNApSAcK
Neosartarya fumigata Af293	-	KNApSAcK
Streptomyces piomogenus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Neosartorya fumigata	KNApSAcK Database	22123792

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	4.31	ALOGPS
logP	3.85	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.05 m³·mol⁻¹	ChemAxon
Polarizability	42.88 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

NPAtlas ID

NPA018250

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011250

Chemspider ID

28184662

KEGG Compound ID

Not Available

BioCyc ID

CPD-12338

BiGG ID

Not Available

Wikipedia Link

Fumigaclavine C

METLIN ID

Not Available

PubChem Compound

57339223

PDB ID

Not Available

ChEBI ID

64673

Good Scents ID

Not Available

References

General References

Cole RJ, Kirksey JW, Dorner JW, Wilson DM, Johnson JC Jr, Johnson AN, Bedell DM, Springer JP, Chexal KK, Clardy JC, Cox RH: Mycotoxins produced by Aspergillus fumigatus species isolated from molded silage. J Agric Food Chem. 1977 Jul-Aug;25(4):826-30. doi: 10.1021/jf60212a015. [PubMed:328548 ]
Zhao Y, Liu J, Wang J, Wang L, Yin H, Tan R, Xu Q: Fumigaclavine C improves concanavalin A-induced liver injury in mice mainly via inhibiting TNF-alpha production and lymphocyte adhesion to extracellular matrices. J Pharm Pharmacol. 2004 Jun;56(6):775-82. doi: 10.1211/0022357023592. [PubMed:15231043 ]
Wu XF, Fei MJ, Shu RG, Tan RX, Xu Q: Fumigaclavine C, an fungal metabolite, improves experimental colitis in mice via downregulating Th1 cytokine production and matrix metalloproteinase activity. Int Immunopharmacol. 2005 Sep;5(10):1543-53. doi: 10.1016/j.intimp.2005.04.014. [PubMed:16023606 ]
Unsold IA, Li SM: Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: gene expression, purification, and characterization of fumigaclavine C synthase FGAPT1. Chembiochem. 2006 Jan;7(1):158-64. doi: 10.1002/cbic.200500318. [PubMed:16397874 ]
Ma HY, Song YC, Mao YY, Jiang JH, Tan RX, Luo L: Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings. Planta Med. 2006 Apr;72(5):387-92. doi: 10.1055/s-2005-916235. [PubMed:16557450 ]

Showing NP-Card for Fumigaclavine C (NP0021093)

MOL for NP0021093 (Fumigaclavine C)

3D MOL for NP0021093 (Fumigaclavine C)

3D SDF for NP0021093 (Fumigaclavine C)

3D-SDF for NP0021093 (Fumigaclavine C)

PDB for NP0021093 (Fumigaclavine C)

3D PDB for NP0021093 (Fumigaclavine C)

SMILES for NP0021093 (Fumigaclavine C)

INCHI for NP0021093 (Fumigaclavine C)

Structure for NP0021093 (Fumigaclavine C)

3D Structure for NP0021093 (Fumigaclavine C)