NP-MRD: Showing NP-Card for Viridicatumtoxin A (NP0331320)

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Record Information

Version

1.0

Created at

2022-12-22 17:09:42 UTC

Updated at

2024-04-19 09:37:23 UTC

NP-MRD ID

NP0331320

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Viridicatumtoxin A

Description

Viridicatumtoxin, also known as NSC 159628 or SC 28762, belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups. Viridicatumtoxin 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. It was first documented in 2015 (PMID: 26058014). Based on a literature review a significant number of articles have been published on viridicatumtoxin (PMID: 28256128) (PMID: 32437130) (PMID: 32269157) (PMID: 27049441).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122443D          

 72 77  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 20 55  1  0
 21 56  1  0
 21 57  1  0
  9 47  1  0
 25 64  1  6
 29 67  1  0
 29 68  1  0
 31 69  1  0
 26 65  1  0
  4 45  1  0
 16 48  1  0
 16 49  1  0
 23 58  1  0
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 24 63  1  0
  1 42  1  0
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  1 44  1  0
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 34 70  1  0
 34 71  1  0
  6 46  1  0
 39 72  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
M  END


  Mrv1652306202122443D          

 72 77  0  0  0  0            999 V2000
   -0.2551   -4.9109   -3.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0698   -3.5455   -2.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422   -3.1949   -1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6129   -4.0885   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8116   -3.6392    0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1632   -4.5787    1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737   -2.2787    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -1.6648    2.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -2.4912    3.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9964   -0.7319   -2.4530 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.2529    2.0470    1.5247 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.8996    2.6335    2.8025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4123    3.9893    2.9537 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4621    3.2752    3.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3239    3.1675    6.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9561    1.8220    4.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4861    0.2199   -5.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4315    0.4628   -3.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1832    1.4156   -2.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4605   -1.9443   -3.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.8949   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050   -2.2457   -4.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9474   -0.7277   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723   -1.4698   -0.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886    2.5446    0.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0  0  0  0
 38 40  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0331320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(OC([H])([H])[H])=C2C3=C1C(O[H])=C1C(=O)[C@]4(O[H])C(=O)C(C(=O)N([H])[H])=C(O[H])C([H])([H])[C@]4(O[H])[C@@]([H])(O[H])C1=C3C([H])([H])[C@]21C(=C([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H31NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,23,32-35,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t23-,28-,29-,30+/m0/s1

> <INCHI_KEY>
SUWQGLGDFGHZNH-WBWZXODPSA-N

> <FORMULA>
C30H31NO10

> <MOLECULAR_WEIGHT>
565.575

> <EXACT_MASS>
565.194796202

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
57.69747806057729

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3'S,4'S,9'S)-3',4',6',9',12',14'-hexahydroxy-16'-methoxy-2,6,6-trimethyl-8',10'-dioxospiro[cyclohexane-1,18'-pentacyclo[11.6.1.0^{2,11}.0^{4,9}.0^{17,20}]icosane]-1',2,6',11',13'(20'),14',16'-heptaene-7'-carboxamide

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.4413639969999992

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.827835597921131

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.745728884255202

> <JCHEM_PKA_STRONGEST_BASIC>
-1.389926362581447

> <JCHEM_POLAR_SURFACE_AREA>
207.83999999999997

> <JCHEM_REFRACTIVITY>
147.1191

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3'S,4'S,9'S)-3',4',6',9',12',14'-hexahydroxy-16'-methoxy-2,6,6-trimethyl-8',10'-dioxospiro[cyclohexane-1,18'-pentacyclo[11.6.1.0^{2,11}.0^{4,9}.0^{17,20}]icosane]-1',2,6',11',13'(20'),14',16'-heptaene-7'-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 77  0  0  0  0  0  0  0  0999 V2000
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   -0.0698   -3.5455   -2.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1632   -4.5787    1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6154    1.4821   -5.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4315    0.4628   -3.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1832    1.4156   -2.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4605   -1.9443   -3.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.8949   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050   -2.2457   -4.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.2924   -0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -0.7277   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723   -1.4698   -0.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886    2.5446    0.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452    1.9784    2.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202    3.9859    2.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8412    1.7774    2.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019    3.5174    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8766    3.4547    4.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780    3.3350    8.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    2.9081    7.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1318    1.6942    5.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  0
 30 32  2  0
 32 36  1  0
 10 11  1  0
 30 31  1  0
 19 20  1  0
 25 26  1  0
 11 25  1  0
  7 13  2  0
 25 27  1  0
 14  3  2  0
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 38 40  1  0
  4  5  2  0
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 40 10  1  0
 21 22  1  0
 36 37  2  0
 13 12  1  0
 12 16  1  0
 15 16  1  0
 15 14  1  0
 40 41  2  0
 22 23  1  6
  8  9  1  0
 22 24  1  0
 38 27  1  0
  3  2  1  0
 12 11  2  0
  2  1  1  0
 15 17  1  6
 27 28  1  1
 10  8  2  0
 32 33  1  0
  8  7  1  0
 33 34  1  0
 15 22  1  0
 33 35  2  0
 17 19  2  0
  5  6  1  0
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  6 46  1  0
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 18 50  1  0
 18 51  1  0
 18 52  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.255  -4.911  -3.239  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.070  -3.546  -2.890  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.242  -3.195  -1.581  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.613  -4.088  -0.564  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.812  -3.639   0.748  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.163  -4.579   1.681  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.674  -2.279   1.088  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.861  -1.665   2.349  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.206  -2.491   3.397  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.700  -0.268   2.507  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.386   0.551   1.401  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.184  -0.074   0.167  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.312  -1.434   0.036  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.056  -1.847  -1.260  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.423  -0.668  -2.131  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.105   0.556  -1.168  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.412  -0.442  -3.409  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.889  -0.756  -3.379  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.133   0.075  -4.528  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.568   0.477  -4.681  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.359   0.468  -3.373  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.996  -0.732  -2.453  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.428  -2.027  -3.188  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.886  -0.652  -1.187  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.253   2.047   1.525  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.147   2.367   1.518  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.900   2.634   2.803  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.412   3.989   2.954  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.432   2.700   2.691  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.129   2.938   4.011  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.462   3.275   3.833  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.535   2.851   5.223  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.324   3.167   6.450  0.00  0.00           C+0
HETATM   34  N   UNK     0      -2.671   3.123   7.637  0.00  0.00           N+0
HETATM   35  O   UNK     0      -4.517   3.457   6.396  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.107   2.420   5.277  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.446   2.502   6.319  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.482   1.812   4.022  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.956   1.822   4.155  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.884   0.352   3.848  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.318  -0.338   4.769  0.00  0.00           O+0
HETATM   42  H   UNK     0       0.465  -5.552  -2.720  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.072  -5.008  -4.313  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.284  -5.231  -3.047  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.759  -5.146  -0.755  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.262  -4.101   2.531  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.348  -1.936   4.199  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.789   1.110  -1.484  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.920   1.278  -1.095  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.066  -1.834  -3.365  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.406  -0.357  -4.259  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.369  -0.310  -2.502  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.486   0.220  -5.412  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.040  -0.198  -5.405  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.615   1.482  -5.116  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.432   0.463  -3.610  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.183   1.416  -2.850  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.461  -1.944  -3.548  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.407  -2.895  -2.521  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.805  -2.246  -4.060  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.772   0.292  -0.647  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.947  -0.728  -1.454  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.672  -1.470  -0.491  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.689   2.545   0.650  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.545   1.978   2.325  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.520   3.986   2.648  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.841   1.777   2.262  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.702   3.517   2.008  0.00  0.00           H+0
HETATM   69  H   UNK     0      -4.877   3.455   4.710  0.00  0.00           H+0
HETATM   70  H   UNK     0      -3.178   3.335   8.486  0.00  0.00           H+0
HETATM   71  H   UNK     0      -1.678   2.908   7.702  0.00  0.00           H+0
HETATM   72  H   UNK     0       1.132   1.694   5.114  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2    3    1                                                       
CONECT    3   14    4    2                                                  
CONECT    4    3    5   45                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5   46                                                       
CONECT    7   13    5    8                                                  
CONECT    8    9   10    7                                                  
CONECT    9    8   47                                                       
CONECT   10   11   40    8                                                  
CONECT   11   10   25   12                                                  
CONECT   12   13   16   11                                                  
CONECT   13    7   14   12                                                  
CONECT   14    3   13   15                                                  
CONECT   15   16   14   17   22                                             
CONECT   16   12   15   48   49                                             
CONECT   17   15   19   18                                                  
CONECT   18   17   50   51   52                                             
CONECT   19   20   17   53                                                  
CONECT   20   19   21   54   55                                             
CONECT   21   20   22   56   57                                             
CONECT   22   21   23   24   15                                             
CONECT   23   22   58   59   60                                             
CONECT   24   22   61   62   63                                             
CONECT   25   26   11   27   64                                             
CONECT   26   25   65                                                       
CONECT   27   25   38   28   29                                             
CONECT   28   27   66                                                       
CONECT   29   30   27   67   68                                             
CONECT   30   29   32   31                                                  
CONECT   31   30   69                                                       
CONECT   32   30   36   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   70   71                                                  
CONECT   35   33                                                            
CONECT   36   32   37   38                                                  
CONECT   37   36                                                            
CONECT   38   40   27   36   39                                             
CONECT   39   38   72                                                       
CONECT   40   38   10   41                                                  
CONECT   41   40                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    4                                                            
CONECT   46    6                                                            
CONECT   47    9                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   21                                                            
CONECT   57   21                                                            
CONECT   58   23                                                            
CONECT   59   23                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   24                                                            
CONECT   63   24                                                            
CONECT   64   25                                                            
CONECT   65   26                                                            
CONECT   66   28                                                            
CONECT   67   29                                                            
CONECT   68   29                                                            
CONECT   69   31                                                            
CONECT   70   34                                                            
CONECT   71   34                                                            
CONECT   72   39                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  154    0
END

RDKit          3D

72 77  0  0  0  0  0  0  0  0999 V2000
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   -0.8607   -1.6648    2.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -2.4912    3.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.2680    2.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    0.5513    1.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844   -0.0736    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117   -1.4343    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559   -1.8465   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233   -0.6683   -2.1308 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.1286    2.9381    4.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4621    3.2752    3.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3239    3.1675    6.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713    3.1234    7.6373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5174    3.4568    6.3961 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4461    2.5025    6.3185 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9561    1.8220    4.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8836    0.3517    3.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181   -0.3382    4.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4650   -5.5522   -2.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9199    1.2782   -1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0660   -1.8338   -3.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4315    0.4628   -3.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1832    1.4156   -2.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4605   -1.9443   -3.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.8949   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050   -2.2457   -4.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.2924   -0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -0.7277   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723   -1.4698   -0.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886    2.5446    0.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452    1.9784    2.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202    3.9859    2.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8412    1.7774    2.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019    3.5174    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8766    3.4547    4.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780    3.3350    8.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    2.9081    7.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1318    1.6942    5.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  0
 30 32  2  0
 32 36  1  0
 10 11  1  0
 30 31  1  0
 19 20  1  0
 25 26  1  0
 11 25  1  0
  7 13  2  0
 25 27  1  0
 14  3  2  0
 20 21  1  0
  3  4  1  0
 38 40  1  0
  4  5  2  0
  5  7  1  0
 14 13  1  0
 40 10  1  0
 21 22  1  0
 36 37  2  0
 13 12  1  0
 12 16  1  0
 15 16  1  0
 15 14  1  0
 40 41  2  0
 22 23  1  6
  8  9  1  0
 22 24  1  0
 38 27  1  0
  3  2  1  0
 12 11  2  0
  2  1  1  0
 15 17  1  6
 27 28  1  1
 10  8  2  0
 32 33  1  0
  8  7  1  0
 33 34  1  0
 15 22  1  0
 33 35  2  0
 17 19  2  0
  5  6  1  0
 38 36  1  0
 38 39  1  1
 27 29  1  0
 17 18  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
  9 47  1  0
 25 64  1  6
 29 67  1  0
 29 68  1  0
 31 69  1  0
 26 65  1  0
  4 45  1  0
 16 48  1  0
 16 49  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 24 63  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
 28 66  1  0
 34 70  1  0
 34 71  1  0
  6 46  1  0
 39 72  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
M  END

View in JSmol

Synonyms

Value	Source
NSC 159628	ChEBI
SC 28762	ChEBI
Viridicatumtoxin a	ChEBI

Chemical Formula

C₃₀H₃₁NO₁₀

Average Mass

565.5750 Da

Monoisotopic Mass

565.19480 Da

IUPAC Name

(1S,3'S,4'S,9'S)-3',4',6',9',12',14'-hexahydroxy-16'-methoxy-2,6,6-trimethyl-8',10'-dioxospiro[cyclohexane-1,18'-pentacyclo[11.6.1.0^{2,11}.0^{4,9}.0^{17,20}]icosane]-1',2,6',11',13'(20'),14',16'-heptaene-7'-carboxamide

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(OC([H])([H])[H])=C2C3=C1C(O[H])=C1C(=O)[C@]4(O[H])C(=O)C(C(=O)N([H])[H])=C(O[H])C([H])([H])[C@]4(O[H])[C@@]([H])(O[H])C1=C3C([H])([H])[C@]21C(=C([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C30H31NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,23,32-35,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t23-,28-,29-,30+/m0/s1

InChI Key

SUWQGLGDFGHZNH-WBWZXODPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CDCl3, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.09 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.91 MHz, CDCl₃, 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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tetracyclines

Sub Class

Not Available

Direct Parent

Tetracyclines

Alternative Parents

Substituents

Tetracycline
Anthracene carboxylic acid or derivatives
1-naphthol
Naphthalene
Tetralin
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Benzenoid
Vinylogous acid
Tertiary alcohol
Carboxamide group
Ketone
Primary carboxylic acid amide
Secondary alcohol
Ether
Enol
Carboxylic acid derivative
Polyol
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:85616 )
tertiary alcohol (CHEBI:85616 )
aromatic ether (CHEBI:85616 )
secondary alcohol (CHEBI:85616 )
enone (CHEBI:85616 )
polyphenol (CHEBI:85616 )
spiro compound (CHEBI:85616 )
enamide (CHEBI:85616 )
polyketide (CHEBI:85616 )
aromatic ketone (CHEBI:85616 )
enol (CHEBI:85616 )
organic polycyclic compound (CHEBI:85616 )

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	1.1	ALOGPS
logP	1.44	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	207.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	147.12 m³·mol⁻¹	ChemAxon
Polarizability	57.7 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23354402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Viridicatumtoxin A

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

85616

Good Scents ID

Not Available

References

General References

Liu Y, Mandi A, Li XM, Meng LH, Kurtan T, Wang BG: Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides. Mar Drugs. 2015 Jun 5;13(6):3640-52. doi: 10.3390/md13063640. [PubMed:26058014 ]
Nicolaou KC, Liu G, Beabout K, McCurry MD, Shamoo Y: Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (-)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents. J Am Chem Soc. 2017 Mar 15;139(10):3736-3746. doi: 10.1021/jacs.6b12654. Epub 2017 Mar 3. [PubMed:28256128 ]
Li W, Li L, Zhang C, Cai Y, Gao Q, Wang F, Cao Y, Lin J, Li J, Shang Z, Lin W: Investigations into the Antibacterial Mechanism of Action of Viridicatumtoxins. ACS Infect Dis. 2020 Jul 10;6(7):1759-1769. doi: 10.1021/acsinfecdis.0c00031. Epub 2020 Jun 4. [PubMed:32437130 ]
Drott MT, Bastos RW, Rokas A, Ries LNA, Gabaldon T, Goldman GH, Keller NP, Greco C: Diversity of Secondary Metabolism in Aspergillus nidulans Clinical Isolates. mSphere. 2020 Apr 8;5(2):e00156-20. doi: 10.1128/mSphere.00156-20. [PubMed:32269157 ]
Inokoshi J, Nakamura Y, Komada S, Komatsu K, Umeyama H, Tomoda H: Inhibition of bacterial undecaprenyl pyrophosphate synthase by small fungal molecules. J Antibiot (Tokyo). 2016 Nov;69(11):798-805. doi: 10.1038/ja.2016.35. Epub 2016 Apr 6. [PubMed:27049441 ]

Showing NP-Card for Viridicatumtoxin A (NP0331320)

MOL for NP0331320 (Viridicatumtoxin A)

3D MOL for NP0331320 (Viridicatumtoxin A)

3D SDF for NP0331320 (Viridicatumtoxin A)

3D-SDF for NP0331320 (Viridicatumtoxin A)

PDB for NP0331320 (Viridicatumtoxin A)

3D PDB for NP0331320 (Viridicatumtoxin A)

SMILES for NP0331320 (Viridicatumtoxin A)

INCHI for NP0331320 (Viridicatumtoxin A)

Structure for NP0331320 (Viridicatumtoxin A)

3D Structure for NP0331320 (Viridicatumtoxin A)