NP-MRD: Showing NP-Card for (2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione (NP0322412)

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Record Information

Version

2.0

Created at

2022-09-12 01:10:00 UTC

Updated at

2022-09-12 01:10:00 UTC

NP-MRD ID

NP0322412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione

Description

Demecolcinone belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group. (2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione is found in Colchicum szovitsii. (2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione was first documented in 2005 (PMID: 15730238). Based on a literature review a small amount of articles have been published on demecolcinone (PMID: 19177900) (PMID: 28959419).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203102D          

 25 29  0  0  1  0            999 V2000
    2.0802    1.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233    0.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9451   -0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -0.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1456   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -0.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601    0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9300   -0.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545    0.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3585   -0.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712   -1.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7315   -1.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527   -1.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402   -1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373   -2.2659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5967   -2.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690   -2.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -2.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -1.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236   -1.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9827   -1.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6353   -0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1857   -0.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214    0.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    0.7947    0.0000 O   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
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
    0.8166   -3.2724   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368   -2.2999    0.6337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233   -1.6039    0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8626   -0.2975    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    0.4029    0.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4210   -0.4247    1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7349   -0.4296    0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4017    0.5837   -0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6714    0.2687   -0.5455 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2705   -0.9704   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383    1.8467   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7338    2.6466   -0.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903    2.4078   -0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5527    1.7405    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    2.5391    0.1645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3144    2.4493   -1.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812    1.5252   -0.6661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7825    1.8193   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478    1.8722    0.7560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0765    0.5570    0.4084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2900   -0.2398    0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614   -1.5302    0.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6000   -2.2014    0.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1325   -2.2942    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173   -3.5401    0.7451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2148   -4.1794   -0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8393   -3.5732    0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9186   -2.8383   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248   -1.0560    1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2707   -1.3300    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7766   -1.7951   -0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3097   -1.2652    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3252   -0.9147   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803    3.4832   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5862    3.5518    0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086    3.4109   -1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6111    2.0138   -1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2096    0.8545   -1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2655    2.2278   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8001    2.4977   -1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2639    0.2857    0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -2.9283    1.5350 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
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  1
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24  3  1  0
 20  4  1  0
 14  5  1  0
 19 15  1  0
 20 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 15 35  1  1
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 23 42  1  0
M  END


  Mrv1652309122203102D          

 25 29  0  0  1  0            999 V2000
    2.0802    1.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233    0.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9451   -0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -0.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1456   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -0.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601    0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9300   -0.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545    0.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3585   -0.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712   -1.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7315   -1.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527   -1.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402   -1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373   -2.2659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5967   -2.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690   -2.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -2.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -1.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236   -1.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9827   -1.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6353   -0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1857   -0.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214    0.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    0.7947    0.0000 O   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
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0322412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C3=CC=C(OC)C(=O)C=C3[C@H]3CC4(C)N3C24C=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO5/c1-18-7-11-10-6-12(21)14(24-2)5-4-9(10)15-17(25-3)16(23)13(22)8-19(15,18)20(11)18/h4-6,8,11,22H,7H2,1-3H3/t11-,18?,19?,20?/m1/s1

> <INCHI_KEY>
JHQXILBWKAUJFN-VGENCSJCSA-N

> <FORMULA>
C19H17NO5

> <MOLECULAR_WEIGHT>
339.347

> <EXACT_MASS>
339.110672651

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.43975724328513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0^{2,5}.0^{4,6}.0^{6,11}]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione

> <JCHEM_LOGP>
0.04933669366666682

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.95192453562229

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.648875140019012

> <JCHEM_PKA_STRONGEST_BASIC>
1.19784151189566

> <JCHEM_POLAR_SURFACE_AREA>
75.84

> <JCHEM_REFRACTIVITY>
95.2293

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0^{2,5}.0^{4,6}.0^{6,11}]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       3.883   2.593   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.524   1.193   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.631  -0.062   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.277  -1.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.872  -1.436   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.470  -0.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.952   0.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.203  -0.499   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.555   0.238   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.869  -0.565   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.280  -2.037   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.699  -2.635   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.125  -3.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.608  -2.788   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.856  -4.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.847  -5.500   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.489  -4.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.147  -5.338   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.532  -3.730   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.404  -2.855   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.834  -2.593   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.186  -1.175   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.347  -1.023   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.093   0.081   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.457   1.483   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17   15   20                                                  
CONECT   20   19    4   17   21                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₇NO₅

Average Mass

339.3470 Da

Monoisotopic Mass

339.11067 Da

IUPAC Name

(2R)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0^{2,5}.0^{4,6}.0^{6,11}]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione

Traditional Name

(2R)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0^{2,5}.0^{4,6}.0^{6,11}]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione

CAS Registry Number

Not Available

SMILES

COC1=C2C3=CC=C(OC)C(=O)C=C3[C@H]3CC4(C)N3C24C=C(O)C1=O

InChI Identifier

InChI=1S/C19H17NO5/c1-18-7-11-10-6-12(21)14(24-2)5-4-9(10)15-17(25-3)16(23)13(22)8-19(15,18)20(11)18/h4-6,8,11,22H,7H2,1-3H3/t11-,18?,19?,20?/m1/s1

InChI Key

JHQXILBWKAUJFN-VGENCSJCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Colchicum szovitsii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Not Available

Direct Parent

Tropones

Alternative Parents

Substituents

Tropone
Alkyl aryl ether
Azepine
Aralkylamine
Pyrrolidine
Vinylaziridine
Azetidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Azacycle
Ether
Enol
Aziridine
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.049	ChemAxon
pKa (Strongest Acidic)	8.65	ChemAxon
pKa (Strongest Basic)	1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.23 m³·mol⁻¹	ChemAxon
Polarizability	34.44 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00027139

Chemspider ID

24692292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44583926

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Alali FQ, Tahboub YR, Al-Daraysih IS, El-Elimat T: LC-MS and LC-PDA vs. phytochemical analysis of Colchicum brachyphyllum. Pharmazie. 2008 Dec;63(12):860-5. [PubMed:19177900 ]
Alali FQ, El-Elimat T, Li C, Qandil A, Alkofahi A, Tawaha K, Burgess JP, Nakanishi Y, Kroll DJ, Navarro HA, Falkinham JO 3rd, Wani MC, Oberlies NH: New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid. J Nat Prod. 2005 Feb;68(2):173-8. doi: 10.1021/np0496587. [PubMed:15730238 ]
Chen B, Liu X, Hu YJ, Zhang DM, Deng L, Lu J, Min L, Ye WC, Li CC: Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids. Chem Sci. 2017 Jul 1;8(7):4961-4966. doi: 10.1039/c7sc01341h. Epub 2017 May 5. [PubMed:28959419 ]
LOTUS database [Link]

Showing NP-Card for (2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione (NP0322412)

MOL for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

3D MOL for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

3D SDF for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

3D-SDF for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

PDB for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

3D PDB for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

SMILES for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

INCHI for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

Structure for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)

3D Structure for NP0322412 ((2r)-8-hydroxy-10,15-dimethoxy-4-methyl-5-azapentacyclo[10.5.0.0²,⁵.0⁴,⁶.0⁶,¹¹]heptadeca-1(17),7,10,12,14-pentaene-9,16-dione)