NP-MRD: Showing NP-Card for n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid (NP0309403)

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Record Information

Version

2.0

Created at

2022-09-11 03:58:48 UTC

Updated at

2022-09-11 03:58:48 UTC

NP-MRD ID

NP0309403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid

Description

N-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]Hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid belongs to the class of organic compounds known as lumicolchicine alkaloids. These are alkaloids with a structure based on the tetracyclic lumicolchicine skeleton. They can derive from a colchicine precursor where the cycloheptatriene ring is replaced with a bicyclo[3.2.0]Hepta-2,6-diene ring system. n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid is found in Colchicum arenarium, Colchicum autumnale, Colchicum bivonae, Colchicum laetum, Colchicum raddeanum, Colchicum szovitsii, Colchicum turcicum, Gloriosa superba, Colchicum robustum and Wurmbea dioica. N-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]Hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520152D          

 29 32  0  0  0  0            999 V2000
    4.9272    1.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2091    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951    1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140    2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4194    2.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    2.6522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9033    2.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844    1.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675    1.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678    2.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368    3.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8226    3.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    3.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    4.0737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392    4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1365    5.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    5.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7227    2.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135    1.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039    1.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947    0.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045    0.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952   -0.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4768    1.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0765    0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670    0.7438    0.0000 C   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  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -3.9637    3.5867    0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    2.3080    0.1271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467    1.7696   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    2.0227   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    1.2946   -1.3900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1034    0.1441   -0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1841   -0.6073   -0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415    0.2422   -1.9810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0684    0.8106   -1.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1314    0.5120   -2.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480   -1.8246   -0.1233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9601   -1.7249    0.2219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9404   -2.5849   -0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3545   -2.4312    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6353   -3.4901   -1.1397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858   -2.0704    1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596   -2.4421    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039   -1.3140    0.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896   -1.4794    0.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -0.5437    0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0858   -0.7051    1.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4140   -1.8762    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4606    0.5899    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4089    1.5920   -0.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1451    1.4904   -1.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786    0.8142   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    1.9755   -1.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4937    3.1664   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2122   -0.1373   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332    4.3667   -0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1309    3.6965    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133    3.7152    1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3051    2.7206    0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361    1.8444   -2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -0.0803   -2.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -2.6733   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2226   -0.9773    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9935   -2.0700   -0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7931   -3.4178    0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4262   -1.7766    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -1.1893    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -2.9150    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -3.2271    0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0304   -2.8791    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0641   -2.3805    1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1534   -2.8043    1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9525   -1.9148    2.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5331   -1.9047    2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1725    1.1032   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6693    0.7925   -2.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274    2.4636   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610    3.6841   -0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    2.8790    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573    3.8566   -0.2438 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  8  1  0
  8  7  1  0
  7  6  2  0
  6 29  1  0
 29 18  2  0
 18 17  1  0
 17 16  1  0
 16 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 27  1  0
 27 28  1  0
  8  9  1  0
  9 10  2  0
  9  3  1  0
  6  5  1  0
 26 29  1  0
 11  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  6
  8 35  1  6
 17 43  1  0
 17 44  1  0
 16 41  1  0
 16 42  1  0
 11 36  1  6
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 19 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
M  END


  Mrv1533004161520152D          

 29 32  0  0  0  0            999 V2000
    4.9272    1.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2091    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951    1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140    2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4194    2.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    2.6522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9033    2.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844    1.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675    1.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678    2.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368    3.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8226    3.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    3.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    4.0737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392    4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1365    5.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    5.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7227    2.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135    1.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039    1.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947    0.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045    0.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952   -0.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4768    1.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0765    0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670    0.7438    0.0000 C   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  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2C(C3=C2C2=C(CCC3NC(C)=O)C=C(OC)C(OC)=C2OC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO6/c1-10(24)23-13-7-6-11-8-15(27-3)21(28-4)22(29-5)16(11)17-12-9-14(26-2)20(25)18(12)19(13)17/h8-9,12-13,18H,6-7H2,1-5H3,(H,23,24)

> <INCHI_KEY>
VKPVZFOUXUQJMW-UHFFFAOYSA-N

> <FORMULA>
C22H25NO6

> <MOLECULAR_WEIGHT>
399.443

> <EXACT_MASS>
399.168187529

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.43518589616275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2(7),3,5,14-pentaen-10-yl}acetamide

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.9016405560000008

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.101000289421716

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.545578632662528

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1507698958788413

> <JCHEM_POLAR_SURFACE_AREA>
83.09

> <JCHEM_REFRACTIVITY>
108.40119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2(7),3,5,14-pentaen-10-yl}acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       9.197   2.374   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.857   1.616   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.530   2.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.118   1.784   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.098   2.938   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.879   4.264   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.383   3.931   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.537   4.951   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.553   5.046   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.771   3.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.246   3.504   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.127   4.561   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.255   6.096   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.536   6.952   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.003   6.485   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.060   7.604   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.620   9.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.121   9.436   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.677  10.199   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.349   4.120   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.705   2.622   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.181   2.181   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.537   0.683   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.586   1.565   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.942   0.066   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.178  -0.991   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.890   2.005   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.009   0.948   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.485   1.388   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    3    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   15                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   11   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
N-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0,.0,]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidate	Generator
beta Lumicolchicine	MeSH
beta-Lumicolchicine	MeSH
gamma-Lumicolchicine	MeSH
Lumicolchicines	MeSH
gamma Lumicolchicine	MeSH
Lumicolchicine	MeSH

Chemical Formula

C₂₂H₂₅NO₆

Average Mass

399.4430 Da

Monoisotopic Mass

399.16819 Da

IUPAC Name

N-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2(7),3,5,14-pentaen-10-yl}acetamide

Traditional Name

N-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2(7),3,5,14-pentaen-10-yl}acetamide

CAS Registry Number

Not Available

SMILES

COC1=CC2C(C3=C2C2=C(CCC3NC(C)=O)C=C(OC)C(OC)=C2OC)C1=O

InChI Identifier

InChI=1S/C22H25NO6/c1-10(24)23-13-7-6-11-8-15(27-3)21(28-4)22(29-5)16(11)17-12-9-14(26-2)20(25)18(12)19(13)17/h8-9,12-13,18H,6-7H2,1-5H3,(H,23,24)

InChI Key

VKPVZFOUXUQJMW-UHFFFAOYSA-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 arenarium	LOTUS Database	35616633
Colchicum autumnale	LOTUS Database	35616633
Colchicum bivonae	LOTUS Database	35616633
Colchicum laetum	LOTUS Database	35616633
Colchicum raddeanum	LOTUS Database	35616633
Colchicum szovitsii	LOTUS Database	35616633
Colchicum turcicum	LOTUS Database	35616633
Gloriosa superba	LOTUS Database	35616633
Merendera robusta	LOTUS Database	35616633
Wurmbea dioica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lumicolchicine alkaloids. These are alkaloids with a structure based on the tetracyclic lumicolchicine skeleton. They can derive from a colchicine precursor where the cycloheptatriene ring is replaced with a bicyclo[3.2.0]Hepta-2,6-diene ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lumicolchicine alkaloids

Sub Class

Not Available

Direct Parent

Lumicolchicine alkaloids

Alternative Parents

Substituents

Lumicolchicine alkaloid skeleton
Anisole
Alkyl aryl ether
Benzenoid
Acetamide
Carboxamide group
Ketone
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	0.92	ALOGPS
logP	0.9	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.4 m³·mol⁻¹	ChemAxon
Polarizability	42.44 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

110937

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid (NP0309403)

MOL for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

3D MOL for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

3D SDF for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

3D-SDF for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

PDB for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

3D PDB for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

SMILES for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

INCHI for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

Structure for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)

3D Structure for NP0309403 (n-{3,4,5,14-tetramethoxy-13-oxotetracyclo[9.5.0.0²,⁷.0¹²,¹⁶]hexadeca-1(11),2,4,6,14-pentaen-10-yl}ethanimidic acid)