NP-MRD: Showing NP-Card for n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid (NP0222716)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-06 00:37:16 UTC

Updated at

2022-09-06 00:37:17 UTC

NP-MRD ID

NP0222716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid

Description

5H-Dibenzo[a,c]cycloheptene-2-carboxylic acid, 5-(acetylamino)-6,7-dihydro-3-hydroxy-9,10,11-trimethoxy-, methyl ester, (5S)- belongs to the class of organic compounds known as allocolchicine alkaloids. These are alkaloids with a structure based on the tricyclic allocolchicine skeleton, which consists of a dibenzocycloheptane where the cycloheptane moiety carries the N-acetamide group. n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid is found in Colchicum decaisnei. Based on a literature review very few articles have been published on 5H-Dibenzo[a,c]cycloheptene-2-carboxylic acid, 5-(acetylamino)-6,7-dihydro-3-hydroxy-9,10,11-trimethoxy-, methyl ester, (5S)-.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202372D          

 30 32  0  0  0  0            999 V2000
    6.4486    2.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1472    1.3898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3314    1.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    1.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300    0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128   -0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272   -1.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5444   -0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602   -0.0232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2436   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886   -2.3558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6566   -2.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3016   -2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7795   -1.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -2.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734   -1.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7576   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -0.0232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692    1.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    1.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    1.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9994    1.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878   -0.3921    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
  3  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  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 19 30  1  0  0  0  0
  7 30  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -0.1793    6.7012    0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5326    5.4788    0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1193    4.2816    0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744    4.3341    0.5007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770    2.9538    0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563    1.8397    0.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2126    0.6182    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5728    0.4264   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3524    1.4793   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8122    2.7884   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6921    3.8208   -0.4291 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -0.9423   -0.0659 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5759   -0.8503   -0.4317 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526   -1.9489   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6954   -1.8830   -0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7136   -3.1961   -0.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0073   -1.4166    1.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -2.1785    1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -1.6501    1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5311   -2.5392    1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769   -2.2192    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7926   -3.1578    0.9546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5614   -4.3841    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201   -1.0211    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3032   -0.7871   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7479   -1.1585   -1.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9925   -0.0999   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1883    1.0827   -0.7032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243    1.2916   -2.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805   -0.4473    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    6.5072    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0858    7.3352   -0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670    7.2628    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    1.9590    0.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4160    1.3357   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042    4.7737   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6644   -1.6083   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7777   -1.7177   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -2.8209   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -0.9975   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -4.0066   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.0864    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -0.5354    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758   -3.2778    1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373   -2.1390    2.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3754   -3.5024    1.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7064   -4.8833    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2756   -4.2076    2.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4113   -5.0790    1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7980   -0.2839   -2.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0179   -1.8748   -2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496   -1.6461   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6546    2.3467   -2.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2748    0.6436   -2.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087    1.2861   -2.6263 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 10  5  1  0
 30 19  1  0
 30  7  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  6
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
M  END


  Mrv1652309062202372D          

 30 32  0  0  0  0            999 V2000
    6.4486    2.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1472    1.3898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3314    1.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    1.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300    0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128   -0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272   -1.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5444   -0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602   -0.0232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2436   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886   -2.3558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6566   -2.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3016   -2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7795   -1.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003   -2.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734   -1.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7576   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -0.0232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692    1.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    1.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    1.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9994    1.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878   -0.3921    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
  3  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  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 19 30  1  0  0  0  0
  7 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC2=C(C=C1O)C(CCC1=CC(OC)=C(OC)C(OC)=C21)N=C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO7/c1-11(24)23-16-7-6-12-8-18(27-2)20(28-3)21(29-4)19(12)14-9-15(22(26)30-5)17(25)10-13(14)16/h8-10,16,25H,6-7H2,1-5H3,(H,23,24)

> <INCHI_KEY>
VOKPQOKKNBHZIX-UHFFFAOYSA-N

> <FORMULA>
C22H25NO7

> <MOLECULAR_WEIGHT>
415.442

> <EXACT_MASS>
415.163102149

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.16147890721576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0^{2,7}]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid

> <JCHEM_LOGP>
3.8058124306666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.397277813013265

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.3371888014849755

> <JCHEM_PKA_STRONGEST_BASIC>
2.930093849769479

> <JCHEM_POLAR_SURFACE_AREA>
106.81000000000002

> <JCHEM_REFRACTIVITY>
110.60969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0^{2,7}]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      12.037   4.028   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.475   2.594   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.952   2.365   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.992   3.569   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.389   0.931   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.867   0.702   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.304  -0.732   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.264  -1.936   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.787  -1.706   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.350  -0.273   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.872  -0.043   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.921  -3.437   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       9.125  -4.398   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      10.559  -3.835   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.763  -4.795   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.788  -2.312   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.534  -4.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.146  -3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.804  -1.936   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.281  -1.706   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.718  -0.273   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.196  -0.043   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.235  -1.247   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.678   0.931   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.116   2.365   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.076   3.569   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.201   0.702   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.161   1.906   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.599   3.339   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.764  -0.732   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   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   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   19    7                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅NO₇

Average Mass

415.4420 Da

Monoisotopic Mass

415.16310 Da

IUPAC Name

N-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0^{2,7}]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid

Traditional Name

N-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0^{2,7}]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=C(C=C1O)C(CCC1=CC(OC)=C(OC)C(OC)=C21)N=C(C)O

InChI Identifier

InChI=1S/C22H25NO7/c1-11(24)23-16-7-6-12-8-18(27-2)20(28-3)21(29-4)19(12)14-9-15(22(26)30-5)17(25)10-13(14)16/h8-10,16,25H,6-7H2,1-5H3,(H,23,24)

InChI Key

VOKPQOKKNBHZIX-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 decaisnei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as allocolchicine alkaloids. These are alkaloids with a structure based on the tricyclic allocolchicine skeleton, which consists of a dibenzocycloheptane where the cycloheptane moiety carries the N-acetamide group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Allocolchicine alkaloids

Sub Class

Not Available

Direct Parent

Allocolchicine alkaloids

Alternative Parents

Substituents

Allocolchicine alkaloid skeleton
Salicylic acid or derivatives
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Methyl ester
Acetamide
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	3.81	ChemAxon
pKa (Strongest Acidic)	5.34	ChemAxon
pKa (Strongest Basic)	2.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.81 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	110.61 m³·mol⁻¹	ChemAxon
Polarizability	43.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

550737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

634450

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid (NP0222716)

MOL for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

3D MOL for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

3D SDF for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

3D-SDF for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

PDB for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

3D PDB for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

SMILES for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

INCHI for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

Structure for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)

3D Structure for NP0222716 (n-[5-hydroxy-13,14,15-trimethoxy-4-(methoxycarbonyl)tricyclo[9.4.0.0²,⁷]pentadeca-1(15),2(7),3,5,11,13-hexaen-8-yl]ethanimidic acid)