NP-MRD: Showing NP-Card for methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate (NP0183356)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 22:14:44 UTC

Updated at

2022-09-03 22:14:44 UTC

NP-MRD ID

NP0183356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate

Description

Lanceomagine belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate is found in Hunteria zeylanica. Based on a literature review very few articles have been published on lanceomagine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200142D          

 28 33  0  0  1  0            999 V2000
   -1.2052    2.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615    1.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -0.1014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5887    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403    0.6878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9344    0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3237   -0.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5835    0.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942    1.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3696    1.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441    2.0386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384    2.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442    1.8900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5745    1.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    0.1265    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5311   -0.5006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106   -0.2685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0696    0.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2409    1.2987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6290    1.4764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3102    2.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5081    2.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099    2.8938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    3.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  6  0  0  0
 23 22  1  1  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
    1.5556   -3.4237    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1886   -2.1696    1.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2409   -1.0539    1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9563    0.1260    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5754    1.3399    1.0275 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.9372    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497    1.0868    1.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    0.9388    0.1256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3710    1.3484   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442    2.2823    0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4130    2.6620   -0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9669    2.1076   -1.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2333    1.1798   -1.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804    0.8173   -1.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180   -0.1230   -2.2228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588   -0.9213   -3.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928   -0.1367   -1.8910 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6936    1.1507   -2.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9455    1.6940   -0.7819 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6746    3.0387   -0.7419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609    1.3477   -0.3669 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6186   -0.0091   -0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6560   -0.9512   -0.2213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2671   -0.4624   -0.3829 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8002   -1.3614    0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657   -2.0010   -0.7284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0374   -1.5686    1.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591   -2.4305    1.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -4.2523    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -3.5462    0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -3.6765    1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6676   -2.1307    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -0.0359    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798    0.1815    2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687    1.8589    2.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308    2.9997    1.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3696    0.1065    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820    1.5750    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678    2.7790    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9839    3.4077    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9540    2.3748   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6174    0.7073   -2.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9257   -0.3893   -4.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026   -1.1861   -2.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667   -1.8527   -3.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -0.8979   -2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933    3.5714   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0249    2.1343   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3956    0.0481   -2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605   -0.3415   -0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258   -1.8941   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -1.9659    1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573   -2.6292    2.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -3.3908    1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 25  1  0
 25 26  2  0
 24 25  1  1
 24 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
  3  2  2  0
  2  1  1  0
 23 24  1  0
 14  9  1  0
  8 24  1  0
 15 17  1  0
  8 19  1  0
  5 21  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 17 46  1  6
 20 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 23 51  1  6
  4 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309042200142D          

 28 33  0  0  1  0            999 V2000
   -1.2052    2.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615    1.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -0.1014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5887    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403    0.6878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9344    0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3237   -0.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5835    0.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942    1.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3696    1.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441    2.0386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384    2.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442    1.8900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5745    1.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    0.1265    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5311   -0.5006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106   -0.2685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0696    0.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2409    1.2987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6290    1.4764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3102    2.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5081    2.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099    2.8938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    3.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  6  0  0  0
 23 22  1  1  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12[C@@H]3O[C@]4(O)[C@@H]5C[C@H]1\C(CN5CC[C@]24C1=CC=CC=C1N3C)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O4/c1-4-13-12-24-10-9-20-14-7-5-6-8-16(14)23(2)18-21(20,19(25)27-3)15(13)11-17(24)22(20,26)28-18/h4-8,15,17-18,26H,9-12H2,1-3H3/b13-4-/t15-,17-,18-,20-,21+,22+/m0/s1

> <INCHI_KEY>
YWHJXIKKMXPHRE-MNJCRSHWSA-N

> <FORMULA>
C22H26N2O4

> <MOLECULAR_WEIGHT>
382.46

> <EXACT_MASS>
382.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.81423117526542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,6E,7S,9S,10S,12S,20R)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0^{1,10}.0^{4,9}.0^{7,20}.0^{14,19}]icosa-14,16,18-triene-20-carboxylate

> <JCHEM_LOGP>
2.4914813406666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.984980597894461

> <JCHEM_PKA_STRONGEST_BASIC>
7.641039672502858

> <JCHEM_POLAR_SURFACE_AREA>
62.239999999999995

> <JCHEM_REFRACTIVITY>
104.6986

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,6E,7S,9S,10S,12S,20R)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0^{1,10}.0^{4,9}.0^{7,20}.0^{14,19}]icosa-14,16,18-triene-20-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.250   5.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.915   3.682   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.045   2.412   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.628   0.939   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.353  -0.189   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.099   1.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.478   1.989   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.942   1.284   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.611   1.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.338  -0.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.877  -0.387   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.689   0.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.963   2.279   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.423   2.329   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.816   3.805   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       4.552   5.158   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.322   3.528   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.939   1.900   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.857   0.236   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.858  -0.934   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.206  -0.501   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.130   0.740   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.450   2.424   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.174   2.756   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.579   4.176   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.948   4.371   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.512   5.402   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.917   6.822   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   24                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18    8   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23   17    8   25                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₂O₄

Average Mass

382.4600 Da

Monoisotopic Mass

382.18926 Da

IUPAC Name

methyl (1S,6E,7S,9S,10S,12S,20R)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0^{1,10}.0^{4,9}.0^{7,20}.0^{14,19}]icosa-14,16,18-triene-20-carboxylate

Traditional Name

methyl (1S,6E,7S,9S,10S,12S,20R)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0^{1,10}.0^{4,9}.0^{7,20}.0^{14,19}]icosa-14,16,18-triene-20-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12[C@@H]3O[C@]4(O)[C@@H]5C[C@H]1\C(CN5CC[C@]24C1=CC=CC=C1N3C)=C/C

InChI Identifier

InChI=1S/C22H26N2O4/c1-4-13-12-24-10-9-20-14-7-5-6-8-16(14)23(2)18-21(20,19(25)27-3)15(13)11-17(24)22(20,26)28-18/h4-8,15,17-18,26H,9-12H2,1-3H3/b13-4-/t15-,17-,18-,20-,21+,22+/m0/s1

InChI Key

YWHJXIKKMXPHRE-MNJCRSHWSA-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
Hunteria zeylanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Benzoxazepine
Tetrahydroquinoline
Quinolizidine
Dialkylarylamine
Meta-oxazepine
Oxepane
Aralkylamine
Piperidine
Benzenoid
Methyl ester
Tetrahydrofuran
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Hemiacetal
Oxacycle
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	2.49	ChemAxon
pKa (Strongest Acidic)	10.98	ChemAxon
pKa (Strongest Basic)	7.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.24 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.7 m³·mol⁻¹	ChemAxon
Polarizability	39.81 Å³	ChemAxon
Number of Rings	6	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

24689312

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584235

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate (NP0183356)

MOL for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

3D MOL for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

3D SDF for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

3D-SDF for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

PDB for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

3D PDB for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

SMILES for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

INCHI for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

Structure for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)

3D Structure for NP0183356 (methyl (1s,6e,7s,9s,10s,12s,20r)-6-ethylidene-10-hydroxy-13-methyl-11-oxa-4,13-diazahexacyclo[10.7.1.0¹,¹⁰.0⁴,⁹.0⁷,²⁰.0¹⁴,¹⁹]icosa-14,16,18-triene-20-carboxylate)