NP-MRD: Showing NP-Card for 17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate (NP0280189)

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Record Information

Version

2.0

Created at

2022-09-09 05:50:09 UTC

Updated at

2022-09-09 05:50:09 UTC

NP-MRD ID

NP0280189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate

Description

18-(Acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]Nonadeca-2,4(8),9-trien-17-yl acetate belongs to the class of organic compounds known as lycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the lycorine skeleton, made up of a pyrrolo[d,e]phenanthridine ring system. 17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate is found in Crinum kirkii, Cyrtanthus elatus and Narcissus tazetta. 18-(Acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]Nonadeca-2,4(8),9-trien-17-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501372D          

 27 31  0  0  0  0            999 V2000
   -0.3352   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -2.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7768   -2.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209   -2.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2629    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902   -1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748   -1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.8491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -2.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    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
  2  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 21 27  1  0  0  0  0
  7 27  1  0  0  0  0
 10 27  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    2.8417    3.1127   -2.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    2.0132   -1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1175    1.9468   -1.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    1.0685   -1.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947   -0.0161   -0.5866 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1940   -1.2865   -1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -2.0164   -1.3627 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4840   -2.6149   -2.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419   -2.6832   -2.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615   -1.6052   -1.5705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -1.9680   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4531   -0.7037    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7242   -0.2548    0.5792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    0.9342    1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7841    1.6511    1.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5309    1.1493    1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275    0.0009    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798   -0.6185    0.3080 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1893    0.0539    0.5480 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8135   -0.3798    1.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1076    0.4246    2.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7566   -0.1640    4.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375    1.6272    2.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1769   -0.9269   -1.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2541    2.7698    2.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    2.9191    2.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0527    1.6054    1.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7890    3.4515   -3.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    2.8704   -3.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4755    3.9895   -2.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.0766   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9712   -2.0089   -0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831   -1.1069   -2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -2.7246   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -3.6106   -2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -1.8750   -3.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -2.6403   -3.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3219   -3.6398   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7155   -2.7240    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1878   -2.3404   -0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112   -0.8043    0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834    1.7002    1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0413   -1.6159    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0279    1.1443    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -1.2090    4.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8640   -0.1154    3.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4762    0.4162    4.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0548   -0.0294   -1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8345    3.5885    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282    3.1687    3.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 25  1  0
 25 26  1  0
 26 27  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 24  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19  5  1  0
 24  7  1  0
 24 10  1  0
 17 12  1  0
 27 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  1
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 26 49  1  0
 26 50  1  0
 16 42  1  0
 18 43  1  1
 24 48  1  6
 19 44  1  1
 22 45  1  0
 22 46  1  0
 22 47  1  0
M  END


  Mrv1533004241501372D          

 27 31  0  0  0  0            999 V2000
   -0.3352   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -2.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7768   -2.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209   -2.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2629    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902   -1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748   -1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.8491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -2.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    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
  2  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 21 27  1  0  0  0  0
  7 27  1  0  0  0  0
 10 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2CCN3CC4=CC5=C(OCO5)C=C4C(C23)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO6/c1-10(22)26-17-5-12-3-4-21-8-13-6-15-16(25-9-24-15)7-14(13)18(19(12)21)20(17)27-11(2)23/h6-7,12,17-20H,3-5,8-9H2,1-2H3

> <INCHI_KEY>
IUKYXZADSGGCJJ-UHFFFAOYSA-N

> <FORMULA>
C20H23NO6

> <MOLECULAR_WEIGHT>
373.405

> <EXACT_MASS>
373.152537465

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.920398487399794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.2163029223333333

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.145327488212738

> <JCHEM_POLAR_SURFACE_AREA>
74.30000000000001

> <JCHEM_REFRACTIVITY>
93.8656

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.626  -6.501   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.306  -4.995   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.450  -3.964   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.159  -4.519   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.120   1.540   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.919   2.016   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.824   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.919  -0.476   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.264  -1.030   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.088  -3.567   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.553  -3.091   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.873  -1.585   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.697  -4.122   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   12   21                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   21    7   10                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
18-(Acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0,.0,.0,]nonadeca-2,4(8),9-trien-17-yl acetic acid	Generator
Dihydrolycorine acetic acid	Generator

Chemical Formula

C₂₀H₂₃NO₆

Average Mass

373.4050 Da

Monoisotopic Mass

373.15254 Da

IUPAC Name

17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate

Traditional Name

17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2CCN3CC4=CC5=C(OCO5)C=C4C(C23)C1OC(C)=O

InChI Identifier

InChI=1S/C20H23NO6/c1-10(22)26-17-5-12-3-4-21-8-13-6-15-16(25-9-24-15)7-14(13)18(19(12)21)20(17)27-11(2)23/h6-7,12,17-20H,3-5,8-9H2,1-2H3

InChI Key

IUKYXZADSGGCJJ-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
Crinum kirkii	LOTUS Database	35616633
Cyrtanthus elatus	LOTUS Database	35616633
Narcissus tazetta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the lycorine skeleton, made up of a pyrrolo[d,e]phenanthridine ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Lycorine-type amaryllidaceae alkaloids

Direct Parent

Lycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Lycorine skeleton
Benzoquinoline
Phenanthridine
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Dicarboxylic acid or derivatives
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen 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	1.49	ALOGPS
logP	1.22	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.87 m³·mol⁻¹	ChemAxon
Polarizability	38.92 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

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

540777

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate (NP0280189)

MOL for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

3D MOL for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

3D SDF for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

3D-SDF for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

PDB for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

3D PDB for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

SMILES for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

INCHI for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

Structure for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)

3D Structure for NP0280189 (17-(acetyloxy)-5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9-trien-18-yl acetate)