NP-MRD: Showing NP-Card for (1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol (NP0144456)

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Record Information

Version

2.0

Created at

2022-09-01 23:26:04 UTC

Updated at

2022-09-01 23:26:04 UTC

NP-MRD ID

NP0144456

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol

Description

DRUPACINE belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group. (1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol is found in Cephalotaxus harringtonia. (1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol was first documented in 2003 (PMID: 15040085). Based on a literature review a small amount of articles have been published on DRUPACINE (PMID: 19393155) (PMID: 23785026) (PMID: 17705540) (PMID: 15491099).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022201262D          

 24 29  0  0  1  0            999 V2000
    3.7806   -1.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -0.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    0.2707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3631    0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612    0.8689    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6843    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847    1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    2.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707    1.7188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437    2.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4964    2.0613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2707    1.2149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3239    1.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0681    2.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7485    1.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    1.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9404    0.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600    1.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162    0.6864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9063   -0.0637    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5082   -0.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472    0.7102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9823    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5505    2.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  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
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 19 18  1  1  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
M  END

     RDKit          3D

 45 50  0  0  0  0  0  0  0  0999 V2000
   -2.3787    3.4545    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810    2.1359    0.0368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    1.2472   -0.0029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3019   -0.1239    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250   -0.9416    0.5492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6187   -2.0894    1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1601   -3.0197    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -2.7287   -0.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5541   -1.5490   -0.5912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983   -0.7636   -1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799    0.6390   -1.6185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9804    1.5140   -1.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    0.4535   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3185    0.6333   -1.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840    0.4870   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4120    0.1539    0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1803   -0.0224    1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    0.1250    0.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354   -0.0901    1.3977 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9276    1.2861    1.3121 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0294    2.2899    1.2935 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6891    0.0568    1.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622    0.0068    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8363    0.5941   -0.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7580    3.7409    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159    3.6733   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3015    4.0687    0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9959   -0.0664    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208   -0.4790   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695   -1.6915    2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505   -2.5714    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -4.0902    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2510   -2.7595    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -3.5812   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926   -2.5451   -1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600   -0.7575   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271   -1.2673   -2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133    1.0049   -2.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3626    0.8901   -2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987   -0.2854    2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851   -0.4187    2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254    1.3392    2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    2.5498    0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989   -1.0679    0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5068    0.5654    0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 12  3  1  0
 18 13  1  0
 20  3  1  0
  9  5  1  0
 24 15  1  0
 19  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 14 39  1  0
 23 44  1  0
 23 45  1  0
 17 40  1  0
 19 41  1  1
 20 42  1  1
 21 43  1  0
M  END


  Mrv1652309022201262D          

 24 29  0  0  1  0            999 V2000
    3.7806   -1.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -0.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    0.2707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3631    0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612    0.8689    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6843    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847    1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    2.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707    1.7188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437    2.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4964    2.0613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2707    1.2149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3239    1.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0681    2.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7485    1.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    1.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9404    0.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600    1.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162    0.6864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9063   -0.0637    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5082   -0.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472    0.7102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9823    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5505    2.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  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
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 19 18  1  1  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12C[C@@]34CCCN3C[C@@H](O1)C1=CC3=C(OCO3)C=C1[C@H]4[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO5/c1-21-18-8-17-3-2-4-19(17)7-14(24-18)10-5-12-13(23-9-22-12)6-11(10)15(17)16(18)20/h5-6,14-16,20H,2-4,7-9H2,1H3/t14-,15+,16-,17-,18+/m1/s1

> <INCHI_KEY>
KYTDBKDWDOVRLJ-ILOCAZANSA-N

> <FORMULA>
C18H21NO5

> <MOLECULAR_WEIGHT>
331.368

> <EXACT_MASS>
331.14197278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.29076709196367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,11R,12R,13S,15R)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0^{2,10}.0^{4,8}.0^{11,15}.0^{15,19}]henicosa-2,4(8),9-trien-12-ol

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
1.449970142

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.866454932727176

> <JCHEM_PKA_STRONGEST_BASIC>
9.047375943057624

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
83.86590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11R,12R,13S,15R)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0^{2,10}.0^{4,8}.0^{11,15}.0^{15,19}]henicosa-2,4(8),9-trien-12-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       7.057  -1.887   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.776  -1.031   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.877   0.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.411   0.076   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.781   1.622   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.144   1.532   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.025   2.656   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.828   3.977   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.239   3.208   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.122   4.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.527   3.848   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.105   2.268   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.071   3.655   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.461   4.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.731   3.449   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.611   1.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.222   1.249   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.952   2.120   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.564   1.281   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.292  -0.119   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.415  -1.172   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.035   1.326   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.034   2.498   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.228   3.810   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12   20                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    9   19                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    3                                                       
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    5   20                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₁NO₅

Average Mass

331.3680 Da

Monoisotopic Mass

331.14197 Da

IUPAC Name

(1S,11R,12R,13S,15R)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0^{2,10}.0^{4,8}.0^{11,15}.0^{15,19}]henicosa-2,4(8),9-trien-12-ol

Traditional Name

(1S,11R,12R,13S,15R)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0^{2,10}.0^{4,8}.0^{11,15}.0^{15,19}]henicosa-2,4(8),9-trien-12-ol

CAS Registry Number

Not Available

SMILES

CO[C@@]12C[C@@]34CCCN3C[C@@H](O1)C1=CC3=C(OCO3)C=C1[C@H]4[C@H]2O

InChI Identifier

InChI=1S/C18H21NO5/c1-21-18-8-17-3-2-4-19(17)7-14(24-18)10-5-12-13(23-9-22-12)6-11(10)15(17)16(18)20/h5-6,14-16,20H,2-4,7-9H2,1H3/t14-,15+,16-,17-,18+/m1/s1

InChI Key

KYTDBKDWDOVRLJ-ILOCAZANSA-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
Cephalotaxus harringtonia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cephalotaxus alkaloids

Sub Class

Not Available

Direct Parent

Cephalotaxus alkaloids

Alternative Parents

Substituents

Cephalotaxine
Cephalotaxus alkaloid skeleton
Benzazepine
Benzodioxole
Ketal
Aralkylamine
Azepine
Para-oxazepine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.8	ALOGPS
logP	1.45	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	9.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.87 m³·mol⁻¹	ChemAxon
Polarizability	34.29 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

C00027347

Chemspider ID

82964698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133645824

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Z, Du Q, Wang K, Xiu L, Song G: Completed preparative separation of alkaloids from Cephaltaxus fortunine by step-pH-gradient high-speed counter-current chromatography. J Chromatogr A. 2009 May 29;1216(22):4663-7. doi: 10.1016/j.chroma.2009.03.083. Epub 2009 Apr 7. [PubMed:19393155 ]
Wen Y, Meyer SL, Masler EP, Zhang F, Liao J, Wei X, Chitwood DJ: Nematotoxicity of drupacine and a Cephalotaxus alkaloid preparation against the plant-parasitic nematodes Meloidogyne incognita and Bursaphelenchus xylophilus. Pest Manag Sci. 2013 Sep;69(9):1026-33. doi: 10.1002/ps.3548. Epub 2013 Jun 20. [PubMed:23785026 ]
Liu Q, Ferreira EM, Stoltz BM: Convergency and divergency as strategic elements in total synthesis: the total synthesis of (-)-drupacine and the formal total synthesis of (+/-)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine. J Org Chem. 2007 Sep 14;72(19):7352-8. doi: 10.1021/jo0710883. Epub 2007 Aug 18. [PubMed:17705540 ]
Ye XR, Chai YH, Li XN, Wu KM: [Studies on the synthesis and antitumor activity of the derivatives of cephalotaxine alkaloid esters]. Yao Xue Xue Bao. 2004 Jun;39(6):429-33. [PubMed:15491099 ]
Ye XR, Wu KM: [Synthesis and antitumor activity of the derivatives of cephalotaxine and drupacine]. Yao Xue Xue Bao. 2003 Dec;38(12):919-23. [PubMed:15040085 ]
LOTUS database [Link]

Showing NP-Card for (1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol (NP0144456)

MOL for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

3D MOL for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

3D SDF for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

3D-SDF for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

PDB for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

3D PDB for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

SMILES for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

INCHI for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

Structure for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)

3D Structure for NP0144456 ((1s,11r,12r,13s,15r)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.0²,¹⁰.0⁴,⁸.0¹¹,¹⁵.0¹⁵,¹⁹]henicosa-2,4(8),9-trien-12-ol)