NP-MRD: Showing NP-Card for (11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate (NP0143474)

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Record Information

Version

2.0

Created at

2022-09-01 22:14:05 UTC

Updated at

2022-09-01 22:14:06 UTC

NP-MRD ID

NP0143474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate

Description

Lyscamine belongs to the class of organic compounds known as hydroxy-7-aporphines. These are aporphines containing a hydroxyl group at the 7-position. (11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate is found in Cananga odorata. (11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate was first documented in 2001 (PMID: 11374955). Based on a literature review very few articles have been published on Lyscamine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200142D          

 23 27  0  0  1  0            999 V2000
   -1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
   -0.1842    1.8695    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920   -2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -2.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 10 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -3.3094    0.7029    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3161   -0.1946    0.4882 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.6622   -0.7121    1.5510 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9854   -1.3148   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737   -2.2435   -0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6226   -1.9561   -0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3062   -2.9817   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6050   -2.6548   -0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0547   -1.3520   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0786   -0.3434   -0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2484   -0.6507   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    0.3326   -0.4355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9365    1.7208   -0.2337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6000    2.4131    0.7793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981    1.9840   -0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8595    3.2993    0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811    3.6681    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415    2.6779    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8031    1.3326    0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4963    1.0315   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4286   -1.4138   -0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410   -2.7448    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412   -3.4847   -0.4871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2446    0.0895    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465    1.4732    0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507    1.0793    1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6758   -0.8436   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6682   -1.8387    0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191   -2.1808   -2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2750   -3.3035   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577   -3.9851   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8305    0.2280   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1950    2.3141   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7334    3.3726    0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1366    4.1045    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    4.7054    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    2.9738    0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273    0.6599    0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -2.9168    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437   -3.0477   -0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 12  2  1  0
 20 15  1  0
 11  6  1  0
 23  8  1  0
 20 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
 22 39  1  0
 22 40  1  0
 12 32  1  6
 13 33  1  6
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  CHG  2   2   1   3  -1
M  END


  Mrv1652309022200142D          

 23 27  0  0  1  0            999 V2000
   -1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
   -0.1842    1.8695    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920   -2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -2.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 10 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0143474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N@@+]1([O-])CCC2=CC3=C(OCO3)C3=C2[C@@H]1[C@@H](O)C1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO4/c1-19(21)7-6-10-8-13-18(23-9-22-13)15-11-4-2-3-5-12(11)17(20)16(19)14(10)15/h2-5,8,16-17,20H,6-7,9H2,1H3/t16-,17+,19-/m1/s1

> <INCHI_KEY>
PQQSHMZUVWGXSV-ZIFCJYIRSA-N

> <FORMULA>
C18H17NO4

> <MOLECULAR_WEIGHT>
311.337

> <EXACT_MASS>
311.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.44541150157389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11R,12R,13S)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
1.281274165

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.487660832129833

> <JCHEM_PKA_STRONGEST_BASIC>
3.2052571615455467

> <JCHEM_POLAR_SURFACE_AREA>
61.75

> <JCHEM_REFRACTIVITY>
85.04560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11R,12R,13S)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate

> <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      -2.324   3.490   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+1
HETATM    3  O   UNK     0      -0.344   3.490   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.478  -3.340   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.852  -4.747   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.320  -4.586   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   10                                                  
CONECT   21    9   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    8                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₇NO₄

Average Mass

311.3370 Da

Monoisotopic Mass

311.11576 Da

IUPAC Name

(11R,12R,13S)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate

Traditional Name

(11R,12R,13S)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate

CAS Registry Number

Not Available

SMILES

C[N@@+]1([O-])CCC2=CC3=C(OCO3)C3=C2[C@@H]1[C@@H](O)C1=CC=CC=C31

InChI Identifier

InChI=1S/C18H17NO4/c1-19(21)7-6-10-8-13-18(23-9-22-13)15-11-4-2-3-5-12(11)17(20)16(19)14(10)15/h2-5,8,16-17,20H,6-7,9H2,1H3/t16-,17+,19-/m1/s1

InChI Key

PQQSHMZUVWGXSV-ZIFCJYIRSA-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
Cananga odorata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy-7-aporphines. These are aporphines containing a hydroxyl group at the 7-position.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Hydroxy-7-aporphines

Direct Parent

Hydroxy-7-aporphines

Alternative Parents

Substituents

Hydroxy-7-aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Benzenoid
Trialkyl amine oxide
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
N-oxide
Acetal
Organic oxide
Organic salt
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic cation
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	0.4	ALOGPS
logP	1.28	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.49	ChemAxon
pKa (Strongest Basic)	3.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.75 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.05 m³·mol⁻¹	ChemAxon
Polarizability	32.45 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

24717075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584791

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsieh TJ, Chang FR, Chia YC, Chen CY, Chiu HF, Wu YC: Cytotoxic constituents of the fruits of Cananga odorata. J Nat Prod. 2001 May;64(5):616-9. doi: 10.1021/np0005208. [PubMed:11374955 ]
LOTUS database [Link]

Showing NP-Card for (11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate (NP0143474)

MOL for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

3D MOL for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

3D SDF for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

3D-SDF for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

PDB for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

3D PDB for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

SMILES for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

INCHI for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

Structure for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)

3D Structure for NP0143474 ((11r,12r,13s)-13-hydroxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-ium-11-olate)