NP-MRD: Showing NP-Card for (12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol (NP0325172)

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Record Information

Version

2.0

Created at

2022-09-12 05:43:20 UTC

Updated at

2022-09-12 05:43:21 UTC

NP-MRD ID

NP0325172

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol

Description

Cassythicine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. (12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol is found in Beilschmiedia kunstleri, Cassytha filiformis, Illigera luzonensis, Licaria triandra, Litsea lancifolia, Litsea sericea, Neolitsea parvigemma, Stephania pierrei and Stephania tetrandra. (12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol was first documented in 2011 (PMID: 21818061). Based on a literature review a small amount of articles have been published on Cassythicine (PMID: 21490559) (PMID: 33635585) (PMID: 32048433) (PMID: 22481540).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207432D          

 24 28  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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  1  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  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
    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
    2.0420    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    2.0445    0.0000 O   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  5 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  6  0  0  0
 23 24  1  0  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
    4.9081    0.3389    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894    0.1736   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4387    0.0225   -0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    0.0326    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253   -0.1127   -0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -0.2691   -1.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9915   -0.2802   -2.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2551   -0.1356   -2.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3776   -0.1480   -2.9237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -0.3778   -2.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563   -0.6444   -1.4150 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3316   -0.3595    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4688   -0.3558    0.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -0.1376    2.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    0.0673    2.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121    0.0662    1.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -0.1514    0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454    0.3007    2.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518    0.1881    4.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564    0.2982    4.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8283   -0.5689    0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665   -0.8436   -1.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457   -0.0880   -1.8255 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    1.3220   -1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9442    0.5573    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005    1.1426    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5597   -0.5894    1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4587    0.1543    1.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8401   -0.4055   -3.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2744   -0.0362   -2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835   -1.2358   -3.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395    0.5737   -2.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -1.7712   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789   -0.1343    2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2047    1.0284    4.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0844   -0.7861    4.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2272   -1.4866    0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303    0.2447    0.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8508   -0.5517   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6601   -1.9197   -1.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    1.8235   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9396    1.6509   -1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6869    1.6510   -0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 10  1  0
 10 11  1  0
 11 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 21 13  1  0
 13 12  1  0
 12 17  2  0
 17 16  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 15  1  0
 15 14  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
 17  5  1  0
 15 16  2  0
 12 11  1  0
 14 13  2  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 24 41  1  0
 24 42  1  0
 24 43  1  0
 22 39  1  0
 22 40  1  0
 21 37  1  0
 21 38  1  0
 19 35  1  0
 19 36  1  0
 14 34  1  0
  7 29  1  0
  9 30  1  0
M  END


  Mrv1652309122207432D          

 24 28  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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  1  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  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
    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
    2.0420    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    2.0445    0.0000 O   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  5 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  6  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325172

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C[C@@H]3N(C)CCC4=C3C2=C2OCOC2=C4)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO4/c1-20-4-3-10-7-16-19(24-9-23-16)18-12-8-15(22-2)14(21)6-11(12)5-13(20)17(10)18/h6-8,13,21H,3-5,9H2,1-2H3/t13-/m0/s1

> <INCHI_KEY>
MPWZJVCAMFAIGV-ZDUSSCGKSA-N

> <FORMULA>
C19H19NO4

> <MOLECULAR_WEIGHT>
325.364

> <EXACT_MASS>
325.131408096

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.45378931591111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S)-17-methoxy-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(19),15,17-hexaen-16-ol

> <JCHEM_LOGP>
2.863408908

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.700159362262797

> <JCHEM_PKA_STRONGEST_BASIC>
6.984156315510627

> <JCHEM_POLAR_SURFACE_AREA>
51.16000000000001

> <JCHEM_REFRACTIVITY>
90.2373

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-17-methoxy-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(19),15,17-hexaen-16-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.812   2.570   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.185   3.977   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.654   3.816   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12    5                                                  
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   13   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   11   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
N-Methyl-actinodaphnine	MeSH
N-Methylactinodaphnine	MeSH

Chemical Formula

C₁₉H₁₉NO₄

Average Mass

325.3640 Da

Monoisotopic Mass

325.13141 Da

IUPAC Name

(12S)-17-methoxy-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(19),15,17-hexaen-16-ol

Traditional Name

(12S)-17-methoxy-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(19),15,17-hexaen-16-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C[C@@H]3N(C)CCC4=C3C2=C2OCOC2=C4)C=C1O

InChI Identifier

InChI=1S/C19H19NO4/c1-20-4-3-10-7-16-19(24-9-23-16)18-12-8-15(22-2)14(21)6-11(12)5-13(20)17(10)18/h6-8,13,21H,3-5,9H2,1-2H3/t13-/m0/s1

InChI Key

MPWZJVCAMFAIGV-ZDUSSCGKSA-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
Beilschmiedia kunstleri	LOTUS Database	35616633
Cassytha filiformis	LOTUS Database	35616633
Illigera luzonensis	LOTUS Database	35616633
Licaria triandra	LOTUS Database	35616633
Litsea lancifolia	LOTUS Database	35616633
Litsea sericea	LOTUS Database	35616633
Neolitsea parvigemma	LOTUS Database	35616633
Stephania pierrei	LOTUS Database	35616633
Stephania tetrandra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Anisole
Aralkylamine
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Oxacycle
Azacycle
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:17 )
Isoquinoline alkaloids (C09389 )

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	2.86	ChemAxon
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	6.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.24 m³·mol⁻¹	ChemAxon
Polarizability	35.45 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

C00001834

Chemspider ID

390701

KEGG Compound ID

C09389

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442194

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1835101

References

General References

Mollataghi A, Hadi AH, Awang K, Mohamad J, Litaudon M, Mukhtar MR: (+)-Kunstlerone, a new antioxidant neolignan from the Leaves of Beilschmiedia kunstleri gamble. Molecules. 2011 Aug 4;16(8):6582-90. doi: 10.3390/molecules16086582. [PubMed:21818061 ]
Sulaiman SN, Mukhtar MR, Hadi AH, Awang K, Hazni H, Zahari A, Litaudon M, Zaima K, Morita H: Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia. Molecules. 2011 Apr 13;16(4):3119-27. doi: 10.3390/molecules16043119. [PubMed:21490559 ]
Barbosa H, Costa-Silva TA, Alves Conserva GA, Araujo AJ, Lordello ALL, Antar GM, Amaral M, Soares MG, Tempone AG, Lago JHG: Aporphine Alkaloids from Ocotea puberula with Anti-Trypanosoma Cruzi Potential - Activity of Dicentrine-beta-N-Oxide in the Plasma Membrane Electric Potentials. Chem Biodivers. 2021 Apr;18(4):e2001022. doi: 10.1002/cbdv.202001022. Epub 2021 Mar 1. [PubMed:33635585 ]
Cavallaro V, Murray AP, Pungitore CR, Gutierrez LJ: Aporphinoid Alkaloids Derivatives as Selective Cholinesterases Inhibitors: Biological Evaluation and Docking Study. Mol Inform. 2020 Nov;39(11):e1900125. doi: 10.1002/minf.201900125. Epub 2020 Feb 21. [PubMed:32048433 ]
Mollataghi A, Hadi AH, Cheah SC: (-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of Beilschmiedia kunstleri gamble. Molecules. 2012 Apr 5;17(4):4197-208. doi: 10.3390/molecules17044197. [PubMed:22481540 ]
LOTUS database [Link]

Showing NP-Card for (12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol (NP0325172)

MOL for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

3D MOL for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

3D SDF for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

3D-SDF for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

PDB for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

3D PDB for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

SMILES for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

INCHI for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

Structure for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)

3D Structure for NP0325172 ((12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaen-16-ol)