NP-MRD: Showing NP-Card for (12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene (NP0265323)

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Record Information

Version

2.0

Created at

2022-09-08 09:15:43 UTC

Updated at

2022-09-08 09:15:44 UTC

NP-MRD ID

NP0265323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene

Description

Crebanine 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)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene is found in Fissistigma oldhamii, Stephania abyssinica, Stephania cephalantha, Stephania venosa and Xylopia aethiopica. (12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene was first documented in 2017 (PMID: 28703314). Based on a literature review a small amount of articles have been published on Crebanine (PMID: 34684698) (PMID: 30068871) (PMID: 29577069) (PMID: 29386467).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211152D          

 25 29  0  0  1  0            999 V2000
    5.0013   -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
    3.5724   -1.2375    0.0000 C   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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   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
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
  6 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  6  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
    5.4442    1.4822   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452    0.3838   -0.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2703    0.5440   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000    1.7572   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189    1.9731   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301    0.9267   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -0.3262    0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -0.4766   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268   -1.7082    0.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -2.0553    1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -1.5046    0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -1.3413    0.5523 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6786   -0.0080    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0565    0.1201    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6988    1.2983    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9145    2.3879   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430    2.2799   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9139    1.0779   -0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    3.5177   -0.8649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250    4.4811   -0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764    3.6774   -0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7926   -1.1020    0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891   -2.2372   -0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608   -2.3357   -0.1930 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -3.6675   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442    1.9562   -1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841    2.3029   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4768    1.2004   -1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012    2.6035   -1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229    2.9415   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866   -2.8490    1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5373   -2.3756    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -1.1701    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5186   -2.3032   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7533   -1.9374    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332   -1.5019    1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635    1.4001    0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1001    5.2322   -1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9599    4.9360    0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8906   -1.0014    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6676   -1.3396    1.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462   -2.0177   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149   -3.2105    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -3.9032   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076   -3.6792    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385   -4.4286    0.1132 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  7  1  0
  7 11  1  0
 11 12  1  0
 12 24  1  0
 24 25  1  0
 24 23  1  0
 23 22  1  0
 22 14  1  0
 14 13  1  0
 13 18  2  0
 18 17  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 16  1  0
 16 15  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8  3  1  0
 18  6  1  0
 16 17  2  0
 13 12  1  0
 15 14  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  1
 25 44  1  0
 25 45  1  0
 25 46  1  0
 23 42  1  0
 23 43  1  0
 22 40  1  0
 22 41  1  0
 20 38  1  0
 20 39  1  0
 15 37  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
M  END


  Mrv1652309082211152D          

 25 29  0  0  1  0            999 V2000
    5.0013   -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
    3.5724   -1.2375    0.0000 C   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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   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
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
  6 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  6  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(C[C@@H]3N(C)CCC4=C3C2=C2OCOC2=C4)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO4/c1-21-7-6-11-8-16-20(25-10-24-16)18-12-4-5-15(22-2)19(23-3)13(12)9-14(21)17(11)18/h4-5,8,14H,6-7,9-10H2,1-3H3/t14-/m0/s1

> <INCHI_KEY>
UVDQDNQWGQFIAO-AWEZNQCLSA-N

> <FORMULA>
C20H21NO4

> <MOLECULAR_WEIGHT>
339.391

> <EXACT_MASS>
339.14705816

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.20699780549671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1,6,8(20),14,16,18-hexaene

> <JCHEM_LOGP>
3.0093029640000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
6.82709530177039

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
94.71960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1,6,8(20),14,16,18-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.812   2.570   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.185   3.977   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.654   3.816   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   25  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                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13    6                                                  
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   14   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   12   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₁NO₄

Average Mass

339.3910 Da

Monoisotopic Mass

339.14706 Da

IUPAC Name

(12S)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1,6,8(20),14,16,18-hexaene

Traditional Name

(12S)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1,6,8(20),14,16,18-hexaene

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(C[C@@H]3N(C)CCC4=C3C2=C2OCOC2=C4)=C1OC

InChI Identifier

InChI=1S/C20H21NO4/c1-21-7-6-11-8-16-20(25-10-24-16)18-12-4-5-15(22-2)19(23-3)13(12)9-14(21)17(11)18/h4-5,8,14H,6-7,9-10H2,1-3H3/t14-/m0/s1

InChI Key

UVDQDNQWGQFIAO-AWEZNQCLSA-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
Fissistigma oldhamii	LOTUS Database	35616633
Stephania abyssinica	LOTUS Database	35616633
Stephania cephalantha	LOTUS Database	35616633
Stephania venosa	LOTUS Database	35616633
Xylopia aethiopica	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
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organooxygen compound
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	3.01	ChemAxon
pKa (Strongest Basic)	6.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.72 m³·mol⁻¹	ChemAxon
Polarizability	37.21 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

C00025235

Chemspider ID

8218370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10042806

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Le PM, Srivastava V, Nguyen TT, Pradines B, Madamet M, Mosnier J, Trinh TT, Lee H: Stephanine from Stephania venosa (Blume) Spreng Showed Effective Antiplasmodial and Anticancer Activities, the Latter by Inducing Apoptosis through the Reverse of Mitotic Exit. Phytother Res. 2017 Sep;31(9):1357-1368. doi: 10.1002/ptr.5861. Epub 2017 Jul 13. [PubMed:28703314 ]
Wang FX, Zhu N, Zhou F, Lin DX: Natural Aporphine Alkaloids with Potential to Impact Metabolic Syndrome. Molecules. 2021 Oct 10;26(20). pii: molecules26206117. doi: 10.3390/molecules26206117. [PubMed:34684698 ]
Yodkeeree S, Ooppachai C, Pompimon W, Limtrakul Dejkriengkraikul P: O-Methylbulbocapnine and Dicentrine Suppress LPS-Induced Inflammatory Response by Blocking NF-kappaB and AP-1 Activation through Inhibiting MAPKs and Akt Signaling in RAW264.7 Macrophages. Biol Pharm Bull. 2018;41(8):1219-1227. doi: 10.1248/bpb.b18-00037. [PubMed:30068871 ]
Peng Y, Zhao S, Wu Y, Cao H, Xu Y, Liu X, Shui W, Cheng J, Zhao S, Shen L, Ma J, Quinn RJ, Stevens RC, Zhong G, Liu ZJ: Identification of natural products as novel ligands for the human 5-HT(2C) receptor. Biophys Rep. 2018;4(1):50-61. doi: 10.1007/s41048-018-0047-1. Epub 2018 Mar 9. [PubMed:29577069 ]
Mon MT, Yodkeeree S, Punfa W, Pompimon W, Limtrakul P: Alkaloids from Stephania venosa as Chemo-Sensitizers in SKOV3 Ovarian Cancer Cells via Akt/NF-kappaB Signaling. Chem Pharm Bull (Tokyo). 2018;66(2):162-169. doi: 10.1248/cpb.c17-00687. [PubMed:29386467 ]
LOTUS database [Link]

Showing NP-Card for (12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene (NP0265323)

MOL for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

3D MOL for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

3D SDF for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

3D-SDF for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

PDB for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

3D PDB for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

SMILES for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

INCHI for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

Structure for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)

3D Structure for NP0265323 ((12s)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene)