NP-MRD: Showing NP-Card for 2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol (NP0167742)

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Record Information

Version

2.0

Created at

2022-09-03 03:24:21 UTC

Updated at

2022-09-03 03:24:21 UTC

NP-MRD ID

NP0167742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol

Description

18-Hydroxyaffinisine belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. 2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol is found in Tabernaemontana cymosa. Based on a literature review very few articles have been published on 18-Hydroxyaffinisine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205242D          

 24 28  0  0  1  0            999 V2000
    3.0922   -1.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497   -1.1217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    0.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738    0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2030    0.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6237    0.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -0.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3946   -0.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5986   -0.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288   -0.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324    0.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8962   -0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -1.6746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4347   -0.4896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2463   -1.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423   -0.6965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9445    0.3975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302    0.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696    0.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5555    1.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538    1.9740    0.0000 O   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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  2 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 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
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    2.0864    2.4739    1.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    1.3519    0.8892 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    0.6644    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -0.3028   -0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0547   -0.1785   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0653   -0.8945   -1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857   -0.5745   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228    0.4648    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6344    1.1852    0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3213    0.8569    0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901   -1.2408   -1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476   -0.8479   -1.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5214   -1.7295   -0.4282 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8992   -2.9860    0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9051   -3.7167    0.7390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770   -0.8996    0.7381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8653   -0.2401    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2873    0.7716    0.4577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7899    0.5404   -0.9073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    1.0011   -0.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    0.1642    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1331    0.3660    0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8712    1.4535   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3363    2.3539    0.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0279    2.8158    1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4137    2.1087    2.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670    3.3422    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015   -1.6981   -1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -1.1323   -1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6733    0.7216    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9233    1.9916    1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244   -1.2580   -2.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9923   -2.2526   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069   -0.9338   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4474   -2.0337   -1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0962   -2.7830    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5764   -3.6420   -0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -3.7463    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6419   -1.5230    1.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.9890    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331    0.2597    2.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125    1.7778    0.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    2.0384   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6032    0.9268   -1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6907   -0.2383    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7178    1.0830   -0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1869    2.0381   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6712    3.0899    0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3 18  1  0
 18 17  1  0
 17 16  1  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 13 12  1  0
 12 11  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
  3  2  1  0
 19 18  1  0
  5 10  1  0
 11  4  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  9 31  1  0
  8 30  1  0
  7 29  1  0
  6 28  1  0
 18 42  1  1
 17 40  1  0
 17 41  1  0
 16 39  1  1
 13 35  1  6
 14 36  1  0
 14 37  1  0
 15 38  1  0
 12 34  1  6
 11 32  1  0
 11 33  1  0
 20 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
M  END


  Mrv1652309032205242D          

 24 28  0  0  1  0            999 V2000
    3.0922   -1.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497   -1.1217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    0.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738    0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2030    0.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6237    0.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -0.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3946   -0.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5986   -0.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288   -0.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2324    0.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8962   -0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -1.6746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4347   -0.4896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2463   -1.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423   -0.6965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9445    0.3975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302    0.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696    0.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5555    1.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538    1.9740    0.0000 O   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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  2 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 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
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=CC=CC=C2C2=C1[C@@H]1C[C@@H]3C(CO)C(C2)N1C\C3=C/CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O2/c1-21-17-5-3-2-4-13(17)15-9-18-16(11-24)14-8-19(20(15)21)22(18)10-12(14)6-7-23/h2-6,14,16,18-19,23-24H,7-11H2,1H3/b12-6+/t14-,16?,18?,19-/m0/s1

> <INCHI_KEY>
LQAOSRRYWHBXPK-WDKJBEHZSA-N

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.424

> <EXACT_MASS>
324.183778021

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.40456833768674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,14R,15Z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethan-1-ol

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.151352276666667

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.828187510649148

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.198122395710051

> <JCHEM_PKA_STRONGEST_BASIC>
6.207019356460614

> <JCHEM_POLAR_SURFACE_AREA>
48.629999999999995

> <JCHEM_REFRACTIVITY>
95.99219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,14R,15Z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.772  -3.645   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.319  -2.094   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.905  -1.484   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.049   0.049   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.551   0.387   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.306   1.730   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.846   1.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.631   0.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.876  -0.920   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.337  -0.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.984  -1.557   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.547  -0.324   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.434   0.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.673  -1.406   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.626  -3.126   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.812  -0.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.460  -1.976   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.946  -1.300   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.763   0.742   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.430   1.848   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.063   0.973   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.484   1.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.904   3.297   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.394   3.685   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5    2                                                  
CONECT   11    4   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17    3   19                                                  
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N₂O₂

Average Mass

324.4240 Da

Monoisotopic Mass

324.18378 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CN1C2=CC=CC=C2C2=C1[C@@H]1C[C@@H]3C(CO)C(C2)N1C\C3=C/CO

InChI Identifier

InChI=1S/C20H24N2O2/c1-21-17-5-3-2-4-13(17)15-9-18-16(11-24)14-8-19(20(15)21)22(18)10-12(14)6-7-23/h2-6,14,16,18-19,23-24H,7-11H2,1H3/b12-6+/t14-,16?,18?,19-/m0/s1

InChI Key

LQAOSRRYWHBXPK-WDKJBEHZSA-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
Tabernaemontana cymosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Quinuclidine
Aralkylamine
Benzenoid
N-methylpyrrole
Piperidine
Substituted pyrrole
Pyrrole
1,3-aminoalcohol
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.61	ALOGPS
logP	1.15	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.2	ChemAxon
pKa (Strongest Basic)	6.21	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101927633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol (NP0167742)

MOL for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

3D MOL for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

3D SDF for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

3D-SDF for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

PDB for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

3D PDB for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

SMILES for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

INCHI for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

Structure for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)

3D Structure for NP0167742 (2-[(1s,14r,15z)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-15-ylidene]ethanol)