NP-MRD: Showing NP-Card for methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate (NP0252989)

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Record Information

Version

2.0

Created at

2022-09-07 16:42:45 UTC

Updated at

2022-09-07 16:42:45 UTC

NP-MRD ID

NP0252989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate

Description

Voachalotine 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. methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate is found in Tabernaemontana corymbosa, Tabernaemontana cymosa, Tabernaemontana hystrix and Tabernaemontana solanifolia. methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate was first documented in 2011 (PMID: 21892126). Based on a literature review a small amount of articles have been published on Voachalotine (PMID: 35075954) (PMID: 33321518) (PMID: 30599414) (PMID: 23983637).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218422D          

 27 31  0  0  1  0            999 V2000
   -1.4389   -0.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    0.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    0.6214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8938    0.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650    0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -0.2352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8279   -0.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616   -1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496   -2.2474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -1.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -2.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720   -1.4258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -2.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.3360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2834   -0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490    0.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038    1.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3826    1.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834    0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533    0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16  5  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 18 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.8079   -2.5821    0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330   -1.7310    1.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -0.9422    1.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486   -0.0239    2.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917    0.2543    1.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -1.0259    0.8863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4691   -1.5166   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351   -0.8966   -0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6967    0.5878   -0.4163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6741    0.6642   -1.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580    2.0041   -2.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    1.2963    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8058    0.6870    0.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1047    2.6342   -0.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410    3.3827    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602    1.0949    0.2641 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7068    1.3541   -0.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815    0.4677   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672   -0.7079    0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9688   -1.2929    0.4184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2774   -2.5418    1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -0.5538   -0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459   -0.7060   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469    0.2296   -1.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991    1.3280   -1.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524    1.4633   -1.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074    0.5436   -0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5343   -3.1648    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -3.3426    0.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4466   -1.9921    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894   -1.7204    2.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703    0.9058    2.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8722   -0.5561    3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184   -1.7286    1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0374   -1.3512   -1.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6327   -2.6314   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516   -1.4261   -0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622    0.2645   -2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.0643   -2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328    2.1284   -3.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9406    4.1343    0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0535    2.7146    0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6037    3.9964   -0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7702    2.0681    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973    2.3985   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743    1.3919   -1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794   -3.0134    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5630   -2.3141    2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4238   -3.2668    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7830   -1.5615   -0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0218    0.1247   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8289    2.0835   -2.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223    2.3230   -1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
  9 12  1  1
  9 10  1  0
 10 11  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  3  4  1  0
  4  5  1  0
  3  2  2  0
  2  1  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
  8  9  1  0
 27 22  1  0
  5 16  1  0
 27 18  1  0
  5  6  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
  6 34  1  1
  7 35  1  0
  7 36  1  0
  8 37  1  6
  4 32  1  0
  4 33  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
M  END


  Mrv1652309072218422D          

 27 31  0  0  1  0            999 V2000
   -1.4389   -0.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    0.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    0.6214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8938    0.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650    0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -0.2352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8279   -0.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616   -1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496   -2.2474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -1.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -2.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720   -1.4258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -2.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.3360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2834   -0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490    0.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038    1.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3826    1.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834    0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533    0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16  5  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 18 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(CO)[C@@H]2CC3=C(C4C[C@H]1\C(CN24)=C/C)N(C)C1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4-/t16-,18?,19-,22?/m0/s1

> <INCHI_KEY>
IWEYXWIPVZEVPT-RAVRWMCNSA-N

> <FORMULA>
C22H26N2O3

> <MOLECULAR_WEIGHT>
366.461

> <EXACT_MASS>
366.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.60932443027827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (12S,14S,15E)-15-ethylidene-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-tetraene-13-carboxylate

> <JCHEM_LOGP>
2.2620616713333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.808028891587885

> <JCHEM_PKA_STRONGEST_BASIC>
6.142185208417517

> <JCHEM_POLAR_SURFACE_AREA>
54.699999999999996

> <JCHEM_REFRACTIVITY>
105.0467

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (12S,14S,15E)-15-ethylidene-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-tetraene-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.686  -0.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.025   0.455   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.490   0.578   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.536   1.770   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.020   1.160   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.535   1.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.175   0.220   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.719  -0.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.545  -1.756   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.302  -2.664   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.466  -4.195   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.539  -2.933   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.016  -4.382   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.054  -2.662   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.047  -3.839   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.707  -0.627   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.262  -1.045   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.645  -0.284   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.131   1.168   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       6.354   2.105   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       6.314   3.644   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.622   1.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.120   1.591   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.180   0.473   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.741  -1.003   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.244  -1.362   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.184  -0.244   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   16                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   12   16                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    9    5   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18    6   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   18   22                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₂O₃

Average Mass

366.4610 Da

Monoisotopic Mass

366.19434 Da

IUPAC Name

methyl (12S,14S,15E)-15-ethylidene-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-tetraene-13-carboxylate

Traditional Name

methyl (12S,14S,15E)-15-ethylidene-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-tetraene-13-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(CO)[C@@H]2CC3=C(C4C[C@H]1\C(CN24)=C/C)N(C)C1=CC=CC=C31

InChI Identifier

InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4-/t16-,18?,19-,22?/m0/s1

InChI Key

IWEYXWIPVZEVPT-RAVRWMCNSA-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 corymbosa	LOTUS Database	35616633
Tabernaemontana cymosa	LOTUS Database	35616633
Tabernaemontana hystrix	LOTUS Database	35616633
Tabernaemontana solanifolia	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
Corynanthean skeleton
Vobasan skeleton
Pyridoindole
Beta-carboline
N-alkylindole
3-alkylindole
Piperidinecarboxylic acid
Indole or derivatives
Indole
Quinuclidine
Aralkylamine
Beta-hydroxy acid
Benzenoid
Substituted pyrrole
Piperidine
N-methylpyrrole
Hydroxy acid
Heteroaromatic compound
Methyl ester
Pyrrole
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.26	ChemAxon
pKa (Strongest Acidic)	14.81	ChemAxon
pKa (Strongest Basic)	6.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.05 m³·mol⁻¹	ChemAxon
Polarizability	40.61 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

C00026687

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

134716706

PDB ID

Not Available

ChEBI ID

181722

Good Scents ID

Not Available

References

General References

Reis FL, Adolpho L, Ruiz ALTG, Simionatto E, Dalcol II, Mostardeiro MA, Morel AF: In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res. 2022 Jan 25:1-5. doi: 10.1080/14786419.2021.2017928. [PubMed:35075954 ]
Musquiari B, Crevelin EJ, Bertoni BW, Franca SC, Pereira AMS, Castello ACD, Castillo-Ordonez WO, Giuliatti S, Lopes AA: Precursor-directed Biosynthesis in Tabernaemontana catharinensis as a New Avenue for Alzheimer's Disease-modifying Agents. Planta Med. 2021 Feb;87(1-02):136-147. doi: 10.1055/a-1315-2282. Epub 2020 Dec 15. [PubMed:33321518 ]
Rosales PF, Marinho FF, Gower A, Chiarello M, Canci B, Roesch-Ely M, Paula FR, Moura S: Bio-guided search of active indole alkaloids from Tabernaemontana catharinensis: Antitumour activity, toxicity in silico and molecular modelling studies. Bioorg Chem. 2019 Apr;85:66-74. doi: 10.1016/j.bioorg.2018.12.016. Epub 2018 Dec 15. [PubMed:30599414 ]
Nicola C, Salvador M, Gower AE, Moura S, Echeverrigaray S: Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal. 2013 Jul 28;2013:519858. doi: 10.1155/2013/519858. eCollection 2013. [PubMed:23983637 ]
Goncalves MS, Vieira IJ, Oliveira RR, Braz-Filho R: Application of preparative high-speed counter-current chromatography for the separation of two alkaloids from the roots of Tabernaemontana catharinensis (Apocynaceae). Molecules. 2011 Sep 2;16(9):7480-7. doi: 10.3390/molecules16097480. [PubMed:21892126 ]
LOTUS database [Link]

Showing NP-Card for methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate (NP0252989)

MOL for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

3D MOL for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

3D SDF for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

3D-SDF for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

PDB for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

3D PDB for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

SMILES for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

INCHI for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

Structure for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)

3D Structure for NP0252989 (methyl (12s,14s,15e)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate)