NP-MRD: Showing NP-Card for methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0211625)

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Record Information

Version

2.0

Created at

2022-09-05 09:59:35 UTC

Updated at

2022-09-05 09:59:35 UTC

NP-MRD ID

NP0211625

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate

Description

(-)-Vincadifformine, also known as 6,7-dihydrotabersonine, belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids (-)-vincadifformine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate is found in Amsonia elliptica, Hunteria umbellata, Kopsia arborea, Melodinus fusiformis, Melodinus suaveolens, Rhazya stricta, Tabernaemontana grandiflora, Strempeliopsis strempelioides, Vallesia antillana and Vinca minor. methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate was first documented in 2019 (PMID: 31009114). Based on a literature review a small amount of articles have been published on (-)-vincadifformine (PMID: 33255314) (PMID: 35660549) (PMID: 36051302) (PMID: 31678034).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211592D          

 25 29  0  0  1  0            999 V2000
    0.1477    0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -0.0103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7883   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.2353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0999    0.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    1.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    2.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486    2.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785    3.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    0.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -0.5302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
  3 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 10 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25  7  1  1  0  0  0
  3 25  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -1.0497   -3.5501   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355   -2.4215    0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2137   -1.0910    0.1287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6929   -1.1552    0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553   -1.1760    1.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220    0.0076    2.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752    0.6998    1.8108 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794    1.8710    1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    2.0192   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    0.9718    0.1990 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8704    0.4884   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -0.3713   -1.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175   -0.8921   -2.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1970   -1.7244   -3.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752   -0.5270   -3.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6721   -1.0184   -4.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -0.8209   -1.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1658    1.0518   -1.0860 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4216    1.7615    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    2.4089    0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514    2.9433    1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4450    2.8241    2.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    2.1757    2.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044    1.6398    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5015   -0.0752    0.9751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0551   -3.4676   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3112   -3.8413   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -4.4580    0.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483   -2.6224    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5423   -2.2674    0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538   -0.2726   -0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1808   -2.0332    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.1425    2.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518   -1.2197    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -0.3205    3.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1367    0.7098    2.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465    1.9244    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6398    2.7359    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654    3.0392    0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186    1.9867   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -1.4285   -5.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123   -0.2395   -5.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196   -1.8729   -4.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568   -1.8256   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525   -0.1760   -1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8637    1.0073   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3924    2.4874   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4518    3.4530    2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    3.2522    3.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791    2.1075    2.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438   -0.5553    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  6
 10 25  1  0
 10 11  1  0
 11 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11 12  2  0
 12 17  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 25  3  1  0
 24 19  1  0
 17  3  1  0
 25  7  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 25 51  1  1
 18 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 17 44  1  0
 17 45  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
M  END


  Mrv1652309052211592D          

 25 29  0  0  1  0            999 V2000
    0.1477    0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -0.0103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7883   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.2353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0999    0.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    1.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    2.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486    2.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785    3.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    0.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -0.5302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
  3 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 10 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25  7  1  1  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211625

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CCCN3CC[C@@]4([C@H]13)C(NC1=CC=CC=C41)=C(C2)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-5,7-8,19,22H,3,6,9-13H2,1-2H3/t19-,20-,21-/m0/s1

> <INCHI_KEY>
GIGFIWJRTMBSRP-ACRUOGEOSA-N

> <FORMULA>
C21H26N2O2

> <MOLECULAR_WEIGHT>
338.451

> <EXACT_MASS>
338.199428085

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.409193263344804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_LOGP>
2.7938316726666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.07548098900882

> <JCHEM_PKA_STRONGEST_BASIC>
10.160718977333453

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
100.2852

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.276   0.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.714   0.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.910  -0.019   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.472  -0.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.229  -2.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.425  -3.061   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.863  -2.510   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.672  -2.928   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.512  -1.637   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.544  -0.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.786   1.082   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.591   2.052   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.833   3.573   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.271   4.123   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.637   4.543   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.880   6.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.152   1.502   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.308   1.321   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       8.005  -0.052   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.493  -0.452   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.890  -1.940   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.799  -3.028   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.312  -2.628   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.915  -1.140   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.106  -0.990   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17   25                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   24   25                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12    3                                                       
CONECT   18   11   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   10                                                  
CONECT   25   10    7    3                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(5alpha,12beta,19alpha)-2,3-Didehydroaspidospermidine-3-carboxylic acid methyl ester	ChEBI
6,7-Dihydrotabersonine	ChEBI
Methyl (5S,12R,19S)-2,3-didehydroaspidospermidine-3-carboxylate	ChEBI
Vincadifformine	ChEBI
(5a,12b,19a)-2,3-Didehydroaspidospermidine-3-carboxylate methyl ester	Generator
(5a,12b,19a)-2,3-Didehydroaspidospermidine-3-carboxylic acid methyl ester	Generator
(5alpha,12beta,19alpha)-2,3-Didehydroaspidospermidine-3-carboxylate methyl ester	Generator
(5Α,12β,19α)-2,3-didehydroaspidospermidine-3-carboxylate methyl ester	Generator
(5Α,12β,19α)-2,3-didehydroaspidospermidine-3-carboxylic acid methyl ester	Generator
Methyl (5S,12R,19S)-2,3-didehydroaspidospermidine-3-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₆N₂O₂

Average Mass

338.4510 Da

Monoisotopic Mass

338.19943 Da

IUPAC Name

methyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

Traditional Name

methyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@@]12CCCN3CC[C@@]4([C@H]13)C(NC1=CC=CC=C41)=C(C2)C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-5,7-8,19,22H,3,6,9-13H2,1-2H3/t19-,20-,21-/m0/s1

InChI Key

GIGFIWJRTMBSRP-ACRUOGEOSA-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
Amsonia elliptica	LOTUS Database	35616633
Hunteria umbellata	LOTUS Database	35616633
Kopsia arborea	LOTUS Database	35616633
Melodinus fusiformis	LOTUS Database	35616633
Melodinus suaveolens	LOTUS Database	35616633
Rhazya stricta	LOTUS Database	35616633
Stemmadenia grandiflora	LOTUS Database	35616633
Strempeliopsis strempelioides	LOTUS Database	35616633
Vallesia antillana	LOTUS Database	35616633
Vinca minor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Plumeran-type alkaloid
Carbazole
Indole or derivatives
Dihydroindole
Indolizidine
Secondary aliphatic/aromatic amine
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Monocarboxylic acid or derivatives
Enamine
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Secondary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:70507 )

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	2.79	ChemAxon
pKa (Strongest Acidic)	14.08	ChemAxon
pKa (Strongest Basic)	10.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.29 m³·mol⁻¹	ChemAxon
Polarizability	38.41 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

C00024463

Chemspider ID

85064

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94255

PDB ID

Not Available

ChEBI ID

70507

Good Scents ID

Not Available

References

General References

Stander EA, Sepulveda LJ, Duge de Bernonville T, Carqueijeiro I, Koudounas K, Lemos Cruz P, Besseau S, Lanoue A, Papon N, Giglioli-Guivarc'h N, Dirks R, O'Connor SE, Atehortua L, Oudin A, Courdavault V: Identifying Genes Involved in alkaloid Biosynthesis in Vinca minor Through Transcriptomics and Gene Co-Expression Analysis. Biomolecules. 2020 Nov 24;10(12). pii: biom10121595. doi: 10.3390/biom10121595. [PubMed:33255314 ]
Williams D, Qu Y, Simionescu R, De Luca V: The assembly of (+)-vincadifformine- and (-)-tabersonine-derived monoterpenoid indole alkaloids in Catharanthus roseus involves separate branch pathways. Plant J. 2019 Aug;99(4):626-636. doi: 10.1111/tpj.14346. Epub 2019 May 21. [PubMed:31009114 ]
Williams D, Brzezinski W, Gordon H, De Luca V: Site directed mutagenesis of Catharanthus roseus (+)-vincadifformine 19-hydroxylase (CYP71BY3) results in two distinct enzymatic functions. Phytochemistry. 2022 Sep;201:113265. doi: 10.1016/j.phytochem.2022.113265. Epub 2022 Jun 2. [PubMed:35660549 ]
Palumbo F, Draga S, Scariolo F, Gabelli G, Sacilotto GB, Gazzola M, Barcaccia G: First genomic insights into the Mandevilla genus. Front Plant Sci. 2022 Aug 16;13:983879. doi: 10.3389/fpls.2022.983879. eCollection 2022. [PubMed:36051302 ]
Anjali KP, Sangeetha BM, Devi G, Raghunathan R, Dutta S: Bioprospecting of seaweeds (Ulva lactuca and Stoechospermum marginatum): The compound characterization and functional applications in medicine-a comparative study. J Photochem Photobiol B. 2019 Nov;200:111622. doi: 10.1016/j.jphotobiol.2019.111622. Epub 2019 Sep 10. [PubMed:31678034 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0211625)

MOL for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D MOL for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D SDF for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D-SDF for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

PDB for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D PDB for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

SMILES for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

INCHI for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

Structure for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D Structure for NP0211625 (methyl (1r,12s,19s)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)