NP-MRD: Showing NP-Card for methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate (NP0153585)

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Record Information

Version

2.0

Created at

2022-09-02 10:16:14 UTC

Updated at

2022-09-02 10:16:14 UTC

NP-MRD ID

NP0153585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate

Description

Methyl (1R,9R,11S,14S,19R)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Icosa-2,4,6-triene-10-carboxylate 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. methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate is found in Catharanthus ovalis. Based on a literature review very few articles have been published on methyl (1R,9R,11S,14S,19R)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Icosa-2,4,6-triene-10-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212162D          

 32 37  0  0  1  0            999 V2000
    0.9506    0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570   -0.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3806   -1.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073   -0.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024    0.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    1.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1537    1.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    1.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032    2.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    0.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8809    0.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872   -0.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115   -0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -1.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    0.2040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0751    0.7244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199    1.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918    0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787   -0.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9801   -0.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873   -1.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -0.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7335   -0.6222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3123   -1.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732   -2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -1.9268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038   -2.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -1.8958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0592   -2.3232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -1.0935    0.0000 C   0  0  1  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  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 17 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
 25 24  1  6  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 28  1  1  0  0  0
  3 32  1  0  0  0  0
 25 32  1  0  0  0  0
M  END

     RDKit          3D

 62 67  0  0  0  0  0  0  0  0999 V2000
    1.4072   -2.9804    0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9213    0.5876   -2.1954 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7371    1.0534   -0.8843 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4061    2.3504   -0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    2.8517    0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0395    3.0456   -1.6876 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    4.2817   -1.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3386   -0.0176    0.0061 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9286    0.0271    1.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977    0.1049    2.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621    0.1571    3.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1055    0.1319    2.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    1.0960   -0.6614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1837    2.0201    0.3439 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    3.4582    0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6018    1.2481    1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8624    1.5985    2.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2679    0.6536    3.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -0.6671    3.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538   -1.0487    1.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -0.0667    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929   -0.2048   -0.3509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6951   -0.2685   -1.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -1.4941   -1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657   -2.0387   -1.7531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5266   -2.4075   -2.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -1.5513   -3.2624 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.6139   -1.4276   -0.6504 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.2897    4.6639   -2.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    0.0073   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    1.1697    4.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219   -0.0831    3.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524   -0.5713    4.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641    1.5142   -1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449    3.9187   -0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    3.9518    1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765    3.7768    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7417    2.6459    3.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4805    0.9102    4.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7306   -1.3868    4.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -2.0850    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11  3  1  0
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 30  4  1  0
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 32 62  1  1
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 10 41  1  0
M  END


  Mrv1652309022212162D          

 32 37  0  0  1  0            999 V2000
    0.9506    0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570   -0.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3806   -1.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073   -0.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024    0.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    1.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1537    1.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    1.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032    2.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    0.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8809    0.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2115   -0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -1.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    0.2040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0751    0.7244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199    1.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918    0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787   -0.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9801   -0.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873   -1.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -0.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7335   -0.6222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3123   -1.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732   -2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -1.9268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038   -2.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -1.8958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0592   -2.3232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -1.0935    0.0000 C   0  0  1  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  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
  3 11  1  0  0  0  0
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 13 15  2  0  0  0  0
  6 16  1  0  0  0  0
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 19 24  1  0  0  0  0
 25 24  1  6  0  0  0
 16 25  1  0  0  0  0
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 26 27  1  0  0  0  0
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 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 28  1  1  0  0  0
  3 32  1  0  0  0  0
 25 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC12C3OC([C@H]1OC(C)=O)([C@@H]1N(C)C4=CC=CC=C4[C@@]11CCN(C[C@@H]3O)[C@@H]21)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H30N2O6/c1-5-22-17-16(28)12-26-11-10-23(18(22)26)14-8-6-7-9-15(14)25(3)19(23)24(32-17,21(29)30-4)20(22)31-13(2)27/h6-9,16-20,28H,5,10-12H2,1-4H3/t16-,17?,18-,19+,20-,22?,23+,24?/m0/s1

> <INCHI_KEY>
GUGWEFILCHULQR-KXNSEQTKSA-N

> <FORMULA>
C24H30N2O6

> <MOLECULAR_WEIGHT>
442.512

> <EXACT_MASS>
442.210386694

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.7842417521583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,9R,11S,14S,19R)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1^{10,13}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2,4,6-triene-10-carboxylate

> <JCHEM_LOGP>
1.414126735

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.804004014702116

> <JCHEM_PKA_STRONGEST_BASIC>
9.634297915645602

> <JCHEM_POLAR_SURFACE_AREA>
88.54

> <JCHEM_REFRACTIVITY>
113.93119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,9R,11S,14S,19R)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1^{10,13}.0^{1,9}.0^{2,7}.0^{16,19}]icosa-2,4,6-triene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.774   1.639   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.786  -0.182   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.580  -1.353   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.710  -1.869   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.947  -0.186   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.938   0.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.593   2.302   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.154   3.198   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.577   3.451   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.193   4.942   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.051   0.329   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.644   0.878   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.589  -0.608   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.128  -0.543   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.877  -1.974   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.653   0.381   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.873   1.352   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.517   2.869   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.211   0.575   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.691   1.002   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.800  -0.067   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.430  -1.562   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.950  -1.988   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.841  -0.919   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.236  -1.161   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.316  -2.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.683  -3.849   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       2.121  -3.597   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       0.754  -4.372   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.609  -3.539   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.977  -4.337   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.964  -2.041   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11   32                                             
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11   16                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    6    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6   17   25                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   16   26   32                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29    4   31                                                  
CONECT   31   30                                                            
CONECT   32   28    3   25                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,9R,11S,14S,19R)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1,.0,.0,.0,]icosa-2,4,6-triene-10-carboxylic acid	Generator

Chemical Formula

C₂₄H₃₀N₂O₆

Average Mass

442.5120 Da

Monoisotopic Mass

442.21039 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC12C3OC([C@H]1OC(C)=O)([C@@H]1N(C)C4=CC=CC=C4[C@@]11CCN(C[C@@H]3O)[C@@H]21)C(=O)OC

InChI Identifier

InChI=1S/C24H30N2O6/c1-5-22-17-16(28)12-26-11-10-23(18(22)26)14-8-6-7-9-15(14)25(3)19(23)24(32-17,21(29)30-4)20(22)31-13(2)27/h6-9,16-20,28H,5,10-12H2,1-4H3/t16-,17?,18-,19+,20-,22?,23+,24?/m0/s1

InChI Key

GUGWEFILCHULQR-KXNSEQTKSA-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
Catharanthus ovalis	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
Quinolidine
Indolizidine
Indole or derivatives
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Aralkylamine
Oxepane
Benzenoid
N-alkylpyrrolidine
Piperidine
Dicarboxylic acid or derivatives
Methyl ester
Tetrahydrofuran
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
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

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

163187996

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate (NP0153585)

MOL for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

3D MOL for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

3D SDF for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

3D-SDF for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

PDB for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

3D PDB for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

SMILES for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

INCHI for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

Structure for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)

3D Structure for NP0153585 (methyl (1r,9r,11s,14s,19r)-11-(acetyloxy)-12-ethyl-14-hydroxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.1¹⁰,¹³.0¹,⁹.0²,⁷.0¹⁶,¹⁹]icosa-2,4,6-triene-10-carboxylate)