NP-MRD: Showing NP-Card for methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate (NP0147341)

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Record Information

Version

2.0

Created at

2022-09-02 02:55:57 UTC

Updated at

2022-09-02 02:55:58 UTC

NP-MRD ID

NP0147341

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate

Description

Methyl (1S,9S,10S,11E,14S,15S)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]Henicosa-2,4,6,16-tetraene-9-carboxylate belongs to the class of organic compounds known as pleiocarpaman alkaloids. These are alkaloids with a structure that is based on the pleiocarpaman skeleton. These alkaloids arise from the cyclization of a corynantheine precursor via C-16 to N-1. methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate is found in Alstonia angustifolia. Based on a literature review very few articles have been published on methyl (1S,9S,10S,11E,14S,15S)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]Henicosa-2,4,6,16-tetraene-9-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204552D          

 28 33  0  0  1  0            999 V2000
    6.4922    4.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4085    3.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6559    3.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5786    2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7982    1.6990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    1.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    1.8915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5325    2.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    3.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2549    4.0791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343    3.2965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    2.4638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3474    2.3151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7259    3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027    3.6064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9900    3.8252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8029    4.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052    5.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135    4.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    5.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2007    3.1702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513    2.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738    3.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8273    3.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583    2.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823    2.1671    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
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 12  1  1  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  1  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END

     RDKit          3D

 51 56  0  0  0  0  0  0  0  0999 V2000
    4.3800   -0.9390    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2707   -1.7743    0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9951   -1.5286    0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0067   -2.5258    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476   -2.2521    0.3901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0457   -2.0419   -0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -1.6306   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5628   -0.3749    0.0756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6692   -0.3269    0.9686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2897    0.4051    2.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0970    0.9599    3.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9956    0.5053    2.1325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4183   -0.1526    1.0082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7285   -1.4300    1.4549 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4554   -0.9093    2.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896   -0.3205    1.2975 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8757    0.7302    0.4892 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5892    0.9687   -0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0222    0.8896   -1.9307 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277    1.2934   -0.8114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6806    1.5377   -1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5299    0.7099    0.3055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452    1.5217   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0451    2.7360   -1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0092    3.2835   -2.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2212    2.6506   -2.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027    1.4568   -1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    0.8745   -0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2152   -0.2017    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958   -1.6145    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578   -0.5054   -0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5592   -2.7105   -0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -3.5445    0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1377   -2.7336   -0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -1.3658   -1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475   -3.0430   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9234   -1.5397   -1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0077   -2.4266   -0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8570    0.8083    4.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4074   -1.9300    2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -0.0547    2.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965   -1.7031    2.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2623    0.0787    2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655    1.7152    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858    2.3956   -2.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785    1.9198   -1.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7362    0.6432   -2.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    3.2079   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    4.2372   -2.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755    3.0941   -2.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4468    0.9567   -1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 10 12  2  0
 13 12  1  1
 13 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 22 17  1  0
 28 23  1  0
  3 16  1  0
 13 14  1  0
 13  8  1  0
 28  8  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 17 44  1  1
 16 43  1  1
 15 41  1  0
 15 42  1  0
 14 40  1  1
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
 11 39  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
  4 33  1  0
  4 34  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309022204552D          

 28 33  0  0  1  0            999 V2000
    6.4922    4.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4085    3.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6559    3.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5786    2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7982    1.6990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    1.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    1.8915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5325    2.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    3.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2549    4.0791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343    3.2965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    2.4638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3474    2.3151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7259    3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027    3.6064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9900    3.8252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8029    4.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052    5.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135    4.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    5.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2007    3.1702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513    2.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738    3.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8273    3.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583    2.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823    2.1671    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
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 12  1  1  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  1  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147341

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@@]45OC(O)=N[C@@]34N1C1=CC=CC=C51)C\C2=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C21H23N3O4/c1-3-12-11-23-9-8-20-14-6-4-5-7-15(14)24-17(18(25)27-2)13(12)10-16(23)21(20,24)22-19(26)28-20/h3-7,13,16-17H,8-11H2,1-2H3,(H,22,26)/b12-3-/t13-,16-,17-,20-,21+/m0/s1

> <INCHI_KEY>
MRMLDAGRWKCMNW-BIIXGJFKSA-N

> <FORMULA>
C21H23N3O4

> <MOLECULAR_WEIGHT>
381.432

> <EXACT_MASS>
381.168856233

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.38008171204389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,9S,10S,11E,14S,15S)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1^{10,14}.0^{1,15}.0^{2,7}.0^{8,15}]henicosa-2,4,6,16-tetraene-9-carboxylate

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
0.4829912796334538

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2769543169231556

> <JCHEM_PKA_STRONGEST_BASIC>
7.687745773002692

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
102.5963

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,9S,10S,11E,14S,15S)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1^{10,14}.0^{1,15}.0^{2,7}.0^{8,15}]henicosa-2,4,6,16-tetraene-9-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      12.119   7.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.963   6.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.558   5.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.413   3.977   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.957   3.172   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.855   1.918   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.252   2.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.639   3.531   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.727   4.734   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.096   6.356   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.209   7.614   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       6.784   6.154   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       6.708   4.599   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.115   4.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.822   5.663   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.152   6.732   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.448   7.140   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.099   8.640   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.223   9.693   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.625   9.088   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.276  10.588   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       5.975   5.918   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       4.202   5.580   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.938   6.459   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.544   5.803   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.416   4.268   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.680   3.389   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.074   4.045   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13   28                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14   22                                             
CONECT   14   13    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    3   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17   13   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23    8                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,9S,10S,11E,14S,15S)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1,.0,.0,.0,]henicosa-2,4,6,16-tetraene-9-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₃N₃O₄

Average Mass

381.4320 Da

Monoisotopic Mass

381.16886 Da

IUPAC Name

methyl (1S,9S,10S,11E,14S,15S)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1^{10,14}.0^{1,15}.0^{2,7}.0^{8,15}]henicosa-2,4,6,16-tetraene-9-carboxylate

Traditional Name

methyl (1S,9S,10S,11E,14S,15S)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1^{10,14}.0^{1,15}.0^{2,7}.0^{8,15}]henicosa-2,4,6,16-tetraene-9-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@@]45OC(O)=N[C@@]34N1C1=CC=CC=C51)C\C2=C\C

InChI Identifier

InChI=1S/C21H23N3O4/c1-3-12-11-23-9-8-20-14-6-4-5-7-15(14)24-17(18(25)27-2)13(12)10-16(23)21(20,24)22-19(26)28-20/h3-7,13,16-17H,8-11H2,1-2H3,(H,22,26)/b12-3-/t13-,16-,17-,20-,21+/m0/s1

InChI Key

MRMLDAGRWKCMNW-BIIXGJFKSA-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
Alstonia angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pleiocarpaman alkaloids. These are alkaloids with a structure that is based on the pleiocarpaman skeleton. These alkaloids arise from the cyclization of a corynantheine precursor via C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Pleiocarpaman alkaloids

Sub Class

Not Available

Direct Parent

Pleiocarpaman alkaloids

Alternative Parents

Substituents

Pleiocarpaman skeleton
Indolo[3,2-1de][1,5]naphthyridine
Alpha-amino acid ester
Beta-carboline
Pyridoindole
Diazanaphthalene
Alpha-amino acid or derivatives
Azaspirodecane
Naphthyridine
Quinolizidine
Indole or derivatives
Piperidinecarboxylic acid
Dialkylarylamine
Aralkylamine
Piperidine
Benzenoid
Oxazoline
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
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	1.89	ALOGPS
logP	0.48	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.28	ChemAxon
pKa (Strongest Basic)	7.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.6 m³·mol⁻¹	ChemAxon
Polarizability	39.38 Å³	ChemAxon
Number of Rings	6	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

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

163190268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate (NP0147341)

MOL for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

3D MOL for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

3D SDF for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

3D-SDF for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

PDB for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

3D PDB for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

SMILES for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

INCHI for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

Structure for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)

3D Structure for NP0147341 (methyl (1s,9s,10s,11e,14s,15s)-11-ethylidene-17-hydroxy-18-oxa-8,13,16-triazahexacyclo[11.5.2.1¹⁰,¹⁴.0¹,¹⁵.0²,⁷.0⁸,¹⁵]henicosa-2,4,6,16-tetraene-9-carboxylate)