NP-MRD: Showing NP-Card for (1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium (NP0206908)

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Record Information

Version

2.0

Created at

2022-09-05 03:19:23 UTC

Updated at

2022-09-05 03:19:24 UTC

NP-MRD ID

NP0206908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium

Description

Fuchsiaefoline 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. (1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium is found in Tabernaemontana hystrix. (1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium was first documented in 2004 (PMID: 14723540). Based on a literature review very few articles have been published on Fuchsiaefoline (PMID: 16388644).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052205192D          

 29 33  0  0  1  0            999 V2000
   -1.5535    0.9227    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  3  0  0  0  0  0  0  0  0  0  0
    1.2242    1.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.3360    0.0000 C   0  0  0  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
    5.1205    1.6430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9228    1.8352    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
    1.8938    0.6568    0.0000 C   0  0  2  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
    0.7294   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -2.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895   -2.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -3.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9510   -3.5687    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
 13 20  1  0  0  0  0
 21 10  1  6  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  1   5   1
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
   -3.3392    4.8836   -1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090    3.7142   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    2.8026   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679    2.8362   -1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160    1.5779   -1.3756 N   0  0  1  0  0  4  0  0  0  0  0  0
    0.3725    1.6241   -2.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    1.6190   -0.1199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8937    1.6038    1.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    1.6242    0.4789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5522    0.4323   -0.4382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6904   -0.8200    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7201   -1.5157    0.1362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409   -1.3127    1.1891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175   -2.5331    1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0663   -3.7132    0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    0.4481   -1.4992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7477   -0.8546   -1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -0.7457   -0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    0.3965   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0996    0.1414    0.6146 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8484    1.1066    1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989   -1.1385    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5153   -1.8503    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4806   -1.2385    1.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5883   -2.0113    2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -3.1737    0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -3.8052   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5872   -3.0680   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323   -1.7311   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3188    5.3951   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2333    4.5361   -2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5596    5.5846   -0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0592    3.6544    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    3.6385   -1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967    2.9648   -2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954    2.2762   -2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0508    2.1441   -3.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974    0.6440   -2.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7153    2.5429   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7794    2.5666    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    0.7845    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0400    1.6586    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325    0.6328   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0470   -2.6757    2.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8305   -2.5118    2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -3.7703    0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -3.7966    0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327   -4.6353    1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384    0.5357   -2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284   -1.7033   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4420   -1.1522   -2.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286    1.4026    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    0.6818    2.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509    2.0134    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1312   -2.4834    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3003   -1.3159    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3036   -2.7537    2.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4644   -3.7866    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7703   -4.8409   -0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8251   -3.5302   -1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  1  0
 16  5  1  0
  5  6  1  6
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 18 29  1  0
 29 28  2  0
 28 27  1  0
 27 26  2  0
 26 23  1  0
 23 24  1  0
 24 25  1  0
 23 22  2  0
 22 20  1  0
 20 21  1  0
 16 10  1  0
 22 29  1  0
  3  9  1  0
  5  7  1  0
 20 19  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 14 44  1  0
 14 45  1  0
 10 43  1  6
  9 42  1  1
  8 40  1  0
  8 41  1  0
  7 39  1  6
 17 50  1  0
 17 51  1  0
 16 49  1  6
  6 36  1  0
  6 37  1  0
  6 38  1  0
  4 34  1  0
  4 35  1  0
  2 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 28 60  1  0
 27 59  1  0
 26 58  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
M  CHG  1   5   1
M  END


  Mrv1652309052205192D          

 29 33  0  0  1  0            999 V2000
   -1.5535    0.9227    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  3  0  0  0  0  0  0  0  0  0  0
    1.2242    1.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.3360    0.0000 C   0  0  0  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
    5.1205    1.6430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9228    1.8352    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
    1.8938    0.6568    0.0000 C   0  0  2  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
    0.7294   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -2.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895   -2.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -3.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9510   -3.5687    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
 13 20  1  0  0  0  0
 21 10  1  6  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  1   5   1
M  END
> <DATABASE_ID>
NP0206908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C1[C@H]2C[C@H]3C4=C(CC1[N+]3(C)C\C2=C/C)C1=CC=CC(OC)=C1N4C

> <INCHI_IDENTIFIER>
InChI=1S/C24H31N2O3/c1-6-14-13-26(4)18-12-17-15-9-8-10-20(28-5)23(15)25(3)22(17)19(26)11-16(14)21(18)24(27)29-7-2/h6,8-10,16,18-19,21H,7,11-13H2,1-5H3/q+1/b14-6+/t16-,18?,19-,21?,26?/m0/s1

> <INCHI_KEY>
QYLOWVPDEGEWFW-DAXJUTDDSA-N

> <FORMULA>
C24H31N2O3

> <MOLECULAR_WEIGHT>
395.522

> <EXACT_MASS>
395.232919286

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.59325734634706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,14R,15Z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium

> <JCHEM_LOGP>
-0.9763814014717451

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.880981432145696

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
125.89639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,14R,15Z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium

> <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      -2.900   1.722   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+1
HETATM    6  C   UNK     0       2.285   2.677   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.707  -0.627   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.262  -1.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.645  -0.284   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.131   1.168   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.354   2.105   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.314   3.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.622   1.232   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.120   1.591   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.558   3.067   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.056   3.426   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.180   0.473   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.741  -1.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.244  -1.362   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.184  -0.244   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.535   1.226   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.175   0.220   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.719  -0.439   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.545  -1.756   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.362  -3.285   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.055  -3.890   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.594  -4.209   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.410  -5.738   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.642  -6.662   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   21                                             
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    9   13                                                  
CONECT   21   10    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23    7   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₁N₂O₃

Average Mass

395.5220 Da

Monoisotopic Mass

395.23292 Da

IUPAC Name

(1S,14R,15Z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium

Traditional Name

(1S,14R,15Z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1[C@H]2C[C@H]3C4=C(CC1[N+]3(C)C\C2=C/C)C1=CC=CC(OC)=C1N4C

InChI Identifier

InChI=1S/C24H31N2O3/c1-6-14-13-26(4)18-12-17-15-9-8-10-20(28-5)23(15)25(3)22(17)19(26)11-16(14)21(18)24(27)29-7-2/h6,8-10,16,18-19,21H,7,11-13H2,1-5H3/q+1/b14-6+/t16-,18?,19-,21?,26?/m0/s1

InChI Key

QYLOWVPDEGEWFW-DAXJUTDDSA-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 hystrix	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Anisole
Quinuclidine
Phenol ether
Aralkylamine
Alkyl aryl ether
Benzenoid
Substituted pyrrole
Piperidine
N-methylpyrrole
Heteroaromatic compound
Quaternary ammonium salt
Pyrrole
Tetraalkylammonium salt
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic cation
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	-0.98	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	125.9 m³·mol⁻¹	ChemAxon
Polarizability	45.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00026685

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

102357237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou H, Liao X, Yin W, Ma J, Cook JM: General approach for the synthesis of 12-methoxy-substituted sarpagine indole alkaloids including (-)-12-methoxy-N(b)-methylvoachalotine, (+)-12-methoxy-N(a)-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline. J Org Chem. 2006 Jan 6;71(1):251-9. doi: 10.1021/jo052081t. [PubMed:16388644 ]
Zhou H, Liao X, Cook JM: Regiospecific, enantiospecific total synthesis of the 12-alkoxy-substituted indole alkaloids, (+)-12-methoxy-Na-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline. Org Lett. 2004 Jan 22;6(2):249-52. doi: 10.1021/ol0362212. [PubMed:14723540 ]
LOTUS database [Link]

Showing NP-Card for (1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium (NP0206908)

MOL for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

3D MOL for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

3D SDF for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

3D-SDF for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

PDB for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

3D PDB for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

SMILES for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

INCHI for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

Structure for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)

3D Structure for NP0206908 ((1s,14r,15z)-13-(ethoxycarbonyl)-15-ethylidene-5-methoxy-3,17-dimethyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium)