NP-MRD: Showing NP-Card for (1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate (NP0154821)

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Record Information

Version

2.0

Created at

2022-09-02 11:47:11 UTC

Updated at

2022-09-02 11:47:12 UTC

NP-MRD ID

NP0154821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate

Description

Methyl (1R,2S,3R,5R,10S)-2,6-dimethyl-8,20-dioxo-8λ⁵-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]Icosa-13(19),16-diene-17-carboxylate belongs to the class of organic compounds known as yuzurimine-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum that contain a 22 carbon core, commonly with a C9-C10 double bond, and C-22 is mostly a methyl ester of a carboxyl group. Based on a literature review very few articles have been published on methyl (1R,2S,3R,5R,10S)-2,6-dimethyl-8,20-dioxo-8λ⁵-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]Icosa-13(19),16-diene-17-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213472D          

 28 33  0  0  1  0            999 V2000
    4.4096   -0.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505    0.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427    0.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939    0.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837    1.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525    2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460    2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289    3.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234    3.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0278    2.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    2.5492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3052    1.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    1.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    1.8785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7554    2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349    3.2175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7097    3.2842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5089    3.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    4.1388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4996    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729    4.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262    4.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    3.7295    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.2127    4.3279    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3410    3.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    2.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9297    1.8440    0.0000 C   0  0  0  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  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
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 20 23  1  1  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  CHG  2  24   1  25  -1
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    5.0003    2.9737    1.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    2.0661    1.4450 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    1.6748    0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2768    2.1785   -0.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023    0.7531   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864    0.3142   -1.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649    0.3439   -2.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -0.9282   -3.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8522   -1.4182   -2.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9529   -0.5625   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508   -0.1621    0.1742 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6660    0.0906    0.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1955    1.2342    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116    1.9918   -0.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    1.7344    1.0393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3132    0.7288    2.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757   -0.5446    1.5294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4593   -1.2031    0.8032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3664   -1.9068    1.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308   -2.1956    0.0546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1661   -2.4724   -1.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -2.7394   -2.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7438   -1.8885    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5580   -0.4956    0.4915 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.1620   -0.1728   -0.7595 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.4646    0.4798    0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6569    1.7773    0.5182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7831    2.1247   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364    3.7045    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8513    2.3574    2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352    3.4726    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068    1.2494   -3.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    0.3455   -3.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122   -1.6718   -3.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523   -0.7915   -4.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751    0.8147    1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528   -0.8595    1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    2.7097    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182    0.9959    2.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    0.7705    2.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327   -1.2775    2.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3666   -2.6249    2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755   -2.5563    1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583   -1.2262    2.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -3.1963    0.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7323   -1.8517   -2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294   -3.4740   -1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531   -3.5095   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -3.0413   -3.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -2.2945    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765   -2.2156   -0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080    0.5275    1.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3186    0.5471    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2047    2.5606    1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643    2.0212   -1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081    3.1988   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6243    1.5393   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  6
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 20 21  1  0
 21 22  1  0
 12  5  1  0
 27 15  1  0
 10  6  1  0
 18 11  1  0
 22  9  1  0
 24 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 12 36  1  0
 12 37  1  0
 15 38  1  1
 16 39  1  0
 16 40  1  0
 17 41  1  1
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  1
 23 50  1  0
 23 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  1
 28 55  1  0
 28 56  1  0
 28 57  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
M  CHG  2  24   1  25  -1
M  END


  Mrv1652309022213472D          

 28 33  0  0  1  0            999 V2000
    4.4096   -0.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505    0.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427    0.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939    0.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837    1.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525    2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460    2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289    3.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234    3.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0278    2.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    2.5492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3052    1.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    1.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    1.8785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7554    2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349    3.2175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7097    3.2842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5089    3.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    4.1388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4996    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729    4.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262    4.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    3.7295    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.2127    4.3279    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3410    3.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    2.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9297    1.8440    0.0000 C   0  0  0  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  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
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 20 23  1  1  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  CHG  2  24   1  25  -1
M  END
> <DATABASE_ID>
NP0154821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2CCC3=C2[C@@]2(C1)C(=O)[C@@H]1C[C@@H]4[C@@]2(C)[C@@H](C[N+]4([O-])CC1C)CC3

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO4/c1-12-10-24(27)11-14-6-4-13-5-7-15-17(21(26)28-3)9-23(19(13)15)20(25)16(12)8-18(24)22(14,23)2/h12,14,16,18H,4-11H2,1-3H3/t12?,14-,16-,18-,22-,23+,24?/m1/s1

> <INCHI_KEY>
KGESJSJJGMUDSQ-GMZBJENDSA-N

> <FORMULA>
C23H29NO4

> <MOLECULAR_WEIGHT>
383.488

> <EXACT_MASS>
383.209658418

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.903624517390405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,5R,10S)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1^{1,5}.0^{2,10}.0^{3,8}.0^{16,19}]icosa-13(19),16-dien-8-ium-8-olate

> <ALOGPS_LOGP>
0.60

> <JCHEM_LOGP>
1.6167375589999997

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.515427279176738

> <JCHEM_PKA_STRONGEST_BASIC>
3.725630023970852

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
105.93220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,5R,10S)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1^{1,5}.0^{2,10}.0^{3,8}.0^{16,19}]icosa-13(19),16-dien-8-ium-8-olate

> <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       8.231  -0.547   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.748   0.915   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.240   1.227   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.215   0.077   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.756   2.689   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.631   3.960   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.113   4.472   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.081   6.020   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.577   6.459   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.652   5.171   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.040   4.759   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.303   3.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.780   3.462   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.361   2.036   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.046   3.507   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.410   4.552   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.745   6.006   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.191   6.131   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.683   6.513   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.275   7.726   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.666   8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.109   7.939   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.729   8.214   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.663   6.962   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0      -0.397   8.079   0.000  0.00  0.00           O-1
HETATM   26  C   UNK     0      -0.636   5.968   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.460   4.305   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.735   3.442   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12   13   18                                             
CONECT   12   11    5                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   11   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21    9                                                       
CONECT   23   20   24                                                       
CONECT   24   23   17   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   15   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,3R,5R,10S)-2,6-dimethyl-8,20-dioxo-8-azahexacyclo[11.5.1.1,.0,.0,.0,]icosa-13(19),16-diene-17-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₉NO₄

Average Mass

383.4880 Da

Monoisotopic Mass

383.20966 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2CCC3=C2[C@@]2(C1)C(=O)[C@@H]1C[C@@H]4[C@@]2(C)[C@@H](C[N+]4([O-])CC1C)CC3

InChI Identifier

InChI=1S/C23H29NO4/c1-12-10-24(27)11-14-6-4-13-5-7-15-17(21(26)28-3)9-23(19(13)15)20(25)16(12)8-18(24)22(14,23)2/h12,14,16,18H,4-11H2,1-3H3/t12?,14-,16-,18-,22-,23+,24?/m1/s1

InChI Key

KGESJSJJGMUDSQ-GMZBJENDSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yuzurimine-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum that contain a 22 carbon core, commonly with a C9-C10 double bond, and C-22 is mostly a methyl ester of a carboxyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yuzurimine-type alkaloids

Sub Class

Not Available

Direct Parent

Yuzurimine-type alkaloids

Alternative Parents

Substituents

Yuzurimine-type alkaloid
Indolizidine
Indole or derivatives
N-alkylpyrrolidine
Piperidine
Trialkyl amine oxide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Ketone
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.6	ALOGPS
logS	-4.1	ALOGPS

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

137706291

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate (NP0154821)

MOL for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

3D MOL for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

3D SDF for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

3D-SDF for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

PDB for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

3D PDB for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

SMILES for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

INCHI for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

Structure for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)

3D Structure for NP0154821 ((1r,2s,3r,5r,10s)-17-(methoxycarbonyl)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.1¹,⁵.0²,¹⁰.0³,⁸.0¹⁶,¹⁹]icosa-13(19),16-dien-8-ium-8-olate)