NP-MRD: Showing NP-Card for (8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid (NP0163300)

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Record Information

Version

2.0

Created at

2022-09-02 21:53:29 UTC

Updated at

2022-09-02 21:53:29 UTC

NP-MRD ID

NP0163300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid

Description

Racemulosine belongs to the class of organic compounds known as quinolidines. These are organic compounds containing a quinolidine or decahydroquinoline moiety, which is a bicyclic skeleton consisting of a piperidine fused to a cyclohexane ring. (8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid is found in Aconitum racemulosum. (8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid was first documented in 2020 (PMID: 32888673). Based on a literature review very few articles have been published on Racemulosine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022223532D          

 28 33  0  0  1  0            999 V2000
    0.1067    1.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1621    0.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.0987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3777    0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1994    0.4265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8368    0.9503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7019    1.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8728    0.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6649   -0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8964   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -1.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433   -1.4160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4094   -2.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444   -1.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327   -1.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5767   -0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933   -1.6596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206   -2.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012   -0.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571   -0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512    0.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2278    0.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    1.3067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9303    1.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
  3 18  1  0  0  0  0
 16 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
  3 23  1  0  0  0  0
 14 24  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END

     RDKit          3D

 62 67  0  0  0  0  0  0  0  0999 V2000
    5.3714    0.9489   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4044    0.2035   -0.0171 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4383   -0.1166    0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6721   -1.1507    1.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    0.5437    0.7672 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8811    1.4940   -0.3686 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7308    0.8044   -1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5760   -0.6731   -1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986   -1.1912   -0.4770 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4211   -2.4159   -0.1079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677   -1.5309   -0.7316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3361   -0.7948   -1.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234    0.4528   -1.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3526    0.3280   -1.0004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9315    0.5748   -2.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333    1.6258   -2.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185    1.4204   -0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5144    1.1227    1.0342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0086    2.3841    1.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    2.7523    2.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572    0.3714    0.3138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4973   -1.1395    0.4925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7682   -1.6879    0.2558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667   -2.9363    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989   -2.7746    1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -0.9558   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    0.8155    0.7259 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4878    1.9925    0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -0.3098    0.7268 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8171   -0.9101    2.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0714    1.1557    1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816    2.3393   -0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671    1.3069   -2.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    1.0743   -2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1647   -1.0145   -2.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6122   -1.1262   -1.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412   -3.0103   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883   -2.6318   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -1.4458   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065   -0.5422   -2.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842    1.3753   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7260   -0.2162   -3.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502    2.4181   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0108    1.6910   -3.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5336    2.4216   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5857    1.2701    0.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    0.6233    1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6919    2.0471    3.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2401    2.8951    2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602    3.7424    2.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -1.4683    1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215   -3.4113    1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807   -3.6886    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7142   -1.8310    2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8230   -3.5985    2.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270   -2.6988    1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267   -1.5848   -1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076   -0.7735    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8139    1.0636    1.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186    2.8330    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335    2.4403   -0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812   -0.9031    1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 26  1  0
 26 14  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 18  1  1
 21 27  1  0
 27 28  1  0
 28  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
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 11 12  1  0
 12 13  1  0
 11 22  1  0
  9 29  1  0
 29  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
 14 15  1  6
 15 16  2  3
 22 23  1  0
 13 14  1  0
 13 21  1  0
 22 21  1  0
 29 27  1  0
  5  6  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 24 52  1  0
 24 53  1  0
 26 57  1  0
 26 58  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 20 48  1  0
 20 49  1  0
 20 50  1  0
 27 59  1  1
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 28 61  1  0
  6 32  1  6
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  7 34  1  0
  8 35  1  0
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 10 37  1  0
 11 38  1  6
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 22 51  1  1
 29 62  1  1
  5 31  1  1
  4 30  1  0
  2  1  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
M  END


  Mrv1652309022223532D          

 28 33  0  0  1  0            999 V2000
    0.1067    1.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1621    0.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.0987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3777    0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1994    0.4265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8368    0.9503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7019    1.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8728    0.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6649   -0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8964   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -1.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433   -1.4160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4094   -2.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444   -1.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327   -1.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5767   -0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909   -1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933   -1.6596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206   -2.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012   -0.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571   -0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512    0.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2278    0.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    1.3067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9303    1.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
  3 18  1  0  0  0  0
 16 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
  3 23  1  0  0  0  0
 14 24  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C[C@H](OC)C34C5CC6CC[C@](O)(C(CC23)C14)C5C6C(O)=N)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H34N2O3/c1-4-21-10-16(28-3)23-13-8-12-6-7-22(27,18(13)17(12)20(24)26)14(9-15(21)23)19(23)25(5-2)11-21/h4,12-19,27H,1,5-11H2,2-3H3,(H2,24,26)/t12?,13?,14?,15?,16-,17?,18?,19?,21+,22-,23?/m0/s1

> <INCHI_KEY>
BSOROLZKYXGRJC-LVXXQJFHSA-N

> <FORMULA>
C23H34N2O3

> <MOLECULAR_WEIGHT>
386.536

> <EXACT_MASS>
386.256942963

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.45769671167275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,13R,15S)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,16}]octadecane-4-carboximidic acid

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
-1.3424882644894716

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.31913019648789

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.4193998943222521

> <JCHEM_PKA_STRONGEST_BASIC>
13.08590281524063

> <JCHEM_POLAR_SURFACE_AREA>
76.78

> <JCHEM_REFRACTIVITY>
117.78229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8R,13R,15S)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,16}]octadecane-4-carboximidic acid

> <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       0.199   2.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.303   0.494   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.685  -0.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.572   1.208   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.106   0.796   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.295   1.774   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.044   3.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.216  -0.854   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.763  -0.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.229   0.875   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.708  -0.510   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.140  -2.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.916  -3.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.428  -2.643   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.364  -4.182   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.750  -3.063   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.861  -2.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.943  -0.781   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.716  -2.700   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.041  -3.098   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.484  -4.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.038  -4.769   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.122  -1.747   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.640  -1.106   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.936   0.168   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.892   1.707   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.537   2.439   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0       9.203   2.515   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18   23                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   18   19                                             
CONECT    9    8   10   24                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   24                                             
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17    8    3                                                  
CONECT   19   16    8   20                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20    3                                                       
CONECT   24   14    9   25                                                  
CONECT   25   24   11   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₄N₂O₃

Average Mass

386.5360 Da

Monoisotopic Mass

386.25694 Da

IUPAC Name

(8R,13R,15S)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,16}]octadecane-4-carboximidic acid

Traditional Name

(8R,13R,15S)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,16}]octadecane-4-carboximidic acid

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C[C@H](OC)C34C5CC6CC[C@](O)(C(CC23)C14)C5C6C(O)=N)C=C

InChI Identifier

InChI=1S/C23H34N2O3/c1-4-21-10-16(28-3)23-13-8-12-6-7-22(27,18(13)17(12)20(24)26)14(9-15(21)23)19(23)25(5-2)11-21/h4,12-19,27H,1,5-11H2,2-3H3,(H2,24,26)/t12?,13?,14?,15?,16-,17?,18?,19?,21+,22-,23?/m0/s1

InChI Key

BSOROLZKYXGRJC-LVXXQJFHSA-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
Aconitum racemulosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolidines. These are organic compounds containing a quinolidine or decahydroquinoline moiety, which is a bicyclic skeleton consisting of a piperidine fused to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolidines

Sub Class

Not Available

Direct Parent

Quinolidines

Alternative Parents

Substituents

Quinolidine
Azepane
Piperidine
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Dialkyl ether
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	1.1	ALOGPS
logP	-1.3	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	-0.42	ChemAxon
pKa (Strongest Basic)	13.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	76.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.78 m³·mol⁻¹	ChemAxon
Polarizability	43.46 Å³	ChemAxon
Number of Rings	6	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

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

132539864

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang S, Zhang JF, Chen L, Gao F, Zhou XL: Diterpenoid alkaloids from Aconitum anthoroideum that offer protection against MPP(+)-Induced apoptosis of SH-SY5Y cells and acetylcholinesterase inhibitory activity. Phytochemistry. 2020 Oct;178:112459. doi: 10.1016/j.phytochem.2020.112459. Epub 2020 Jul 23. [PubMed:32888673 ]
LOTUS database [Link]

Showing NP-Card for (8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid (NP0163300)

MOL for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

3D MOL for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

3D SDF for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

3D-SDF for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

PDB for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

3D PDB for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

SMILES for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

INCHI for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

Structure for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)

3D Structure for NP0163300 ((8r,13r,15s)-13-ethenyl-11-ethyl-8-hydroxy-15-methoxy-11-azahexacyclo[7.6.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁶]octadecane-4-carboximidic acid)