NP-MRD: Showing NP-Card for (1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate (NP0149036)

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Record Information

Version

2.0

Created at

2022-09-02 04:51:54 UTC

Updated at

2022-09-02 04:51:54 UTC

NP-MRD ID

NP0149036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate

Description

Napelline N-oxide belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate is found in Aconitum karakolicum. (1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate was first documented in 2012 (PMID: 22803106). Based on a literature review a small amount of articles have been published on Napelline N-oxide (PMID: 25110090) (PMID: 24770754).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206512D          

 27 32  0  0  1  0            999 V2000
    4.8871    0.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1006    1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891    2.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3711    1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6967    1.4648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0949    0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428    0.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274    0.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2307    0.6140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2681   -0.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    1.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292    2.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    2.1843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4901    3.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073    1.7833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1833    2.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    2.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    2.8864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0409    3.5695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540    1.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691    1.6730    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.0197    2.4179    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.5383    2.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4421    2.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    0.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    0.8568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4705    0.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  4  1  1  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  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15  8  1  1  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  6  0  0  0
 15 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
  9 25  1  0  0  0  0
  5 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  CHG  2  21   1  22  -1
M  END

     RDKit          2D

 60 65  0  0  0  0  0  0  0  0999 V2000
   -1.9206   -5.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9206   -4.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424   -3.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -1.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1328    3.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086    3.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351    3.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470    1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    0.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9140   -0.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -0.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0159   -1.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2594   -1.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8520    0.5062    0.0000 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3551    1.1246    0.0000 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9468   -0.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0415   -1.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1740    1.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -4.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2197   -6.3358    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216   -6.3358    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7443   -4.5745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3818   -4.5246    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -3.7516    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0283   -2.5730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004    0.7041    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -1.0037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8615    1.5254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5593    3.6078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8466    4.6167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277    1.8722    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    5.0089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    4.7451    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    3.2733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    4.7063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    2.3156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3838    0.8952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1861    0.3312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785    0.6653    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612   -0.2574    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9185   -3.1886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6076   -1.8094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293   -1.7730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -1.7308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9722    0.5755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2531   -2.4290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9259   -0.3331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3115   -2.8550    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721    1.9193    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602    3.3326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273   -2.7656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429   -4.5032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 25  1  0
 25  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15  8  1  0
  8  7  1  0
  7  6  1  0
  6 20  1  0
  5  6  1  6
  5  4  1  0
  4  3  1  0
  3 18  1  0
 18 19  1  0
 18 17  1  0
 17 16  1  0
  3  2  1  0
  2  1  2  3
  2 26  1  0
 26 27  1  0
 20 21  1  0
 16  5  1  0
  8  9  1  0
 26  5  1  0
 20 15  1  0
 15 16  1  6
 24 54  1  0
 24 55  1  0
 24 56  1  0
 23 52  1  0
 23 53  1  0
 25 57  1  0
 25 58  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  6
 14 45  1  0
  8 36  1  0
  7 34  1  0
  7 35  1  0
  6 33  1  0
 20 51  1  0
  4 31  1  0
  4 32  1  0
  3 30  1  1
 18 49  1  6
 19 50  1  0
 17 47  1  0
 17 48  1  0
 16 46  1  0
  1 28  1  0
  1 29  1  0
 26 59  1  1
 27 60  1  0
M  CHG  2  21   1  22  -1
M  END


  Mrv1652309022206512D          

 27 32  0  0  1  0            999 V2000
    4.8871    0.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1006    1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891    2.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3711    1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6967    1.4648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0949    0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428    0.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274    0.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2307    0.6140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2681   -0.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    1.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292    2.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    2.1843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4901    3.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073    1.7833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1833    2.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    2.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    2.8864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0409    3.5695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540    1.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691    1.6730    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.0197    2.4179    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.5383    2.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4421    2.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    0.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    0.8568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4705    0.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  4  1  1  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  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15  8  1  1  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  6  0  0  0
 15 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
  9 25  1  0  0  0  0
  5 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  CHG  2  21   1  22  -1
M  END
> <DATABASE_ID>
NP0149036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[N+]1([O-])C[C@]2(C)CC[C@H](O)[C@@]34C2CC(C13)[C@]12C[C@@H]([C@@H](O)CC41)C(=C)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO4/c1-4-23(27)10-20(3)6-5-17(25)22-15(20)7-13(18(22)23)21-9-12(11(2)19(21)26)14(24)8-16(21)22/h12-19,24-26H,2,4-10H2,1,3H3/t12-,13?,14+,15?,16?,17+,18?,19-,20+,21-,22+,23?/m1/s1

> <INCHI_KEY>
DEMQJEXKIJFBRD-LGTBQFFLSA-N

> <FORMULA>
C22H33NO4

> <MOLECULAR_WEIGHT>
375.509

> <EXACT_MASS>
375.240958547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
13.42837234528216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,5R,7R,8S,13R,16S)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-11-ium-11-olate

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-0.5934888963333322

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.495625884476446

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.91436548931296

> <JCHEM_PKA_STRONGEST_BASIC>
3.7229707693832346

> <JCHEM_POLAR_SURFACE_AREA>
83.75

> <JCHEM_REFRACTIVITY>
101.73349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,7R,8S,13R,16S)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-11-ium-11-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       9.123   1.715   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.654   2.333   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.446   3.983   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.293   3.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.034   2.734   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.911   1.635   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.066   0.396   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.918   1.371   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.431   1.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.500  -0.491   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.595   2.707   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.055   4.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.867   4.077   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.915   5.823   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.440   3.329   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.076   4.041   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.936   5.433   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.576   5.388   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.543   6.663   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.341   2.412   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       0.689   3.123   0.000  0.00  0.00           N+1
HETATM   22  O   UNK     0       1.903   4.513   0.000  0.00  0.00           O-1
HETATM   23  C   UNK     0      -1.005   3.993   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.692   3.889   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.465   1.846   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.204   1.599   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.478   0.018   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16   26                                             
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11   25                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16   20                                             
CONECT   16   15    5   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    3   19                                                  
CONECT   19   18                                                            
CONECT   20   15    6   21                                                  
CONECT   21   20   22   23   25                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   21    9                                                       
CONECT   26    5    2   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₄

Average Mass

375.5090 Da

Monoisotopic Mass

375.24096 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[N+]1([O-])C[C@]2(C)CC[C@H](O)[C@@]34C2CC(C13)[C@]12C[C@@H]([C@@H](O)CC41)C(=C)[C@H]2O

InChI Identifier

InChI=1S/C22H33NO4/c1-4-23(27)10-20(3)6-5-17(25)22-15(20)7-13(18(22)23)21-9-12(11(2)19(21)26)14(24)8-16(21)22/h12-19,24-26H,2,4-10H2,1,3H3/t12-,13?,14+,15?,16?,17+,18?,19-,20+,21-,22+,23?/m1/s1

InChI Key

DEMQJEXKIJFBRD-LGTBQFFLSA-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 karakolicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Azepane
Piperidine
Trialkyl amine oxide
Cyclic alcohol
Secondary alcohol
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Polyol
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
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	-0.01	ALOGPS
logS	-2.9	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024805

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

139291820

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nesterova YV, Povet'yeva TN, Suslov NI, Zyuz'kov GN, Pushkarskii SV, Aksinenko SG, Schultz EE, Kravtsova SS, Krapivin AV: Analgesic activity of diterpene alkaloids from Aconitum baikalensis. Bull Exp Biol Med. 2014 Aug;157(4):488-91. doi: 10.1007/s10517-014-2598-6. Epub 2014 Aug 12. [PubMed:25110090 ]
Nesterova YV, Povetieva TN, Suslov NI, Zyuz'kov GN, Aksinenko SG, Pushkarskii SV, Krapivin AV: Anti-inflammatory activity of diterpene alkaloids from Aconitum baikalense. Bull Exp Biol Med. 2014 Mar;156(5):665-8. doi: 10.1007/s10517-014-2421-4. Epub 2014 Mar 30. [PubMed:24770754 ]
Nesterova YV, Povetieva TN, Suslov NI, Zhdanov VV, Hrichkova TY, Udut EV, Chaykovskiy AS, Gaydamovich NN, Andreeva TI, Dygai AM: Regeneratory characteristics of complex extract and isolated diterpene alkaloids of Aconitum baikalense. Bull Exp Biol Med. 2012 Feb;152(4):439-43. doi: 10.1007/s10517-012-1548-4. [PubMed:22803106 ]
LOTUS database [Link]

Showing NP-Card for (1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate (NP0149036)

MOL for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

3D MOL for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

3D SDF for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

3D-SDF for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

PDB for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

3D PDB for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

SMILES for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

INCHI for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

Structure for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)

3D Structure for NP0149036 ((1r,4s,5r,7r,8s,13r,16s)-11-ethyl-4,7,16-trihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-11-ium-11-olate)