NP-MRD: Showing NP-Card for (1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one (NP0190620)

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Record Information

Version

2.0

Created at

2022-09-04 07:19:32 UTC

Updated at

2022-09-04 07:19:32 UTC

NP-MRD ID

NP0190620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one

Description

Songorine belongs to the class of organic compounds known as napelline-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the napelline skeleton, which is a hexacyclic compound, with an additional C-20-C-7 bond in the kaurane-type. (1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one is found in Aconitum baicalense, Aconitum barbatum, Aconitum carmichaelii, Aconitum episcopale, Aconitum ferox, Aconitum firmum, Aconitum karakolicum, Aconitum kusnezoffii, Aconitum liangshanicum, Aconitum monticola, Aconitum napellus, Aconitum nemorum, Aconitum septentrionale and Aconitum soongaricum. (1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one was first documented in 2021 (PMID: 33791002). Based on a literature review a small amount of articles have been published on Songorine (PMID: 35662724) (PMID: 35948501) (PMID: 36062176) (PMID: 33460195).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209192D          

 26 31  0  0  1  0            999 V2000
    5.2681   -0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017    0.6615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4651    0.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -0.4634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4549    0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086    1.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4216    1.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509    2.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130   -0.3548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6459    0.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    1.1454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -0.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664   -0.4832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1758   -1.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3991   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884   -1.3327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5271   -1.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993   -1.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3721   -1.1329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4663   -1.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0350   -0.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9017   -0.7454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1345   -1.5369    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  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  6  1  1  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 10 24  1  0  0  0  0
  5 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END

     RDKit          2D

 57 62  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
   -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
   -5.5076   -2.1474    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
   -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
   -1.8351    3.2209    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
    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
   -1.1740    1.8442    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  0  0  0  0  0  0  0
   -3.3498    0.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476    0.3425    0.0000 C   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
    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
   -0.7071   -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
   -3.0798    0.4804    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   -0.9834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4589    2.4809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3226    1.0678    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
   -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
    3.5593    3.6078    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
    1.8466    4.6167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518    2.1014    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
   -3.6328   -1.0487    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7916    1.8578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3453    0.2607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489   -1.1541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294    1.8403    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -1.6317    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
    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
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 10 11  1  1
 10 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 22  5  1  0
  5  4  1  1
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 25  1  0
 25 26  1  0
  3  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
 21 18  1  0
 25  5  1  0
 24 15  1  0
  6  5  1  0
 21 10  1  0
  6 10  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 19 46  1  0
 19 47  1  0
 17 44  1  0
 17 45  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 14 39  1  0
 14 40  1  0
 13 37  1  0
 13 38  1  0
 11 35  1  0
 12 36  1  0
 24 55  1  0
 23 53  1  0
 23 54  1  0
 22 52  1  1
 21 51  1  0
  4 30  1  0
  4 31  1  0
  3 29  1  6
  1 27  1  0
  1 28  1  0
 25 56  1  1
 26 57  1  0
  7 33  1  0
  7 34  1  0
  6 32  1  0
M  END


  Mrv1652309042209192D          

 26 31  0  0  1  0            999 V2000
    5.2681   -0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017    0.6615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4651    0.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -0.4634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4549    0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086    1.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4216    1.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509    2.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130   -0.3548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6459    0.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    1.1454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -0.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664   -0.4832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1758   -1.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3991   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884   -1.3327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5271   -1.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993   -1.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3721   -1.1329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4663   -1.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0350   -0.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9017   -0.7454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1345   -1.5369    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  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  6  1  1  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 10 24  1  0  0  0  0
  5 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0190620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)CCC(O)[C@@]34C2C[C@@H](C13)[C@]12C[C@@H](C(=C)[C@H]1O)C(=O)CC42

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO3/c1-4-23-10-20(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/h12-13,15-19,25-26H,2,4-10H2,1,3H3/t12-,13-,15?,16?,17?,18?,19+,20-,21-,22-/m0/s1

> <INCHI_KEY>
CBOSLVQFGANWTL-VTXPNNKDSA-N

> <FORMULA>
C22H31NO3

> <MOLECULAR_WEIGHT>
357.494

> <EXACT_MASS>
357.230393862

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
32.31508190881372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,7R,8R,9R,13R)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-4-one

> <JCHEM_LOGP>
0.9164005406666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.60407977105563

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.549812198075081

> <JCHEM_PKA_STRONGEST_BASIC>
9.25465854689705

> <JCHEM_POLAR_SURFACE_AREA>
60.769999999999996

> <JCHEM_REFRACTIVITY>
98.76339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,7R,8R,9R,13R)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.834  -0.226   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.297  -0.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.470   1.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.468   0.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.711  -0.865   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.582   0.340   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.869   2.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.387   2.416   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.815   3.895   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.384  -0.662   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.072   1.048   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.161   2.138   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.564   1.322   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.930  -0.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.551  -0.902   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.195  -2.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.478  -0.920   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.205  -2.488   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       6.584  -3.174   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.679  -4.711   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.732  -2.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.428  -2.115   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.737  -3.089   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.932  -1.807   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.283  -1.391   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.718  -2.869   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22   25                                             
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11   21   24                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   24                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   10   22                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   15   10                                                  
CONECT   25    5    2   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO₃

Average Mass

357.4940 Da

Monoisotopic Mass

357.23039 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C)CCC(O)[C@@]34C2C[C@@H](C13)[C@]12C[C@@H](C(=C)[C@H]1O)C(=O)CC42

InChI Identifier

InChI=1S/C22H31NO3/c1-4-23-10-20(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/h12-13,15-19,25-26H,2,4-10H2,1,3H3/t12-,13-,15?,16?,17?,18?,19+,20-,21-,22-/m0/s1

InChI Key

CBOSLVQFGANWTL-VTXPNNKDSA-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 baicalense	LOTUS Database	35616633
Aconitum barbatum	LOTUS Database	35616633
Aconitum carmichaelii	LOTUS Database	35616633
Aconitum episcopale	LOTUS Database	35616633
Aconitum ferox	LOTUS Database	35616633
Aconitum firmum	LOTUS Database	35616633
Aconitum karakolicum	LOTUS Database	35616633
Aconitum kusnezoffii	LOTUS Database	35616633
Aconitum liangshanicum	LOTUS Database	35616633
Aconitum monticola	LOTUS Database	35616633
Aconitum napellus	LOTUS Database	35616633
Aconitum nemorum	LOTUS Database	35616633
Aconitum septentrionale	LOTUS Database	35616633
Aconitum soongaricum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as napelline-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the napelline skeleton, which is a hexacyclic compound, with an additional C-20-C-7 bond in the kaurane-type.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Napelline-type diterpenoid alkaloids

Alternative Parents

Substituents

Napelline-type diterpenoid alkaloid
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024815

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

139291804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang L, Siyiti M, Zhang J, Yao M, Zhao F: Anti-inflammatory and anti-rheumatic activities in vitro of alkaloids separated from Aconitum soongoricum Stapf. Exp Ther Med. 2021 May;21(5):493. doi: 10.3892/etm.2021.9924. Epub 2021 Mar 17. [PubMed:33791002 ]
Chen ZY, Wei XY, Qiu ZD, Huang Y, Tan T, Feng YL, Guo J, Cui GH, Huang LQ, Lai CJ: Compatibility of Fuzi and Ginseng Significantly Increase the Exposure of Aconitines. Front Pharmacol. 2022 Apr 26;13:883898. doi: 10.3389/fphar.2022.883898. eCollection 2022. [PubMed:35662724 ]
Jin S, Zhao X, Ma D: Divergent Total Syntheses of Napelline-Type C20-Diterpenoid Alkaloids: (-)-Napelline, (+)-Dehydronapelline, (-)-Songorine, (-)-Songoramine, (-)-Acoapetaldine D, and (-)-Liangshanone. J Am Chem Soc. 2022 Aug 24;144(33):15355-15362. doi: 10.1021/jacs.2c06738. Epub 2022 Aug 10. [PubMed:35948501 ]
Yuan H, Liu Y, Huang K, Hao H, Xue YT: Therapeutic Mechanism and Key Active Ingredients of Shenfu Injection in Sepsis: A Network Pharmacology and Molecular Docking Approach. Evid Based Complement Alternat Med. 2022 Aug 26;2022:9686149. doi: 10.1155/2022/9686149. eCollection 2022. [PubMed:36062176 ]
Wang X, Lei H, Qi X, Guo X, Xu X, Zu X, Ye J: Simultaneous determination of five bioactive components of XiaoJin Capsule in normal and mammary gland hyperplasia rat plasma using LC-MS/MS and its application to a pharmacokinetic study. Biomed Chromatogr. 2021 Mar;35(3):e5000. doi: 10.1002/bmc.5000. Epub 2020 Oct 29. [PubMed:33460195 ]
LOTUS database [Link]

Showing NP-Card for (1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one (NP0190620)

MOL for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D MOL for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D SDF for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D-SDF for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

PDB for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D PDB for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

SMILES for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

INCHI for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

Structure for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)

3D Structure for NP0190620 ((1r,5s,7r,8r,9r,13r)-11-ethyl-7,16-dihydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-4-one)