NP-MRD: Showing NP-Card for (1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one (NP0294199)

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Record Information

Version

2.0

Created at

2022-09-10 02:37:36 UTC

Updated at

2022-09-10 02:37:36 UTC

NP-MRD ID

NP0294199

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one

Description

Songoramine 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,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one is found in Aconitum barbatum, Aconitum carmichaelii, Aconitum monticola and Aconitum napellus. (1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one was first documented in 2011 (PMID: 20862641). Based on a literature review a small amount of articles have been published on Songoramine (PMID: 33995019) (PMID: 35948501) (PMID: 35924046).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102204372D          

 26 32  0  0  1  0            999 V2000
    4.5626    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7797    2.0179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1391    1.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4563    1.4305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8861    0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3440    0.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.8032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0266    1.8377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3174    2.3473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5665    1.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    1.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    0.6655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1532   -0.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715    1.4177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3702    2.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3626    1.8425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3603    2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0737    3.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    1.3693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9561    2.1516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4909    2.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655    2.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8207    3.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0595    0.7807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8937   -0.0274    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
  8  7  1  6  0  0  0
  9  8  1  1  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
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 17  1  1  0  0  0
  6 20  1  0  0  0  0
  9 20  1  0  0  0  0
  9 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  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

 55 61  0  0  0  0  0  0  0  0999 V2000
    0.4635   -7.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271   -5.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1568   -5.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135   -2.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -1.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000   -2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500   -3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135   -2.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -3.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7406   -4.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0264   -5.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817   -4.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964   -3.8171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402   -8.5757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9307   -7.7728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -7.2010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204   -5.3596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -6.4235    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7099   -2.8302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4734   -0.3511    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5984   -0.4319    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -3.8971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861    1.3808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095    0.5130    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    1.4979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0080   -2.1160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8991   -0.3349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6528   -5.0950    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1308   -3.3111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6710   -4.9392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828   -1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115   -1.6365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -1.5935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0104   -3.7993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4443   -2.1071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964   -5.8245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230   -4.2807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 20  1  0
 20  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23  3  1  0
  3  4  1  0
  4  5  1  0
  5 25  1  0
 25 26  1  0
 25  2  1  0
  2  1  2  3
  9 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  0
  9 20  1  0
  5 21  1  0
 16 10  1  0
  5  6  1  1
 13  8  1  0
  2  3  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 18 45  1  0
 18 46  1  0
 20 50  1  1
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  1
 21 51  1  6
 22 52  1  0
 22 53  1  0
  3 29  1  6
  4 30  1  0
  4 31  1  0
 25 54  1  1
 26 55  1  0
  1 27  1  0
  1 28  1  0
 10 36  1  1
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  1
M  END


  Mrv1652309102204372D          

 26 32  0  0  1  0            999 V2000
    4.5626    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7797    2.0179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1391    1.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4563    1.4305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8861    0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3440    0.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.8032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0266    1.8377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3174    2.3473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5665    1.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    1.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    0.6655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1532   -0.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715    1.4177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3702    2.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3626    1.8425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3603    2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0737    3.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1906    1.3693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9561    2.1516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4909    2.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655    2.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8207    3.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0595    0.7807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8937   -0.0274    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
  8  7  1  6  0  0  0
  9  8  1  1  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
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 17  1  1  0  0  0
  6 20  1  0  0  0  0
  9 20  1  0  0  0  0
  9 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  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>
NP0294199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1[C@@H]2C3C[C@H]4[C@]2([C@@H]2CC(=O)[C@H]5C[C@]32[C@H](O)C5=C)[C@@H]2CC[C@@]4(C)[C@@H]1O2

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO3/c1-4-23-17-12-7-14-20(3)6-5-16(26-19(20)23)22(14,17)15-8-13(24)11-9-21(12,15)18(25)10(11)2/h11-12,14-19,25H,2,4-9H2,1,3H3/t11-,12?,14+,15+,16-,17+,18+,19-,20+,21-,22-/m0/s1

> <INCHI_KEY>
YSSPOBAEOOLGAT-LSWXXAQXSA-N

> <FORMULA>
C22H29NO3

> <MOLECULAR_WEIGHT>
355.478

> <EXACT_MASS>
355.214743798

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
88.4437102883045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,5R,8S,10S,12R,13S,14R,17S,19R)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0^{1,14}.0^{2,12}.0^{4,13}.0^{5,10}.0^{8,13}]icosan-16-one

> <JCHEM_LOGP>
1.7138801713333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.437509136898303

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.679533203362794

> <JCHEM_PKA_STRONGEST_BASIC>
5.663771287769157

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
96.28319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,8S,10S,12R,13S,14R,17S,19R)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0^{1,14}.0^{2,12}.0^{4,13}.0^{5,10}.0^{8,13}]icosan-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.517   1.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.192   2.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.056   3.767   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.860   3.327   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.585   2.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.521   1.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.509   0.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.385   1.499   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.916   3.430   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.592   4.382   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.058   3.532   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.408   1.917   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.064   1.242   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.286  -0.282   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.693   2.646   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.691   4.368   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       0.677   3.439   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.673   4.979   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.004   5.753   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.222   2.556   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.651   4.016   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.650   5.364   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.282   5.221   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.132   6.506   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.711   1.457   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.402  -0.051   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21   25                                             
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   20   21                                             
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15   10                                                       
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    6    9                                                  
CONECT   21    9    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
CONECT   25    5    2   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉NO₃

Average Mass

355.4780 Da

Monoisotopic Mass

355.21474 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1[C@@H]2C3C[C@H]4[C@]2([C@@H]2CC(=O)[C@H]5C[C@]32[C@H](O)C5=C)[C@@H]2CC[C@@]4(C)[C@@H]1O2

InChI Identifier

InChI=1S/C22H29NO3/c1-4-23-17-12-7-14-20(3)6-5-16(26-19(20)23)22(14,17)15-8-13(24)11-9-21(12,15)18(25)10(11)2/h11-12,14-19,25H,2,4-9H2,1,3H3/t11-,12?,14+,15+,16-,17+,18+,19-,20+,21-,22-/m0/s1

InChI Key

YSSPOBAEOOLGAT-LSWXXAQXSA-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 barbatum	LOTUS Database	35616633
Aconitum carmichaelii	LOTUS Database	35616633
Aconitum monticola	LOTUS Database	35616633
Aconitum napellus	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
Naphthopyran
Naphthalene
Azepane
1,3-oxazinane
Oxane
Oxazinane
Piperidine
Pyran
Cyclic alcohol
Hemiaminal
Ketone
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
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

C00024814

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

134715137

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ye X, Wu J, Zhang D, Lan Z, Yang S, Zhu J, Yang M, Gong Q, Zhong L: How Aconiti Radix Cocta can Treat Gouty Arthritis Based on Systematic Pharmacology and UPLC-QTOF-MS/MS. Front Pharmacol. 2021 Apr 30;12:618844. doi: 10.3389/fphar.2021.618844. eCollection 2021. [PubMed:33995019 ]
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 ]
Forgo P, Borcsa B, Csupor D, Fodor L, Berkecz R, Molnar V A, Hohmann J: Diterpene alkaloids from Aconitum anthora and assessment of the hERG-inhibiting ability of Aconitum alkaloids. Planta Med. 2011 Mar;77(4):368-73. doi: 10.1055/s-0030-1250362. Epub 2010 Sep 22. [PubMed:20862641 ]
He Q, Tan X, Geng S, Du Q, Pei Z, Zhang Y, Wang S, Zhang Y: Network analysis combined with pharmacological evaluation strategy to reveal the mechanism of Tibetan medicine Wuwei Shexiang pills in treating rheumatoid arthritis. Front Pharmacol. 2022 Jul 18;13:941013. doi: 10.3389/fphar.2022.941013. eCollection 2022. [PubMed:35924046 ]
LOTUS database [Link]

Showing NP-Card for (1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one (NP0294199)

MOL for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

3D MOL for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

3D SDF for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

3D-SDF for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

PDB for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

3D PDB for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

SMILES for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

INCHI for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

Structure for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)

3D Structure for NP0294199 ((1r,4s,5r,8s,10s,12r,13s,14r,17s,19r)-11-ethyl-19-hydroxy-5-methyl-18-methylidene-9-oxa-11-azaheptacyclo[15.2.1.0¹,¹⁴.0²,¹².0⁴,¹³.0⁵,¹⁰.0⁸,¹³]icosan-16-one)