NP-MRD: Showing NP-Card for (1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one (NP0316430)

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Record Information

Version

2.0

Created at

2022-09-11 15:37:29 UTC

Updated at

2022-09-11 15:37:29 UTC

NP-MRD ID

NP0316430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one

Description

Hetisinone belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. (1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one is found in Aconitum tanguticum, Delphinium delavayi, Delphinium fissum, Delphinium gracile, Delphinium occidentale, Delphinium peregrinum, Delphinium tatsienense, Delphinium venulosum and Delphinium virgatum. (1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one was first documented in 2011 (PMID: 20862641). Based on a literature review a small amount of articles have been published on Hetisinone (PMID: 24452459) (PMID: 28813032) (PMID: 28457693) (PMID: 29262708).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217372D          

 24 30  0  0  1  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.6350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9611    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940    0.6205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4176   -0.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0434   -0.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4083   -1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4804    0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    0.1461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0890   -0.6085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2832   -0.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6437   -0.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301   -0.4517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7342   -0.0353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7014    0.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.1655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8546   -0.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006   -1.0816    0.0000 C   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  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19  2  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 14  1  6  0  0  0
  4 22  1  0  0  0  0
 15 23  1  6  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
M  END

     RDKit          3D

 49 55  0  0  0  0  0  0  0  0999 V2000
    4.6716    1.0490   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275    0.6543   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9624   -0.7319   -0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4751   -0.7164   -0.3110 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8848   -2.0188   -0.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -1.9090   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3188   -1.3505    0.3273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6363   -0.8119   -0.1711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0908    0.5408   -0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4076   -1.2110    1.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7352   -0.2209    1.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3513    0.0782    2.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3634    0.3731    1.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5884   -0.0494    0.5940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6315    0.3087   -0.7935 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8900    0.3713   -1.1575 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4323    1.7352   -0.7971 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4260    2.6779   -0.6100 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3171    1.5882    0.4252 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5907    0.8132    1.5363 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9254    1.7208    2.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559   -0.3546    1.0235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0376   -0.7945   -1.6837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392   -1.2771   -1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9392    2.0674    0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424    0.3654   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -0.9936   -1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -1.4151    0.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634   -2.8582   -0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2960   -2.2357   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825   -2.8823   -1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2679   -2.0349    1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8657    1.4076    0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1686    0.9296   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2420    0.5048   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129   -2.2304    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4879   -0.9509    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283   -0.0467    2.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3653    1.4635    2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8918    1.3042   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0453    0.2272   -2.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851    2.1292   -1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    3.5893   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6957    2.5320    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362    0.4151    2.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835    2.5883    1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8849   -1.1766    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -2.3499   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928   -0.8141   -2.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8 24  1  0
 24 23  1  0
 23  6  1  0
  6  5  1  0
  4  5  1  6
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 19  1  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  1
 13 11  1  0
 11 12  2  0
 11 10  1  0
 14  7  1  0
 14 22  1  0
 22 20  1  0
 20 21  1  0
 10  8  1  0
  7  8  1  0
 15 23  1  0
  7  6  1  0
 16  4  1  0
 22  4  1  0
 20 19  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 24 48  1  0
 24 49  1  0
  6 31  1  6
  5 29  1  0
  5 30  1  0
  3 27  1  0
  3 28  1  0
  1 25  1  0
  1 26  1  0
 19 44  1  1
 17 42  1  6
 18 43  1  0
 16 41  1  6
 15 40  1  1
 13 38  1  0
 13 39  1  0
 10 36  1  0
 10 37  1  0
  7 32  1  1
 22 47  1  1
 20 45  1  1
 21 46  1  0
M  END


  Mrv1652309112217372D          

 24 30  0  0  1  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.6350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9611    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940    0.6205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4176   -0.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0434   -0.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4083   -1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4804    0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    0.1461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0890   -0.6085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2832   -0.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6437   -0.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301   -0.4517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7342   -0.0353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7014    0.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.1655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8546   -0.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006   -1.0816    0.0000 C   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  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19  2  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 14  1  6  0  0  0
  4 22  1  0  0  0  0
 15 23  1  6  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CN3[C@H]4C[C@@]56CC(=C)[C@H]7C(O)[C@@H]5[C@@H]3[C@@](CC(=O)C1)([C@@H]24)[C@@H]6[C@@H]7O

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO3/c1-8-3-19-6-10-15-18(2)4-9(22)5-20(15)16(19)14(24)11(8)13(23)12(19)17(20)21(10)7-18/h10-17,23-24H,1,3-7H2,2H3/t10-,11-,12+,13?,14+,15+,16+,17+,18+,19-,20-/m0/s1

> <INCHI_KEY>
WCGQPPIMPLNHFG-UVWZWZDJSA-N

> <FORMULA>
C20H25NO3

> <MOLECULAR_WEIGHT>
327.424

> <EXACT_MASS>
327.183443669

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
50.54976502586392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S,8R,9S,11R,14R,16S,17R,18R,19S)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-one

> <JCHEM_LOGP>
-0.7152637903333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.890601162949633

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.190683718845488

> <JCHEM_PKA_STRONGEST_BASIC>
8.378206761589313

> <JCHEM_POLAR_SURFACE_AREA>
60.77

> <JCHEM_REFRACTIVITY>
87.43050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,8R,9S,11R,14R,16S,17R,18R,19S)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.223   0.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.718   0.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.494   1.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.091   1.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.661   1.913   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.216   1.158   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.379  -0.088   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.548  -1.271   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.229  -2.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.002  -0.619   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.131   0.747   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.007   2.014   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.497   1.091   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.803   0.273   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.900  -1.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.395  -0.629   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.202  -1.746   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.302  -3.282   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.056  -0.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.370  -0.066   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.309   1.473   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.138   0.309   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       5.329  -0.655   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.161  -2.019   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16   22                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10   24                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15   22                                             
CONECT   15   14   16   23                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14    4                                                  
CONECT   23   15    6   24                                                  
CONECT   24   23    8                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₅NO₃

Average Mass

327.4240 Da

Monoisotopic Mass

327.18344 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12CN3[C@H]4C[C@@]56CC(=C)[C@H]7C(O)[C@@H]5[C@@H]3[C@@](CC(=O)C1)([C@@H]24)[C@@H]6[C@@H]7O

InChI Identifier

InChI=1S/C20H25NO3/c1-8-3-19-6-10-15-18(2)4-9(22)5-20(15)16(19)14(24)11(8)13(23)12(19)17(20)21(10)7-18/h10-17,23-24H,1,3-7H2,2H3/t10-,11-,12+,13?,14+,15+,16+,17+,18+,19-,20-/m0/s1

InChI Key

WCGQPPIMPLNHFG-UVWZWZDJSA-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 tanguticum	LOTUS Database	35616633
Delphinium delavayi	LOTUS Database	35616633
Delphinium fissum	LOTUS Database	35616633
Delphinium gracile	LOTUS Database	35616633
Delphinium occidentale	LOTUS Database	35616633
Delphinium peregrinum	LOTUS Database	35616633
Delphinium tatsienense	LOTUS Database	35616633
Delphinium venulosum	LOTUS Database	35616633
Delphinium virgatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Azaspirodecane
Isoindolone
Quinolizidine
Indole or derivatives
Indolizidine
Isoindoline
Alkaloid or derivatives
Isoindole or derivatives
Azepane
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Ketone
Cyclic ketone
Azacycle
Organoheterocyclic compound
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
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

C00024824

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

101930090

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Borcsa B, Fodor L, Csupor D, Forgo P, Molnar A 5th, Hohmann J: Diterpene alkaloids from the roots of Aconitum moldavicum and assessment of Nav 1.2 sodium channel activity of aconitum alkaloids. Planta Med. 2014 Feb;80(2-3):231-6. doi: 10.1055/s-0033-1360278. Epub 2014 Jan 22. [PubMed:24452459 ]
Mericl F, Mericli AH, Desai HK, Ulubelen A, Pelletier SW: Diterpenoid Alkaloids from Consolida regalis S. F.Gray subsp.paniculata (Host) Soo var. paniculata. Sci Pharm. 2017 Aug 16;69(1):61-65. doi: 10.3797/scipharm.aut-01-07. [PubMed:28813032 ]
Ahmad H, Ahmad S, Shah SAA, Latif A, Ali M, Khan FA, Tahir MN, Shaheen F, Wadood A, Ahmad M: Antioxidant and anticholinesterase potential of diterpenoid alkaloids from Aconitum heterophyllum. Bioorg Med Chem. 2017 Jul 1;25(13):3368-3376. doi: 10.1016/j.bmc.2017.04.022. Epub 2017 Apr 19. [PubMed:28457693 ]
Kiss T, Macsai L, Csupor D, Datki ZL: In vivo screening of diterpene alkaloids using bdelloid rotifer assays. Acta Biol Hung. 2017 Dec;68(4):443-452. doi: 10.1556/018.68.2017.4.9. [PubMed:29262708 ]
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 ]
LOTUS database [Link]

Showing NP-Card for (1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one (NP0316430)

MOL for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D MOL for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D SDF for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D-SDF for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

PDB for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D PDB for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

SMILES for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

INCHI for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

Structure for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D Structure for NP0316430 ((1s,5s,8r,9s,11r,14r,16s,17r,18r,19s)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)