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Showing NP-Card for (-)-Liangshanone (NP0067218)

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Record Information
Version2.0
Created at2022-04-28 11:37:29 UTC
Updated at2022-04-28 11:37:29 UTC
NP-MRD IDNP0067218
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Liangshanone
Description(1S,2R,5R,7R,8S,9S,10S,13S,16S,17R)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]Nonadecan-4-one 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. (-)-Liangshanone is found in Aconitum liangshanicum and Aconitum liangshanium. Based on a literature review very few articles have been published on (1S,2R,5R,7R,8S,9S,10S,13S,16S,17R)-11-ethyl-7-hydroxy-16-methoxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]Nonadecan-4-one.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0067218 ((-)-Liangshanone)


  Mrv1652304282213372D          

 27 32  0  0  1  0            999 V2000
    1.5711    1.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8428    0.8241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167    0.5350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4023    0.5605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3177   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572   -0.8670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7032   -0.8169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8774    0.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201    0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2521   -0.4780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4537   -0.3475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2936   -0.7832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9167   -0.0794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4168   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9861   -1.0354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4313   -1.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7360   -2.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849   -1.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3482   -0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567   -0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7068    0.3471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8086    1.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7888   -1.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -1.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -1.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607    1.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  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  0  0  0  0
 10 11  1  0  0  0  0
 11  3  1  1  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  1  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
 10 23  1  1  0  0  0
 23 24  1  0  0  0  0
  7 25  1  6  0  0  0
  7 26  1  0  0  0  0
  2 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
Download

3D MOL for NP0067218 ((-)-Liangshanone)

Download
3D SDF for NP0067218 ((-)-Liangshanone)

  Mrv1652304282213372D          

 27 32  0  0  1  0            999 V2000
    1.5711    1.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8428    0.8241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167    0.5350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4023    0.5605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3177   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572   -0.8670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7032   -0.8169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8774    0.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201    0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2521   -0.4780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4537   -0.3475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2936   -0.7832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9167   -0.0794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4168   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9861   -1.0354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4313   -1.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7360   -2.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849   -1.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3482   -0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567   -0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7068    0.3471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8086    1.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7888   -1.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -1.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -1.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607    1.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  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  0  0  0  0
 10 11  1  0  0  0  0
 11  3  1  1  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  1  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
 10 23  1  1  0  0  0
 23 24  1  0  0  0  0
  7 25  1  6  0  0  0
  7 26  1  0  0  0  0
  2 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067218

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(C)CC[C@H](OC)[C@]34[C@@H]2C[C@H]([C@H]13)[C@@]12C[C@H](C(=C)[C@H]1O)C(=O)C[C@@H]42

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO3/c1-5-24-11-21(3)7-6-18(27-4)23-16(21)8-14(19(23)24)22-10-13(12(2)20(22)26)15(25)9-17(22)23/h13-14,16-20,26H,2,5-11H2,1,3-4H3/t13-,14-,16-,17-,18+,19+,20-,21-,22-,23-/m1/s1

> <INCHI_KEY>
NVVRRHYGTUDOIZ-PMJGNJIISA-N

> <FORMULA>
C23H33NO3

> <MOLECULAR_WEIGHT>
371.521

> <EXACT_MASS>
371.246043927

$$$$

Download
3D-SDF for NP0067218 ((-)-Liangshanone)
Download
PDB for NP0067218 ((-)-Liangshanone)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.933   2.992   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.440   1.538   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.884   0.999   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.351   1.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.193  -0.507   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.774  -1.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.179  -1.525   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.504   0.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.904   0.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.337  -0.892   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.580  -0.649   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.148  -1.462   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.311  -0.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.245  -1.086   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.307  -1.933   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.272  -3.185   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.840  -4.617   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.692  -2.989   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.983  -0.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.493  -0.144   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.786   0.648   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.976   2.176   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.472  -2.167   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.143  -3.553   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.330  -3.058   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.570   0.095   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.420   3.280   0.000  0.00  0.00           C+0
CONECT    1    2   27                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   25   26                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10    3    6   12                                             
CONECT   12   11   13   18                                                  
CONECT   13   12    4   14   21                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12                                                       
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21                                                            
CONECT   23   10   24                                                       
CONECT   24   23                                                            
CONECT   25    7                                                            
CONECT   26    7    2                                                       
CONECT   27    1                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

Download
3D PDB for NP0067218 ((-)-Liangshanone)
Download
SMILES for NP0067218 ((-)-Liangshanone)
CCN1C[C@@]2(C)CC[C@H](OC)[C@]34[C@@H]2C[C@H]([C@H]13)[C@@]12C[C@H](C(=C)[C@H]1O)C(=O)C[C@@H]42
Download
INCHI for NP0067218 ((-)-Liangshanone)
InChI=1S/C23H33NO3/c1-5-24-11-21(3)7-6-18(27-4)23-16(21)8-14(19(23)24)22-10-13(12(2)20(22)26)15(25)9-17(22)23/h13-14,16-20,26H,2,5-11H2,1,3-4H3/t13-,14-,16-,17-,18+,19+,20-,21-,22-,23-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC23H33NO3
Average Mass371.5210 Da
Monoisotopic Mass371.24604 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CCN1C[C@@]2(C)CC[C@H](OC)[C@]34[C@@H]2C[C@H]([C@H]13)[C@@]12C[C@H](C(=C)[C@H]1O)C(=O)C[C@@H]42
InChI Identifier
InChI=1S/C23H33NO3/c1-5-24-11-21(3)7-6-18(27-4)23-16(21)8-14(19(23)24)22-10-13(12(2)20(22)26)15(25)9-17(22)23/h13-14,16-20,26H,2,5-11H2,1,3-4H3/t13-,14-,16-,17-,18+,19+,20-,21-,22-,23-/m1/s1
InChI KeyNVVRRHYGTUDOIZ-PMJGNJIISA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aconitum liangshanicumLOTUS Database
Aconitum liangshaniumPlant
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentNapelline-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
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163105293  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available