NP-MRD: Showing NP-Card for Lannaconitine (NP0138902)

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Record Information

Version

2.0

Created at

2022-06-29 19:22:25 UTC

Updated at

2022-06-29 19:22:25 UTC

NP-MRD ID

NP0138902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lannaconitine

Description

Lappaconitine belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position. Lannaconitine was first documented in 2022 (PMID: 35469829). Based on a literature review a small amount of articles have been published on lappaconitine (PMID: 35620295) (PMID: 35739330) (PMID: 35643327) (PMID: 35556222).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221222D          

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M  END

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M  END


  Mrv1652306292221222D          

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    2.3162   -1.0433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9615   -1.7836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8892   -2.6054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733   -0.7155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651   -0.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    0.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0767   -2.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -2.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0643   -1.8895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -2.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -2.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5656   -3.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -2.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8435   -3.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7063   -4.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0668   -4.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7028   -4.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4759   -4.3301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131   -5.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -5.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3862   -5.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
  3 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  1  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 20 24  1  6  0  0  0
 16 25  1  6  0  0  0
 25 26  1  0  0  0  0
 14 27  1  6  0  0  0
  8 28  1  1  0  0  0
 28 29  1  0  0  0  0
  5 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@H](C[C@H]23)C14)OC(=O)C1=CC=CC=C1NC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H44N2O8/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35)/t19-,20-,22+,23-,24+,25+,26?,27+,29-,30+,31+,32+/m1/s1

> <INCHI_KEY>
NWBWCXBPKTTZNQ-MUVXNFNYSA-N

> <FORMULA>
C32H44N2O8

> <MOLECULAR_WEIGHT>
584.71

> <EXACT_MASS>
584.309766385

> <ALOGPS_LOGP>
1.95

> <ALOGPS_LOGS>
-3.33

> <ALOGPS_SOLUBILITY>
2.74e-01 g/l

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.615   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.078   1.214   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.386  -0.162   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.220  -1.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.543  -2.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.108  -4.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.394  -4.958   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.375  -3.764   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.981  -2.157   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.762  -2.285   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.591  -0.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.473   0.039   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.398  -0.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.167  -0.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.687  -0.011   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.842  -1.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.329  -2.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.801  -4.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.442  -2.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.324  -1.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.528  -3.329   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.393  -4.863   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.654  -5.747   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.737  -1.336   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.335  -0.724   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.752   0.758   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.170   1.146   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.877  -4.105   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.332  -5.576   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.987  -3.527   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.243  -5.046   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.686  -5.583   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.056  -6.027   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.387  -5.489   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.575  -6.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.318  -7.989   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.125  -8.526   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.312  -7.545   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      -2.755  -8.083   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0      -3.011  -9.601   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.824 -10.582   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.454 -10.139   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   30                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10   13   19                                             
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    9    3                                                  
CONECT   14   12   15   20   27                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   14   21   24                                             
CONECT   21   20   17   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20                                                            
CONECT   25   16   26                                                       
CONECT   26   25                                                            
CONECT   27   14                                                            
CONECT   28    8   29                                                       
CONECT   29   28                                                            
CONECT   30    5   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
Lappacontine	MeSH

Chemical Formula

C₃₂H₄₄N₂O₈

Average Mass

584.7100 Da

Monoisotopic Mass

584.30977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

32854-75-4

SMILES

CCN1C[C@@]2(CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@H](C[C@H]23)C14)OC(=O)C1=CC=CC=C1NC(C)=O

InChI Identifier

InChI=1S/C32H44N2O8/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35)/t19-,20-,22+,23-,24+,25+,26?,27+,29-,30+,31+,32+/m1/s1

InChI Key

NWBWCXBPKTTZNQ-MUVXNFNYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Lappaconitine-type diterpenoid alkaloids

Alternative Parents

Substituents

Lappaconitine-type diterpenoid alkaloid
Acylaminobenzoic acid or derivatives
Acetanilide
Benzoate ester
Quinolidine
Benzoic acid or derivatives
N-acetylarylamine
Alkaloid or derivatives
Anilide
Benzoyl
N-arylamide
Azepane
Monocyclic benzene moiety
Piperidine
Benzenoid
Vinylogous amide
Acetamide
Cyclic alcohol
Tertiary alcohol
Amino acid or derivatives
1,2-diol
Carboxamide group
Carboxylic acid ester
Tertiary aliphatic amine
Secondary carboxylic acid amide
Tertiary amine
Dialkyl ether
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

C00001650

Chemspider ID

21468867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281279

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang L, Miao X, Li Y, Hu F, Ma D, Zhang Z, Sun Q, Zhu Y, Zhu Q: Traditional processing, uses, phytochemistry, pharmacology and toxicology of Aconitum sinomontanum Nakai: A comprehensive review. J Ethnopharmacol. 2022 Jul 15;293:115317. doi: 10.1016/j.jep.2022.115317. Epub 2022 Apr 22. [PubMed:35469829 ]
Jiang W, Tang M, Yang L, Zhao X, Gao J, Jiao Y, Li T, Tie C, Gao T, Han Y, Jiang JD: Analgesic Alkaloids Derived From Traditional Chinese Medicine in Pain Management. Front Pharmacol. 2022 May 10;13:851508. doi: 10.3389/fphar.2022.851508. eCollection 2022. [PubMed:35620295 ]
Tsorin IB, Teplov IY, Zinchenko VP, Vititnova MB, Tsyrlina EM, Yunusov MS, Kryzhanovskii SA: Analysis of Electrophysiological Mechanisms of N-Deacetyllapaconitine Monochlorhydrate, the Main Metabolite of Lappaconitine Hydrobromide. Bull Exp Biol Med. 2022 Jun;173(2):219-223. doi: 10.1007/s10517-022-05522-2. Epub 2022 Jun 24. [PubMed:35739330 ]
Chiu KM, Lin TY, Lee MY, Lu CW, Wang SJ: Lappaconitine inhibits glutamate release from rat cerebrocortical nerve terminals by suppressing Ca(2+) influx and protein kinase A cascade. Neurotoxicology. 2022 Jul;91:218-227. doi: 10.1016/j.neuro.2022.05.014. Epub 2022 May 25. [PubMed:35643327 ]
McCabe DJ: Clinical Effects from Ingestion of Lappaconitine, an Aconitum Alkaloid with Sodium Channel Blocking Effects. J Med Toxicol. 2022 Jul;18(3):243-247. doi: 10.1007/s13181-022-00896-1. Epub 2022 May 13. [PubMed:35556222 ]

Showing NP-Card for Lannaconitine (NP0138902)

MOL for NP0138902 (Lannaconitine)

3D MOL for NP0138902 (Lannaconitine)

3D SDF for NP0138902 (Lannaconitine)

3D-SDF for NP0138902 (Lannaconitine)

PDB for NP0138902 (Lannaconitine)

3D PDB for NP0138902 (Lannaconitine)

SMILES for NP0138902 (Lannaconitine)

INCHI for NP0138902 (Lannaconitine)

Structure for NP0138902 (Lannaconitine)

3D Structure for NP0138902 (Lannaconitine)