NP-MRD: Showing NP-Card for (1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol (NP0272347)

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Record Information

Version

2.0

Created at

2022-09-08 18:56:12 UTC

Updated at

2022-09-08 18:56:13 UTC

NP-MRD ID

NP0272347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol

Description

Delectinine belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. (1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol is found in Delphinium andersonii and Delphinium elatum. (1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol was first documented in 2003 (PMID: 12560023). Based on a literature review a small amount of articles have been published on Delectinine (PMID: 15387663) (PMID: 24452459) (PMID: 17575798) (PMID: 20550959).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082220562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082220562D          

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 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 13 29  1  0  0  0  0
 30 29  1  1  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0272347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(CO)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@](O)([C@@H](OC)[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C24H39NO7/c1-5-25-10-21(11-26)7-6-15(31-3)23-13-8-12-14(30-2)9-22(28,16(13)17(12)27)24(29,20(23)25)19(32-4)18(21)23/h12-20,26-29H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,17+,18-,19+,20+,21+,22-,23+,24-/m1/s1

> <INCHI_KEY>
NCFXPSTWPUGLEA-FCXNFKKQSA-N

> <FORMULA>
C24H39NO7

> <MOLECULAR_WEIGHT>
453.576

> <EXACT_MASS>
453.2726526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
48.75126612669368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5S,6S,8R,9S,10S,13S,16S,17R,18S)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8,9-triol

> <JCHEM_LOGP>
-2.0781366266666677

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.856423114304878

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210974855928686

> <JCHEM_PKA_STRONGEST_BASIC>
9.471530753004696

> <JCHEM_POLAR_SURFACE_AREA>
111.85000000000002

> <JCHEM_REFRACTIVITY>
115.5638

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5S,6S,8R,9S,10S,13S,16S,17R,18S)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8,9-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.711   3.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.016   1.553   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.182  -0.180   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.230  -1.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.555  -2.953   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.003  -3.842   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.784  -5.271   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.123  -4.494   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.379  -4.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.361  -3.733   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.002  -5.338   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.748  -6.946   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.970  -2.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.390  -0.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.467   0.070   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.483   1.692   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.584  -0.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.994   0.401   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.628   0.424   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.751  -2.251   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.160  -0.366   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.461   1.238   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.680   0.015   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.834  -1.081   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.438  -0.719   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.285   0.633   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.318  -2.659   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.787  -3.979   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.431  -2.924   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.314  -1.920   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.516  -3.304   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.066  -3.976   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   20                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   20   29                                             
CONECT   14   13    3   15                                                  
CONECT   15   14   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    5   13                                                  
CONECT   21   15   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   13   30                                                  
CONECT   30   29   21   31                                                  
CONECT   31   30   27   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₉NO₇

Average Mass

453.5760 Da

Monoisotopic Mass

453.27265 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(CO)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@](O)([C@@H](OC)[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C24H39NO7/c1-5-25-10-21(11-26)7-6-15(31-3)23-13-8-12-14(30-2)9-22(28,16(13)17(12)27)24(29,20(23)25)19(32-4)18(21)23/h12-20,26-29H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,17+,18-,19+,20+,21+,22-,23+,24-/m1/s1

InChI Key

NCFXPSTWPUGLEA-FCXNFKKQSA-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
Delphinium andersonii	LOTUS Database	35616633
Delphinium elatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Quinolidine
Alkaloid or derivatives
Azepane
Piperidine
1,3-aminoalcohol
Cyclic alcohol
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Polyol
Dialkyl ether
Ether
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary alcohol
Organic nitrogen compound
Amine
Hydrocarbon derivative
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

C00028157

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

101352912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shrestha PM, Katz A: Diterpenoid alkaloids from the roots of Delphinium scabriflorum. J Nat Prod. 2004 Sep;67(9):1574-6. doi: 10.1021/np0305066. [PubMed:15387663 ]
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 ]
Csupor D, Forgo P, Csedo K, Mathe I, Hohmann J: [Investigation of the diterpene alkaloids of Aconitum species native to the Carpathian Basin]. Acta Pharm Hung. 2006;76(4):181-90. [PubMed:17575798 ]
Batbayar N, Enkhzaya S, Tunsag J, Batsuren D, Rycroft DS, Sproll S, Bracher F: Norditerpenoid alkaloids from Delphinium species. Phytochemistry. 2003 Feb;62(4):543-50. doi: 10.1016/s0031-9422(02)00514-9. [PubMed:12560023 ]
He YQ, Ma ZY, Wei XM, Du BZ, Jing ZX, Yao BH, Gao LM: Chemical constituents from Delphinium chrysotrichum and their biological activity. Fitoterapia. 2010 Oct;81(7):929-31. doi: 10.1016/j.fitote.2010.06.008. Epub 2010 Jun 13. [PubMed:20550959 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol (NP0272347)

MOL for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

3D MOL for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

3D SDF for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

3D-SDF for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

PDB for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

3D PDB for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

SMILES for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

INCHI for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

Structure for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)

3D Structure for NP0272347 ((1s,2r,3r,4s,5s,6s,8r,9s,10s,13s,16s,17r,18s)-11-ethyl-13-(hydroxymethyl)-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8,9-triol)