NP-MRD: Showing NP-Card for (1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one (NP0256037)

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Record Information

Version

1.0

Created at

2022-09-07 20:44:40 UTC

Updated at

2022-09-07 20:44:40 UTC

NP-MRD ID

NP0256037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one

Description

14-Dehydrodelcosine 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,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one is found in Aconitum japonicum, Aconitum sachalinense, Delphinium nuttallianum and Delphinium occidentale. It was first documented in 2002 (PMID: 35412727). Based on a literature review a significant number of articles have been published on 14-Dehydrodelcosine (PMID: 36099392) (PMID: 31661213) (PMID: 31593386) (PMID: 12560023).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222442D          

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M  END

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  Mrv1652309072222442D          

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M  END
> <DATABASE_ID>
NP0256037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6[C@H](C[C@@](O)([C@H]5C6=O)C(O)([C@@H](OC)[C@H]23)[C@@H]14)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H37NO7/c1-5-25-10-21(11-30-2)7-6-15(26)23-13-8-12-14(31-3)9-22(28,16(13)17(12)27)24(29,20(23)25)19(32-4)18(21)23/h12-16,18-20,26,28-29H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,18-,19+,20+,21+,22-,23+,24?/m1/s1

> <INCHI_KEY>
ZXVJFGOQJRGEPX-FHKWXJSFSA-N

> <FORMULA>
C24H37NO7

> <MOLECULAR_WEIGHT>
451.56

> <EXACT_MASS>
451.257002535

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.242006510194734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3S,5R,6S,8R,10S,13S,16S,17R,18S)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-one

> <JCHEM_LOGP>
-1.2859074550000011

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.372050654841313

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.029882555677649

> <JCHEM_PKA_STRONGEST_BASIC>
8.78209300880891

> <JCHEM_POLAR_SURFACE_AREA>
108.69000000000003

> <JCHEM_REFRACTIVITY>
114.63109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,5R,6S,8R,10S,13S,16S,17R,18S)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.137   3.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.046   1.486   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      -1.975  -3.869   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.355  -5.424   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.833  -5.855   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.123  -4.494   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.379  -4.926   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.361  -3.733   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.503  -4.782   0.000  0.00  0.00           O+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       2.632   1.672   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      -1.107   0.214   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.775   0.331   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       4.501   1.253   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       8.401  -0.667   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.162   0.732   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       6.686  -4.481   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    9   20                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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

C₂₄H₃₇NO₇

Average Mass

451.5600 Da

Monoisotopic Mass

451.25700 Da

IUPAC Name

(1S,2R,3S,5R,6S,8R,10S,13S,16S,17R,18S)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-one

Traditional Name

(1S,2R,3S,5R,6S,8R,10S,13S,16S,17R,18S)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-one

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6[C@H](C[C@@](O)([C@H]5C6=O)C(O)([C@@H](OC)[C@H]23)[C@@H]14)OC

InChI Identifier

InChI=1S/C24H37NO7/c1-5-25-10-21(11-30-2)7-6-15(26)23-13-8-12-14(31-3)9-22(28,16(13)17(12)27)24(29,20(23)25)19(32-4)18(21)23/h12-16,18-20,26,28-29H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,18-,19+,20+,21+,22-,23+,24?/m1/s1

InChI Key

ZXVJFGOQJRGEPX-FHKWXJSFSA-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 japonicum	LOTUS Database	35616633
Aconitum sachalinense	LOTUS Database	35616633
Delphinium nuttallianum	LOTUS Database	35616633
Delphinium occidentale	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
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Polyol
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 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
logP	-1.3	ChemAxon
pKa (Strongest Acidic)	12.03	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.63 m³·mol⁻¹	ChemAxon
Polarizability	48.24 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00027685

Chemspider ID

108341269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134715256

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Freebody J: "The Root of All Evil is Inactivity": The Response of French Psychiatrists to New Approaches to Patient Work and Occupation, 1918-1939. 2021. [PubMed:36099392 ]
Authors unspecified: Childhood Pulmonary Inflammatory Myofibroblastic Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:35412727 ]
Authors unspecified: Childhood Adrenocortical Carcinoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31661213 ]
Authors unspecified: Childhood Breast Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593386 ]
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 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one (NP0256037)

MOL for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D MOL for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D SDF for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D-SDF for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

PDB for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D PDB for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

SMILES for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

INCHI for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

Structure for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D Structure for NP0256037 ((1s,2r,3s,5r,6s,8r,10s,13s,16s,17r,18s)-11-ethyl-8,9,16-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)