NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol (NP0292831)

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Record Information

Version

2.0

Created at

2022-09-10 00:33:24 UTC

Updated at

2022-09-10 00:33:24 UTC

NP-MRD ID

NP0292831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol

Description

Crassicaulidine 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. (2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol is found in Aconitum hemsleyanum. Based on a literature review very few articles have been published on Crassicaulidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202332D          

 33 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102202332D          

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 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 24  1  6  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(COC)[C@H]3[C@@H](OC)C4C1C3([C@@H]1C[C@H]3[C@H](O)[C@@H]1[C@]4(O)[C@H](O)[C@@H]3OC)[C@@H](O)C[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C24H39NO8/c1-5-25-8-22(9-31-2)12(26)7-13(27)23-11-6-10-16(28)14(11)24(30,21(29)17(10)32-3)15(20(23)25)18(33-4)19(22)23/h10-21,26-30H,5-9H2,1-4H3/t10-,11+,12+,13-,14+,15?,16-,17+,18-,19+,20?,21+,22-,23?,24+/m0/s1

> <INCHI_KEY>
BHISMAZIHGUBPO-WUFPVXNBSA-N

> <FORMULA>
C24H39NO8

> <MOLECULAR_WEIGHT>
469.575

> <EXACT_MASS>
469.26756722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.19798717497404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R,7R,8R,13R,14R,16S,17S,18R)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,7,8,14,16-pentol

> <JCHEM_LOGP>
-3.311684307666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.831499981125031

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.76477860973457

> <JCHEM_PKA_STRONGEST_BASIC>
9.169114364532794

> <JCHEM_POLAR_SURFACE_AREA>
132.08

> <JCHEM_REFRACTIVITY>
116.8381

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R,7R,8R,13R,14R,16S,17S,18R)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,7,8,14,16-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.228  -6.120   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.697  -4.598   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.171  -2.930   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.510  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.359   0.650   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.060   2.292   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.706   3.725   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.238   3.879   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.721   0.635   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.538  -1.173   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.310  -2.036   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.037  -1.993   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.225  -1.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.020  -1.916   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.176  -0.066   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.464  -0.914   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.971  -2.761   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.119   0.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.467  -0.851   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.922  -2.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.659   0.968   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.967   2.178   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.730   1.187   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.798   1.598   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.358   3.154   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.767   0.123   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.890  -1.400   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.276  -2.942   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.500  -1.549   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.294  -2.972   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.493  -0.287   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.144  -0.342   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.158   0.856   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   19                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   15                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   27                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14    9   16   21                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    5   20                                                  
CONECT   20   19                                                            
CONECT   21   15   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   21   27                                                  
CONECT   27   26   13   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₉NO₈

Average Mass

469.5750 Da

Monoisotopic Mass

469.26757 Da

IUPAC Name

(2R,3R,4S,5S,6R,7R,8R,13R,14R,16S,17S,18R)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,7,8,14,16-pentol

Traditional Name

(2R,3R,4S,5S,6R,7R,8R,13R,14R,16S,17S,18R)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,7,8,14,16-pentol

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(COC)[C@H]3[C@@H](OC)C4C1C3([C@@H]1C[C@H]3[C@H](O)[C@@H]1[C@]4(O)[C@H](O)[C@@H]3OC)[C@@H](O)C[C@H]2O

InChI Identifier

InChI=1S/C24H39NO8/c1-5-25-8-22(9-31-2)12(26)7-13(27)23-11-6-10-16(28)14(11)24(30,21(29)17(10)32-3)15(20(23)25)18(33-4)19(22)23/h10-21,26-30H,5-9H2,1-4H3/t10-,11+,12+,13-,14+,15?,16-,17+,18-,19+,20?,21+,22-,23?,24+/m0/s1

InChI Key

BHISMAZIHGUBPO-WUFPVXNBSA-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 hemsleyanum	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
Azacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	-3.3	ChemAxon
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	9.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.08 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.84 m³·mol⁻¹	ChemAxon
Polarizability	50.2 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

Not Available

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

158562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol (NP0292831)

MOL for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

3D MOL for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

3D SDF for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

3D-SDF for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

PDB for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

3D PDB for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

SMILES for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

INCHI for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

Structure for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)

3D Structure for NP0292831 ((2r,3r,4s,5s,6r,7r,8r,13r,14r,16s,17s,18r)-11-ethyl-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,7,8,14,16-pentol)