NP-MRD: Showing NP-Card for (1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate (NP0285979)

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Record Information

Version

2.0

Created at

2022-09-09 14:22:25 UTC

Updated at

2022-09-09 14:22:25 UTC

NP-MRD ID

NP0285979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate

Description

(1R,2S,3S,4S,5S,6R,8R,9R,10S,13R,16R,17S)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl acetate 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. Based on a literature review very few articles have been published on (1R,2S,3S,4S,5S,6R,8R,9R,10S,13R,16R,17S)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216222D          

 32 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092216222D          

 32 37  0  0  1  0            999 V2000
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 13 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32  3  1  6  0  0  0
 13 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285979

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO6/c1-5-26-11-23(12-30-3)7-6-19(28)25-15-8-14-17(31-4)10-24(29,16(22(25)26)9-18(23)25)20(15)21(14)32-13(2)27/h14-22,28-29H,5-12H2,1-4H3/t14-,15-,16+,17+,18-,19+,20-,21-,22-,23+,24+,25-/m0/s1

> <INCHI_KEY>
ZEBMMHUDQRRILP-YMRBYOHMSA-N

> <FORMULA>
C25H39NO6

> <MOLECULAR_WEIGHT>
449.588

> <EXACT_MASS>
449.27773798

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.8872236326842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.4721000010000011

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.752661453550434

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.00798355132332

> <JCHEM_PKA_STRONGEST_BASIC>
9.842202932618891

> <JCHEM_POLAR_SURFACE_AREA>
88.46000000000001

> <JCHEM_REFRACTIVITY>
117.43769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.611  -4.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.926  -4.371   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.618  -2.995   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.783  -1.614   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.460  -0.167   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.017   0.370   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.239   1.889   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.948   2.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.896   1.372   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.398   1.802   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.378   0.607   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.880   0.948   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.985  -0.999   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.447  -0.204   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.805   0.849   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.334  -0.473   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.533   0.173   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.398   1.707   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.659   2.591   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.524   4.125   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.055   1.941   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.328  -1.209   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.171  -2.762   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.174  -4.302   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.691  -3.146   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.847  -2.052   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.339  -2.433   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.755  -3.915   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.477  -3.195   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.595  -2.558   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.766  -0.872   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.401  -2.823   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   31                                             
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   31   32                                             
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   14   23                                                  
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   16   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   23   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30    5   13                                                  
CONECT   32   29    3   13                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4S,5S,6R,8R,9R,10S,13R,16R,17S)-11-Ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-4-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₉NO₆

Average Mass

449.5880 Da

Monoisotopic Mass

449.27774 Da

IUPAC Name

(1R,2S,3S,4S,5S,6R,8R,9R,10S,13R,16R,17S)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl acetate

Traditional Name

(1R,2S,3S,4S,5S,6R,8R,9R,10S,13R,16R,17S)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H39NO6/c1-5-26-11-23(12-30-3)7-6-19(28)25-15-8-14-17(31-4)10-24(29,16(22(25)26)9-18(23)25)20(15)21(14)32-13(2)27/h14-22,28-29H,5-12H2,1-4H3/t14-,15-,16+,17+,18-,19+,20-,21-,22-,23+,24+,25-/m0/s1

InChI Key

ZEBMMHUDQRRILP-YMRBYOHMSA-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 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
Cyclic alcohol
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Amine
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	-0.47	ChemAxon
pKa (Strongest Acidic)	14.01	ChemAxon
pKa (Strongest Basic)	9.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.44 m³·mol⁻¹	ChemAxon
Polarizability	49.89 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	Yes	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

162866079

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate (NP0285979)

MOL for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D MOL for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D SDF for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D-SDF for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

PDB for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D PDB for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

SMILES for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

INCHI for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

Structure for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D Structure for NP0285979 ((1r,2s,3s,4s,5s,6r,8r,9r,10s,13r,16r,17s)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)