NP-MRD: Showing NP-Card for 11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol (NP0281709)

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Record Information

Version

2.0

Created at

2022-09-09 08:13:49 UTC

Updated at

2022-09-09 08:13:49 UTC

NP-MRD ID

NP0281709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol

Description

11-Ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecane-8,13-diol 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. 11-Ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecane-8,13-diol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241515252D          

 33 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241515252D          

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 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
  5 30  1  0  0  0  0
 12 30  1  0  0  0  0
 24 31  1  0  0  0  0
  3 31  1  0  0  0  0
 12 31  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1CC2(O)CCC(OC)C34C5CC6C(OC)C5C(O)(CC6OC)C(OO)(C(OC)C23)C14

> <INCHI_IDENTIFIER>
InChI=1S/C24H39NO8/c1-6-25-11-21(26)8-7-15(30-3)23-13-9-12-14(29-2)10-22(27,16(13)17(12)31-4)24(33-28,20(23)25)19(32-5)18(21)23/h12-20,26-28H,6-11H2,1-5H3

> <INCHI_KEY>
OJTGVRVXRXFTNU-UHFFFAOYSA-N

> <FORMULA>
C24H39NO8

> <MOLECULAR_WEIGHT>
469.575

> <EXACT_MASS>
469.26756722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.44144157882198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
-1.1226937470000002

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.41766945328025

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.66858487635984

> <JCHEM_PKA_STRONGEST_BASIC>
9.098960714092215

> <JCHEM_POLAR_SURFACE_AREA>
110.08000000000003

> <JCHEM_REFRACTIVITY>
116.84469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.785  -5.272   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.631  -4.443   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.770  -2.925   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.723  -1.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.397  -0.152   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.024   0.661   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.830   1.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.331   1.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.313   0.627   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.876   2.276   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.681   3.938   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.923  -0.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.383  -0.182   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.740   0.873   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.271  -0.446   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.787  -2.024   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.633  -3.120   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.113  -2.739   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.506  -4.329   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.266  -1.186   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.469   0.198   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.755   1.407   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.198   2.181   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.419  -3.175   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.326  -4.880   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.600  -6.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.536  -2.541   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.832  -3.215   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.844  -3.085   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.704  -0.854   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.343  -2.804   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.401  -2.315   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.313  -3.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   30                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   30   31                                             
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   32                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   24                                             
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   18   25   27   31                                             
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27    5   12                                                  
CONECT   31   24    3   12                                                  
CONECT   32   16   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

11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol

Traditional Name

11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol

CAS Registry Number

Not Available

SMILES

CCN1CC2(O)CCC(OC)C34C5CC6C(OC)C5C(O)(CC6OC)C(OO)(C(OC)C23)C14

InChI Identifier

InChI=1S/C24H39NO8/c1-6-25-11-21(26)8-7-15(30-3)23-13-9-12-14(29-2)10-22(27,16(13)17(12)31-4)24(33-28,20(23)25)19(32-5)18(21)23/h12-20,26-28H,6-11H2,1-5H3

InChI Key

OJTGVRVXRXFTNU-UHFFFAOYSA-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
Quinolidine
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
1,2-aminoalcohol
Hydroperoxide
Organoheterocyclic compound
Azacycle
Alkyl hydroperoxide
Dialkyl ether
Peroxol
Ether
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Amine
Hydrocarbon derivative
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	0.4	ALOGPS
logP	-1.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	9.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.08 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.84 m³·mol⁻¹	ChemAxon
Polarizability	49.44 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol (NP0281709)

MOL for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

3D MOL for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

3D SDF for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

3D-SDF for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

PDB for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

3D PDB for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

SMILES for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

INCHI for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

Structure for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)

3D Structure for NP0281709 (11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-8,13-diol)