NP-MRD: Showing NP-Card for (1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate (NP0159435)

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Record Information

Version

2.0

Created at

2022-09-02 17:11:12 UTC

Updated at

2022-09-02 17:11:12 UTC

NP-MRD ID

NP0159435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate

Description

(1R,2R,3R,4R,5R,6R,8S,12S,13S,16R,19S,20R,21R)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docosan-21-yl acetate 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. Based on a literature review very few articles have been published on (1R,2R,3R,4R,5R,6R,8S,12S,13S,16R,19S,20R,21R)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docosan-21-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219112D          

 34 40  0  0  1  0            999 V2000
   -1.5459    1.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438    0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9784   -2.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9877   -1.0585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 31 33  2  0  0  0  0
 34 29  1  1  0  0  0
  5 34  1  0  0  0  0
 11 34  1  0  0  0  0
M  END

     RDKit          3D

 71 77  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309022219112D          

 34 40  0  0  1  0            999 V2000
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 11 12  1  1  0  0  0
 12  3  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 24  1  6  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 13 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 34 29  1  1  0  0  0
  5 34  1  0  0  0  0
 11 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@H]2CC[C@H](OC)[C@]34[C@@H]2[C@@H](OC(C)=O)[C@@]2(OCO[C@]22C[C@@H](OC)[C@@H]5C[C@@]3(O)[C@H]2[C@@H]5O)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO8/c1-5-26-10-13-6-7-16(31-4)24-17(13)20(34-12(2)27)25(21(24)26)23(32-11-33-25)9-15(30-3)14-8-22(24,29)19(23)18(14)28/h13-21,28-29H,5-11H2,1-4H3/t13-,14-,15+,16-,17-,18+,19+,20+,21-,22+,23-,24+,25+/m0/s1

> <INCHI_KEY>
OTRLHYKIRJOZHW-JOHFOTPWSA-N

> <FORMULA>
C25H37NO8

> <MOLECULAR_WEIGHT>
479.57

> <EXACT_MASS>
479.251917155

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.76174797057385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,4R,5R,6R,8S,12S,13S,16R,19S,20R,21R)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosan-21-yl acetate

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
-1.0507590209999975

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.626387841469793

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.740369601129256

> <JCHEM_PKA_STRONGEST_BASIC>
9.512664126581786

> <JCHEM_POLAR_SURFACE_AREA>
106.92000000000002

> <JCHEM_REFRACTIVITY>
117.30149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,4R,5R,6R,8S,12S,13S,16R,19S,20R,21R)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosan-21-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.886   2.110   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.388   1.475   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.292  -0.011   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.361  -1.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.714  -2.813   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.240  -4.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.272  -4.789   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.237  -3.578   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.693  -4.765   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.045  -6.415   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.844  -1.976   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.263  -0.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.345   0.273   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.379   1.891   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.788   2.520   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.749   1.338   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.098  -0.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.702   0.074   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.859  -1.006   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.481  -0.790   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.704  -1.783   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.301  -2.547   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.725  -3.800   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.358  -2.730   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.736  -4.462   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.255  -1.722   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.450  -3.119   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.835  -4.192   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.456  -0.479   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.226   0.250   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.851   0.129   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.520  -1.259   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.718   1.401   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.594  -2.146   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   24   34                                             
CONECT   12   11    3   13                                                  
CONECT   13   12   14   17   29                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18   26                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   11   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   13   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3R,4R,5R,6R,8S,12S,13S,16R,19S,20R,21R)-14-Ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1,.0,.0,.0,.0,]docosan-21-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₇NO₈

Average Mass

479.5700 Da

Monoisotopic Mass

479.25192 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1C[C@@H]2CC[C@H](OC)[C@]34[C@@H]2[C@@H](OC(C)=O)[C@@]2(OCO[C@]22C[C@@H](OC)[C@@H]5C[C@@]3(O)[C@H]2[C@@H]5O)[C@@H]14

InChI Identifier

InChI=1S/C25H37NO8/c1-5-26-10-13-6-7-16(31-4)24-17(13)20(34-12(2)27)25(21(24)26)23(32-11-33-25)9-15(30-3)14-8-22(24,29)19(23)18(14)28/h13-21,28-29H,5-11H2,1-4H3/t13-,14-,15+,16-,17-,18+,19+,20+,21-,22+,23-,24+,25+/m0/s1

InChI Key

OTRLHYKIRJOZHW-JOHFOTPWSA-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
Tertiary alcohol
Cyclic alcohol
Meta-dioxolane
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
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

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

163105438

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate (NP0159435)

MOL for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

3D MOL for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

3D SDF for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

3D-SDF for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

PDB for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

3D PDB for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

SMILES for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

INCHI for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

Structure for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)

3D Structure for NP0159435 ((1r,2r,3r,4r,5r,6r,8s,12s,13s,16r,19s,20r,21r)-14-ethyl-2,4-dihydroxy-6,19-dimethoxy-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-yl acetate)