NP-MRD: Showing NP-Card for 14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate (NP0184439)

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Record Information

Version

2.0

Created at

2022-09-03 23:34:09 UTC

Updated at

2022-09-03 23:34:09 UTC

NP-MRD ID

NP0184439

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate

Description

14-Ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docosan-4-yl acetate belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene. 14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate is found in Delphinium barbeyi. 14-Ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docosan-4-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171503062D          

 35 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171503062D          

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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 12 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184439

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1CC2(C)CCC(OC)C34C1C1(OCOC11CC(OC)C5CC3(O)C1C5OC(C)=O)C(=O)C24

> <INCHI_IDENTIFIER>
InChI=1S/C26H37NO8/c1-6-27-11-22(3)8-7-16(32-5)25-19(22)20(29)26(21(25)27)24(33-12-34-26)10-15(31-4)14-9-23(25,30)18(24)17(14)35-13(2)28/h14-19,21,30H,6-12H2,1-5H3

> <INCHI_KEY>
JGUCDDHPUGUZEN-UHFFFAOYSA-N

> <FORMULA>
C26H37NO8

> <MOLECULAR_WEIGHT>
491.581

> <EXACT_MASS>
491.251917155

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.17756655341316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
0.06878298666666732

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.80129091183969

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.433035847310418

> <JCHEM_PKA_STRONGEST_BASIC>
8.441511045996402

> <JCHEM_POLAR_SURFACE_AREA>
103.75999999999999

> <JCHEM_REFRACTIVITY>
120.98019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -2.510   2.214   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.965   1.600   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      -2.182  -3.542   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.240  -4.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.272  -4.789   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.237  -3.578   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.227  -5.315   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.930  -6.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.844  -1.976   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.263  -0.165   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.345   0.273   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.379   1.891   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.788   2.520   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.749   1.338   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.098  -0.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.702   0.074   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.859  -1.006   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.481  -0.736   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.403   0.568   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.301  -2.547   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.725  -3.800   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.358  -2.730   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.612  -4.472   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.255  -1.722   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.450  -3.119   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.824  -4.066   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.025  -5.103   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.480  -4.597   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.736  -6.615   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.456  -0.479   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.382  -0.006   0.000  0.00  0.00           O+0
HETATM   35  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   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   35                                             
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   25   35                                             
CONECT   13   12    3   14                                                  
CONECT   14   13   15   18   33                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19   27                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   12   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   14   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    5   12                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Value	Source
14-Ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1,.0,.0,.0,.0,]docosan-4-yl acetic acid	Generator
14-Ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₇NO₈

Average Mass

491.5810 Da

Monoisotopic Mass

491.25192 Da

IUPAC Name

14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate

Traditional Name

14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CCN1CC2(C)CCC(OC)C34C1C1(OCOC11CC(OC)C5CC3(O)C1C5OC(C)=O)C(=O)C24

InChI Identifier

InChI=1S/C26H37NO8/c1-6-27-11-22(3)8-7-16(32-5)25-19(22)20(29)26(21(25)27)24(33-12-34-26)10-15(31-4)14-9-23(25,30)18(24)17(14)35-13(2)28/h14-19,21,30H,6-12H2,1-5H3

InChI Key

JGUCDDHPUGUZEN-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

Species Name	Source	Reference
Delphinium barbeyi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthroindolizidines

Direct Parent

Phenanthroindolizidines

Alternative Parents

Substituents

Phenanthroindolizidine
Naphthalene
Tetrahydroisoquinoline
Indolizidine
Anisole
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Pyrrolidine
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ether
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.14	ALOGPS
logP	0.069	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	8.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.98 m³·mol⁻¹	ChemAxon
Polarizability	51.18 Å³	ChemAxon
Number of Rings	7	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

14314600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate (NP0184439)

MOL for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

3D MOL for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

3D SDF for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

3D-SDF for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

PDB for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

3D PDB for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

SMILES for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

INCHI for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

Structure for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)

3D Structure for NP0184439 (14-ethyl-2-hydroxy-6,19-dimethoxy-16-methyl-21-oxo-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-4-yl acetate)