NP-MRD: Showing NP-Card for 2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate (NP0246318)

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Record Information

Version

2.0

Created at

2022-09-07 07:44:50 UTC

Updated at

2022-09-07 07:44:50 UTC

NP-MRD ID

NP0246318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate

Description

2-[12-(Acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Icosan-7-yl]ethyl acetate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. 2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate is found in Spiraea japonica. 2-[12-(Acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Icosan-7-yl]ethyl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191520422D          

 32 37  0  0  0  0            999 V2000
    7.0715    4.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9471    2.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724    1.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004191520422D          

 32 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0246318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCCN1CC2(C)CCCC34C1OC(CC23)C12CCC(CC41)C(=C)C2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H37NO5/c1-15-18-6-9-26(22(15)31-17(3)29)20(12-18)25-8-5-7-24(4)14-27(10-11-30-16(2)28)23(25)32-21(26)13-19(24)25/h18-23H,1,5-14H2,2-4H3

> <INCHI_KEY>
OWDJZYOWYLOEJQ-UHFFFAOYSA-N

> <FORMULA>
C26H37NO5

> <MOLECULAR_WEIGHT>
443.584

> <EXACT_MASS>
443.267173295

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.54367772768428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.965833220333335

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
6.993408141146883

> <JCHEM_POLAR_SURFACE_AREA>
65.07

> <JCHEM_REFRACTIVITY>
117.65339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      13.200   8.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.621   7.166   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.114   6.790   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.548   6.062   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.968   4.580   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.895   3.475   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      12.315   1.994   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      13.822   1.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.739  -0.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.252   0.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.409  -1.525   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.383  -2.738   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.830  -2.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.893  -1.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.134  -0.261   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.426   0.028   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.014   0.719   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.072   1.882   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.250   0.779   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.030  -0.570   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.801   0.212   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.155  -1.482   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.958  -3.039   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.551  -3.054   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.320  -1.636   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.553  -2.295   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.090  -2.777   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.243  -0.858   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.321   0.376   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.792   0.195   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.184  -1.220   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.870   1.429   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19   25                                             
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    7   14                                                  
CONECT   20   17   21   25   28                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   14   20                                                  
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-[12-(Acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2,.0,.0,.0,]icosan-7-yl]ethyl acetic acid	Generator
2-[12-(Acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetic acid	Generator

Chemical Formula

C₂₆H₃₇NO₅

Average Mass

443.5840 Da

Monoisotopic Mass

443.26717 Da

IUPAC Name

2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate

Traditional Name

2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCCN1CC2(C)CCCC34C1OC(CC23)C12CCC(CC41)C(=C)C2OC(C)=O

InChI Identifier

InChI=1S/C26H37NO5/c1-15-18-6-9-26(22(15)31-17(3)29)20(12-18)25-8-5-7-24(4)14-27(10-11-30-16(2)28)23(25)32-21(26)13-19(24)25/h18-23H,1,5-14H2,2-4H3

InChI Key

OWDJZYOWYLOEJQ-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
Spiraea japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Dicarboxylic acid or derivatives
Oxane
Piperidine
Hemiaminal
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
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	3.02	ALOGPS
logP	2.97	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	6.99	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.65 m³·mol⁻¹	ChemAxon
Polarizability	48.54 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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 2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate (NP0246318)

MOL for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

3D MOL for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

3D SDF for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

3D-SDF for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

PDB for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

3D PDB for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

SMILES for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

INCHI for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

Structure for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)

3D Structure for NP0246318 (2-[12-(acetyloxy)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]icosan-7-yl]ethyl acetate)