NP-MRD: Showing NP-Card for 1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one (NP0245396)

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Record Information

Version

2.0

Created at

2022-09-07 06:28:00 UTC

Updated at

2022-09-07 06:28:01 UTC

NP-MRD ID

NP0245396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one

Description

1-[(1S,4S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]Octan-4-yl]-3-[(3R,7S,10R,13R)-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]Hexadecan-2-yl]propan-1-one belongs to the class of organic compounds known as daphniphylline-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum, possessing 22 carbon polycyclic fused ring systems with or without the C8 side chain. The C8 unit consists of 6-oxabicyclo[3.2.1]Octane or 2,8-dioxabicyclo[3.2.1]Octane. 1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one is found in Daphniphyllum calycinum and Daphniphyllum oldhamii. Based on a literature review very few articles have been published on 1-[(1S,4S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]Octan-4-yl]-3-[(3R,7S,10R,13R)-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]Hexadecan-2-yl]propan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208282D          

 34 40  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309072208282D          

 34 40  0  0  1  0            999 V2000
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    0.0115    2.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359    1.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0605    1.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956    1.9584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3935    1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383    2.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7070    3.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9524    2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8813    2.5930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -1.2983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5644   -1.5996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1760   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  6  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 17 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  1  0  0  0
 12 33  1  6  0  0  0
 33 34  1  0  0  0  0
  9 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245396

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC2(C)[C@H]3CC[C@@]45CCC[C@@H]4C2(CCC(=O)[C@@]2(C)CO[C@]4(C)CCC2O4)[C@@H]1N5C3

> <INCHI_IDENTIFIER>
InChI=1S/C30H47NO3/c1-19(2)21-9-13-27(4)20-8-15-29-12-6-7-22(29)30(27,25(21)31(29)17-20)16-10-23(32)26(3)18-33-28(5)14-11-24(26)34-28/h19-22,24-25H,6-18H2,1-5H3/t20-,21?,22-,24?,25+,26+,27?,28-,29-,30?/m0/s1

> <INCHI_KEY>
REKWVHVBDQXQLB-ZNPODFJCSA-N

> <FORMULA>
C30H47NO3

> <MOLECULAR_WEIGHT>
469.71

> <EXACT_MASS>
469.355594377

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.63352070831577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(1S,4S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3R,7S,10R,13R)-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-2-yl]propan-1-one

> <JCHEM_LOGP>
5.631143509333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.839853721399113

> <JCHEM_PKA_STRONGEST_BASIC>
11.959476992920797

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
134.18119999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,4S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3R,7S,10R,13R)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-2-yl]propan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.920  -3.483   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.384  -3.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.712  -4.979   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.520  -2.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.190  -0.920   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.321   0.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.738   0.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.003   1.501   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.363  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.015  -3.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.642  -3.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.100  -2.011   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.544  -2.018   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.164  -0.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.047   0.373   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.384  -0.498   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.934  -0.585   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.418   0.866   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.903   1.145   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.388   2.596   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.127   2.875   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.387   3.768   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.022   4.481   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.307   2.534   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.846   2.484   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.845   3.656   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.334   3.264   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.551   5.168   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.186   5.880   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.778   5.258   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.512   4.840   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.955  -2.423   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       2.920  -2.986   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       4.062  -1.653   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16   33                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16    7   18   32                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   30                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   31                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   22   31                                                  
CONECT   31   30   26                                                       
CONECT   32   17    4   33                                                  
CONECT   33   32   12   34                                                  
CONECT   34   33    9                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₇NO₃

Average Mass

469.7100 Da

Monoisotopic Mass

469.35559 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC2(C)[C@H]3CC[C@@]45CCC[C@@H]4C2(CCC(=O)[C@@]2(C)CO[C@]4(C)CCC2O4)[C@@H]1N5C3

InChI Identifier

InChI=1S/C30H47NO3/c1-19(2)21-9-13-27(4)20-8-15-29-12-6-7-22(29)30(27,25(21)31(29)17-20)16-10-23(32)26(3)18-33-28(5)14-11-24(26)34-28/h19-22,24-25H,6-18H2,1-5H3/t20-,21?,22-,24?,25+,26+,27?,28-,29-,30?/m0/s1

InChI Key

REKWVHVBDQXQLB-ZNPODFJCSA-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
Daphniphyllum calycinum	LOTUS Database	35616633
Daphniphyllum oldhamii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as daphniphylline-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum, possessing 22 carbon polycyclic fused ring systems with or without the C8 side chain. The C8 unit consists of 6-oxabicyclo[3.2.1]Octane or 2,8-dioxabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Daphniphylline-type alkaloids

Sub Class

Not Available

Direct Parent

Daphniphylline-type alkaloids

Alternative Parents

Substituents

Daphniphylline-type alkaloid
Sesquiterpenoid
Azaspirodecane
Indolizidine
Indole or derivatives
Ketal
Oxepane
Azepane
N-alkylpyrrolidine
Piperidine
Meta-dioxane
Tetrahydrofuran
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Ketone
Oxacycle
Azacycle
Organoheterocyclic compound
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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

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

138113965

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one (NP0245396)

MOL for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

3D MOL for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

3D SDF for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

3D-SDF for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

PDB for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

3D PDB for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

SMILES for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

INCHI for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

Structure for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)

3D Structure for NP0245396 (1-[(1s,4s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3r,7s,10r,13r)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-2-yl]propan-1-one)