NP-MRD: Showing NP-Card for Isogilletine N-oxide (NP0068051)

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Record Information

Version

2.0

Created at

2022-04-28 12:56:55 UTC

Updated at

2022-04-28 12:56:55 UTC

NP-MRD ID

NP0068051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isogilletine N-oxide

Description

Isogilletine N-oxide is found in Triclisia gilletii (De Wild.) Staner . Based on a literature review very few articles have been published on (1R,14S)-25-hydroxy-9,20-dimethoxy-15-methyl-7,23,33-trioxa-15λ⁵,30-diazaoctacyclo[19.9.3.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁴,³².0²⁷,³¹.0²²,³⁴]Heptatriaconta-3,5,8,10,12(35),18,20,22(34),24,26,31,36-dodecaen-15-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214562D          

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M  END

     RDKit          3D

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M  CHG  2  40   1  42  -1
M  END


  Mrv1652304282214562D          

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    6.8261   -5.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2632   -6.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7319   -7.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298   -5.3694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581   -5.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666   -4.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132   -3.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266   -3.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360   -2.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140   -1.3912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2528   -1.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -2.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4991   -3.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3025   -3.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880   -3.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727   -2.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678   -2.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8049   -1.3078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1019   -4.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -4.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7285   -3.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17  7  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  1 37  1  0  0  0  0
 37 38  1  0  0  0  0
 35 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 33 41  1  1  0  0  0
 31 42  1  0  0  0  0
 42 43  2  0  0  0  0
 28 43  1  0  0  0  0
 15 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4=CC(OC5=CC=C(C[C@H]6NCCC7=C6C6=C(OC3=C1O6)C(O)=C7)C=C5)=C(OC)C=C4)N(C)(=O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C35H34N2O7/c1-37(39)13-11-22-18-29(41-3)33-35-31(22)25(37)15-20-6-9-27(40-2)28(16-20)42-23-7-4-19(5-8-23)14-24-30-21(10-12-36-24)17-26(38)32(43-35)34(30)44-33/h4-9,16-18,24-25,36,38H,10-15H2,1-3H3/t24-,25+,37?/m1/s1

> <INCHI_KEY>
DJJSAIRLTRARJX-IRDRIFKTSA-N

> <FORMULA>
C35H34N2O7

> <MOLECULAR_WEIGHT>
594.664

> <EXACT_MASS>
594.236601443

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
61.342760531541394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,14S)-25-hydroxy-9,20-dimethoxy-15-methyl-7,23,33-trioxa-15lambda5,30-diazaoctacyclo[19.9.3.2^{3,6}.1^{8,12}.1^{14,18}.0^{24,32}.0^{27,31}.0^{22,34}]heptatriaconta-3,5,8,10,12(35),18(34),19,21,24(32),25,27(31),36-dodecaen-15-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.641251690064303

> <ALOGPS_LOGS>
-5.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.759038342468835

> <JCHEM_PKA_STRONGEST_BASIC>
8.874889282424702

> <JCHEM_POLAR_SURFACE_AREA>
105.29

> <JCHEM_REFRACTIVITY>
166.10209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,14S)-25-hydroxy-9,20-dimethoxy-15-methyl-7,23,33-trioxa-15lambda5,30-diazaoctacyclo[19.9.3.2^{3,6}.1^{8,12}.1^{14,18}.0^{24,32}.0^{27,31}.0^{22,34}]heptatriaconta-3,5,8,10,12(35),18(34),19,21,24(32),25,27(31),36-dodecaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.505  -4.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.665  -3.204   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.565  -1.902   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.125  -2.017   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.819  -3.435   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.012  -4.738   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.379  -3.663   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.216  -2.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.549  -0.909   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.014  -0.747   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.375   0.654   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.269   1.908   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.769  -2.403   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.505  -3.763   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      14.683  -5.082   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      16.123  -5.628   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.108  -5.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.591  -6.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.943  -8.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.370  -8.412   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.555  -9.791   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.485 -11.067   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.039 -10.981   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.742  -9.590   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.825 -12.458   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.699 -13.726   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.896 -10.023   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.268  -9.545   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.031  -8.269   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.185  -7.029   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.716  -6.401   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.547  -4.383   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.879  -2.597   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.072  -3.485   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.439  -4.909   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.532  -5.972   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.031  -5.957   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.938  -7.202   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.682  -5.105   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.740  -3.836   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       3.369  -2.441   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       3.923  -7.838   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.652  -9.262   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.427  -6.601   0.000  0.00  0.00           C+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   44                                             
CONECT   16   15                                                            
CONECT   17   15    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22   26                                                       
CONECT   26   25                                                            
CONECT   27   21   28                                                       
CONECT   28   27   29   43                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   42                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33    2   35                                                  
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36    1   38                                                  
CONECT   38   37                                                            
CONECT   39   35   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   33                                                       
CONECT   42   31   43                                                       
CONECT   43   42   28                                                       
CONECT   44   15                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₄N₂O₇

Average Mass

594.6640 Da

Monoisotopic Mass

594.23660 Da

IUPAC Name

(1R,14S)-25-hydroxy-9,20-dimethoxy-15-methyl-7,23,33-trioxa-15lambda5,30-diazaoctacyclo[19.9.3.2^{3,6}.1^{8,12}.1^{14,18}.0^{24,32}.0^{27,31}.0^{22,34}]heptatriaconta-3,5,8,10,12(35),18(34),19,21,24(32),25,27(31),36-dodecaen-15-one

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4=CC(OC5=CC=C(C[C@H]6NCCC7=C6C6=C(OC3=C1O6)C(O)=C7)C=C5)=C(OC)C=C4)N(C)(=O)CC2

InChI Identifier

InChI=1S/C35H34N2O7/c1-37(39)13-11-22-18-29(41-3)33-35-31(22)25(37)15-20-6-9-27(40-2)28(16-20)42-23-7-4-19(5-8-23)14-24-30-21(10-12-36-24)17-26(38)32(43-35)34(30)44-33/h4-9,16-18,24-25,36,38H,10-15H2,1-3H3/t24-,25+,37?/m1/s1

InChI Key

DJJSAIRLTRARJX-IRDRIFKTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Triclisia gilletii (De Wild.) Staner	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	2.98	ALOGPS
logP	3.64	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	166.1 m³·mol⁻¹	ChemAxon
Polarizability	61.34 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

163187973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Isogilletine N-oxide (NP0068051)

MOL for NP0068051 (Isogilletine N-oxide)

3D MOL for NP0068051 (Isogilletine N-oxide)

3D SDF for NP0068051 (Isogilletine N-oxide)

3D-SDF for NP0068051 (Isogilletine N-oxide)

PDB for NP0068051 (Isogilletine N-oxide)

3D PDB for NP0068051 (Isogilletine N-oxide)

SMILES for NP0068051 (Isogilletine N-oxide)

INCHI for NP0068051 (Isogilletine N-oxide)

Structure for NP0068051 (Isogilletine N-oxide)

3D Structure for NP0068051 (Isogilletine N-oxide)