NP-MRD: Showing NP-Card for N-Oxyhuperzine Q (NP0070235)

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Record Information

Version

2.0

Created at

2022-04-28 15:31:05 UTC

Updated at

2022-04-28 15:31:05 UTC

NP-MRD ID

NP0070235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Oxyhuperzine Q

Description

N-Oxyhuperzine Q belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. N-Oxyhuperzine Q is found in Huperzia serrata . Based on a literature review very few articles have been published on N-Oxyhuperzine Q.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
    0.9526   -2.7902    0.5607 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.1640   -1.5205    0.0459 N   0  0  2  0  0  4  0  0  0  0  0  0
    2.2736   -0.9988    0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1733    0.3322    1.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356    1.3702    0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346    1.5687   -0.0902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1977    2.3366    0.9940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0362    3.7242    0.8411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259    2.0340    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6789    0.9114   -0.2986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6736   -0.0756    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -1.2043    0.9736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8482   -2.3431    0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -1.7382   -0.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096   -0.8900    0.1371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7815   -0.9880    1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638    0.4282   -0.5086 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0168    0.2008   -2.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -0.6936   -2.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -1.7799   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272   -1.6902    1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1195   -0.8968   -0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5165    0.3759    2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080    0.5433    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6496    1.1583   -0.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3065    2.3574    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633    2.3001   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463    2.0970    2.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    3.9327   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288    1.8001    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    2.9582    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0066    1.3596   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4945    0.4593    0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1969   -0.4948   -0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -1.5232    1.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618   -2.4824   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -3.2502    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -0.0920    2.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674   -1.9085    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1957    1.2071   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929   -0.1075   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9198   -1.1486   -3.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0539   -0.0898   -2.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305   -2.7281   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5265   -2.0209   -1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  6
 15 16  1  0
 15 17  1  0
 17 18  1  6
 18 19  1  0
 19 20  1  0
 20  2  1  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
 17 10  1  0
  6 17  1  0
 16 12  1  0
  2 15  1  0
  8 29  1  0
  7 28  1  1
  9 30  1  0
  9 31  1  0
 10 32  1  6
 11 33  1  0
 11 34  1  0
 12 35  1  1
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  6
M  CHG  2   1  -1   2   1
M  END


  Mrv1652304282217312D          

 20 24  0  0  1  0            999 V2000
    2.9650    1.1037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1605    0.2433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4873   -0.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6691   -0.0138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9578    0.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061    1.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998    1.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8590    2.1903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1588    1.7540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4819    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308    2.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    1.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2284    3.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8004    2.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7716    1.4863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3546    0.8687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9906    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1702    0.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.6698    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
  3  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
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  1  0  0  0
  8 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
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  6  0  0  0
 17 19  1  1  0  0  0
  7 20  1  6  0  0  0
  4 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0070235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C[C@@H]2C[C@H]3CO[C@]4(C3)[C@@]22CCCN4(=O)CCC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO3/c18-14-8-12-7-11-9-16(20-10-11)15(12)4-2-6-17(16,19)5-1-3-13(14)15/h11-14,18H,1-10H2/t11-,12+,13-,14+,15+,16-,17?/m1/s1

> <INCHI_KEY>
CMSCBHTZEMGWKJ-GJQMDRQHSA-N

> <FORMULA>
C16H25NO3

> <MOLECULAR_WEIGHT>
279.38

> <EXACT_MASS>
279.183443669

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.084290051704542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,10S,11S,13S,15R)-11-hydroxy-17-oxa-6lambda5-azapentacyclo[13.2.1.0^{1,6}.0^{2,10}.0^{2,13}]octadecan-6-one

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.4678384866666675

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.914203578631469

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1694641939723653

> <JCHEM_POLAR_SURFACE_AREA>
56.34

> <JCHEM_REFRACTIVITY>
75.6121

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,10S,11S,13S,15R)-11-hydroxy-17-oxa-6lambda5-azapentacyclo[13.2.1.0^{1,6}.0^{2,10}.0^{2,13}]octadecan-6-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       5.535   2.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.900   0.454   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.643  -0.562   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.116  -0.026   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.788   0.903   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.251   2.453   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.920   2.562   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.470   4.089   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       2.163   3.274   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.633   4.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.031   4.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.267   3.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.160   5.611   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.829   5.737   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.094   4.491   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.040   2.774   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.129   1.622   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.449   0.231   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.651   1.853   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.602   1.250   0.000  0.00  0.00           C+0
CONECT    1    2    7   12   16                                             
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1    8   20                                             
CONECT    8    7    9   10   13                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1                                                       
CONECT   13    8   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    1   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17    2                                                       
CONECT   19   17                                                            
CONECT   20    7    4                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₅NO₃

Average Mass

279.3800 Da

Monoisotopic Mass

279.18344 Da

IUPAC Name

(1R,2S,10S,11S,13S,15R)-11-hydroxy-17-oxa-6lambda5-azapentacyclo[13.2.1.0^{1,6}.0^{2,10}.0^{2,13}]octadecan-6-one

Traditional Name

(1R,2S,10S,11S,13S,15R)-11-hydroxy-17-oxa-6lambda5-azapentacyclo[13.2.1.0^{1,6}.0^{2,10}.0^{2,13}]octadecan-6-one

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@@H]2C[C@H]3CO[C@]4(C3)[C@@]22CCCN4(=O)CCC[C@H]12

InChI Identifier

InChI=1S/C16H25NO3/c18-14-8-12-7-11-9-16(20-10-11)15(12)4-2-6-17(16,19)5-1-3-13(14)15/h11-14,18H,1-10H2/t11-,12+,13-,14+,15+,16-,17?/m1/s1

InChI Key

CMSCBHTZEMGWKJ-GJQMDRQHSA-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
Huperzia serrata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Quinolidine
Azepane
Oxepane
Piperidine
Cyclic alcohol
Trialkyl amine oxide
Tetrahydrofuran
Hemiaminal
Secondary alcohol
Trisubstituted n-oxide
Oxacycle
N-oxide
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic zwitterion
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	0.13	ALOGPS
logP	0.47	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.61 m³·mol⁻¹	ChemAxon
Polarizability	30.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00028738

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

15549049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for N-Oxyhuperzine Q (NP0070235)

MOL for NP0070235 (N-Oxyhuperzine Q)

3D MOL for NP0070235 (N-Oxyhuperzine Q)

3D SDF for NP0070235 (N-Oxyhuperzine Q)

3D-SDF for NP0070235 (N-Oxyhuperzine Q)

PDB for NP0070235 (N-Oxyhuperzine Q)

3D PDB for NP0070235 (N-Oxyhuperzine Q)

SMILES for NP0070235 (N-Oxyhuperzine Q)

INCHI for NP0070235 (N-Oxyhuperzine Q)

Structure for NP0070235 (N-Oxyhuperzine Q)

3D Structure for NP0070235 (N-Oxyhuperzine Q)