NP-MRD: Showing NP-Card for Thebaine N-oxide (NP0070523)

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Record Information

Version

2.0

Created at

2022-04-28 15:55:00 UTC

Updated at

2022-04-28 15:55:00 UTC

NP-MRD ID

NP0070523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thebaine N-oxide

Description

Thebaine N-oxide is found in Papaver bracteatum .

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
    0.1378    5.1827   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    3.9509   -0.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1342    2.7327   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    2.5911   -1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    1.3348   -1.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3035    0.3501   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9812   -0.9626   -0.7974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0221   -2.1444   -0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3994   -1.7064   -0.5971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -2.5011   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7787   -2.0561   -0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -0.8037   -0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2968   -0.3343   -0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4383   -1.0743   -0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -0.0017    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7265   -0.5117   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322    0.4161    0.4092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8692   -0.1356    1.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0203   -1.0506    1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176   -0.9979    0.4209 N   0  0  2  0  0  4  0  0  0  0  0  0
   -3.7176   -2.1045    0.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412    0.1460    0.4064 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.4353    1.6588    0.5875 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8331    1.2946    0.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419    5.2568    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686    5.3904   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9346    5.9633   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9905    3.4041   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    1.2968   -2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872   -0.9955   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -2.6858   -1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321   -2.8647    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945   -3.4787   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6100   -2.6814   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3407   -0.4346   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199   -1.4948   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6341   -1.9427    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215   -0.7059    2.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0239    0.7258    2.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7239   -0.7826    2.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486   -2.1211    1.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2500   -3.0899    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2527   -2.0579   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4952   -1.9971    1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2273    2.0228    1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 16  2  0
 16 15  1  0
 15 24  1  0
 24 23  1  0
 23 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  1
 15 12  2  0
 12 13  1  0
 13 14  1  0
 12 11  1  0
 11 10  2  0
 23  3  1  0
 17  6  1  0
 20  7  1  0
 10  9  1  0
 17 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  6
  8 31  1  0
  8 32  1  0
 23 45  1  1
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 11 34  1  0
 10 33  1  0
M  CHG  2  20   1  22  -1
M  END


  Mrv1652304282217552D          

 24 28  0  0  1  0            999 V2000
    2.5695    2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964    1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402    0.8616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2953    1.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5195    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8403   -0.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376    0.0227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4432   -0.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9138    0.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9546    1.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    2.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2934    0.1795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -1.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3089   -1.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610    2.2154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8717    2.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2182    1.9536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293    2.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218    1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7864    0.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038    2.0237    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  1  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  1 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18  4  1  6  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 20 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2[C@H]3CC4=C5C(O[C@@H]1[C@@]25CCN3(C)=O)=C(OC)C=C4

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO4/c1-20(21)9-8-19-12-5-7-15(23-3)18(19)24-17-14(22-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13?,18-,19-,20?/m0/s1

> <INCHI_KEY>
PMXUJDPQAVEYII-LEVRYPNCSA-N

> <FORMULA>
C19H21NO4

> <MOLECULAR_WEIGHT>
327.38

> <EXACT_MASS>
327.14705816

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.381924033802136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R)-10,14-dimethoxy-4-methyl-12-oxa-4lambda5-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,14,16-pentaen-4-one

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
0.40783444566666616

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.1083951151376086

> <JCHEM_POLAR_SURFACE_AREA>
54.57

> <JCHEM_REFRACTIVITY>
92.7046

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,13R)-10,14-dimethoxy-4-methyl-12-oxa-4lambda5-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,14,16-pentaen-4-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       4.796   3.748   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.473   2.189   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.062   1.608   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.418   2.737   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.970   2.177   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.377   0.557   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.569  -0.478   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.057   0.042   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.561  -0.334   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.439   0.992   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.930   1.429   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.382   2.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.323   4.060   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.014   0.335   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.504   0.727   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.278  -1.990   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.443  -2.998   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.981   4.135   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.494   4.714   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.407   3.647   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       0.241   5.178   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.041   2.079   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.468   1.135   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.127   3.778   0.000  0.00  0.00           C+0
CONECT    1    2   13   19                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4    8   23                                             
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    1                                                       
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16    7   17                                                       
CONECT   17   16                                                            
CONECT   18    4   19   20                                                  
CONECT   19   18    1                                                       
CONECT   20   18   21   22   24                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    3                                                       
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₄

Average Mass

327.3800 Da

Monoisotopic Mass

327.14706 Da

IUPAC Name

(1S,5R,13R)-10,14-dimethoxy-4-methyl-12-oxa-4lambda5-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,14,16-pentaen-4-one

Traditional Name

(1S,5R,13R)-10,14-dimethoxy-4-methyl-12-oxa-4lambda5-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,14,16-pentaen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2[C@H]3CC4=C5C(O[C@@H]1[C@@]25CCN3(C)=O)=C(OC)C=C4

InChI Identifier

InChI=1S/C19H21NO4/c1-20(21)9-8-19-12-5-7-15(23-3)18(19)24-17-14(22-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13?,18-,19-,20?/m0/s1

InChI Key

PMXUJDPQAVEYII-LEVRYPNCSA-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
Papaver bracteatum	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	1.06	ALOGPS
logP	0.41	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	2.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	54.57 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.7 m³·mol⁻¹	ChemAxon
Polarizability	34.38 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

Not Available

References

General References

Not Available

Showing NP-Card for Thebaine N-oxide (NP0070523)

MOL for NP0070523 (Thebaine N-oxide)

3D MOL for NP0070523 (Thebaine N-oxide)

3D SDF for NP0070523 (Thebaine N-oxide)

3D-SDF for NP0070523 (Thebaine N-oxide)

PDB for NP0070523 (Thebaine N-oxide)

3D PDB for NP0070523 (Thebaine N-oxide)

SMILES for NP0070523 (Thebaine N-oxide)

INCHI for NP0070523 (Thebaine N-oxide)

Structure for NP0070523 (Thebaine N-oxide)

3D Structure for NP0070523 (Thebaine N-oxide)