NP-MRD: Showing NP-Card for Thebaine (NP0137360)

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Record Information

Version

2.0

Created at

2022-05-30 16:50:05 UTC

Updated at

2022-05-30 16:50:05 UTC

NP-MRD ID

NP0137360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thebaine

Description

(-)-Thebaine belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic (-)-Thebaine is a very strong basic compound (based on its pKa). Thebaine is found in Papaver bracteatum, Papaver orientale, Papaver pseudo-orientale and Papaver somniferum. Minor constituent of opium.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
    1.4418    4.6998    0.9963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668    4.0047   -0.1654 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    2.7993    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419    2.9380    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804    1.7809    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073    0.5567    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722   -0.7176    0.9669 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1751   -1.8967    1.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501   -1.8010    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0776   -2.8341    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568   -2.6326    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6785   -1.3949   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9187   -1.1838   -1.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041   -2.1905   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -0.3484   -0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5744   -0.6876    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071    0.4705   -0.2111 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9834    0.3664   -1.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4313    0.0294   -1.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6421   -1.0335   -0.3844 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9969   -1.4497   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995    1.5148   -0.1071 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6595    1.0016   -1.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619    4.9632    1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9436    5.6110    0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    3.9922    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2866    3.9432    0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7415    1.8706    1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8877   -0.6819    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6984   -2.8024    0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410   -2.0800    2.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -3.7864    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -3.4109    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -2.6327   -0.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9012   -1.8243   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818   -3.0397   -1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262    1.2997   -2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947   -0.4303   -2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -0.3387   -2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0320    0.9382   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259   -1.3762    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6558   -0.9085   -0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -2.5509   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917    1.2530    0.9230 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 23  1  0
 23 22  1  0
 22 17  1  0
 17 18  1  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 15 12  2  0
 12 13  1  0
 13 14  1  0
 12 11  1  0
 11 10  2  0
 22  3  1  0
 17  6  1  0
 20  7  1  0
 10  9  1  0
 17 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  1
  8 30  1  0
  8 31  1  0
 22 44  1  1
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 11 33  1  0
 10 32  1  0
M  END


  Mrv0541 05061304452D          

 23 27  0  0  0  0            999 V2000
    0.8600    0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8378    3.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832    3.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4320    1.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890    1.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869    1.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341    1.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145   -1.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    0.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2480    0.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1349    2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1861    2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3279    2.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9931    2.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2480    1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371   -0.4502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3898    3.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9311    3.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605    2.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1578    0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 15 10  2  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 19 12  1  0  0  0  0
 20  2  1  0  0  0  0
 20 13  1  0  0  0  0
 21  3  1  0  0  0  0
 21 14  1  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
 18 23  1  0  0  0  0
 23  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3

> <INCHI_KEY>
FQXXSQDCDRQNQE-UHFFFAOYSA-N

> <FORMULA>
C19H21NO3

> <MOLECULAR_WEIGHT>
311.3749

> <EXACT_MASS>
311.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.84692179941753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
1.5322096289999991

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.380912852794788

> <JCHEM_POLAR_SURFACE_AREA>
30.930000000000003

> <JCHEM_REFRACTIVITY>
90.65969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.605   0.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.164   7.306   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.769   7.306   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.273   2.088   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.659   2.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.749   3.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.184   3.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.827  -2.380   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.736   0.245   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.767   1.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.166   1.768   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.196   0.245   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.718   4.697   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.214   4.697   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.736   2.912   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.212   4.377   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.720   4.377   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.196   2.912   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.869  -0.840   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       8.194   6.162   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.738   6.162   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.966   5.282   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.161   1.689   0.000  0.00  0.00           C+0
CONECT    1   19   23                                                       
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    6   10                                                       
CONECT    5    7   11                                                       
CONECT    6    4   13                                                       
CONECT    7    5   14                                                       
CONECT    8   19                                                            
CONECT    9   10   12                                                       
CONECT   10    4    9   15                                                  
CONECT   11    5   12   18                                                  
CONECT   12    9   11   19                                                  
CONECT   13    6   16   20                                                  
CONECT   14    7   17   21                                                  
CONECT   15   10   16   18                                                  
CONECT   16   13   15   22                                                  
CONECT   17   14   18   22                                                  
CONECT   18   11   15   17   23                                             
CONECT   19    1    8   12                                                  
CONECT   20    2   13                                                       
CONECT   21    3   14                                                       
CONECT   22   16   17                                                       
CONECT   23   18    1                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₃

Average Mass

311.3749 Da

Monoisotopic Mass

311.15214 Da

IUPAC Name

10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene

Traditional Name

10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaene

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4

InChI Identifier

InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3

InChI Key

FQXXSQDCDRQNQE-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
Papaver bracteatum	LOTUS Database	35616633
Papaver orientale	LOTUS Database	35616633
Papaver pseudo-orientale	LOTUS Database	35616633
Papaver somniferum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Tetralin
Coumaran
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Oxacycle
Ether
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.68	ALOGPS
logP	1.53	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.66 m³·mol⁻¹	ChemAxon
Polarizability	33.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029378

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000454

KNApSAcK ID

Not Available

Chemspider ID

361110

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

408120

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Thebaine (NP0137360)

MOL for NP0137360 (Thebaine)

3D MOL for NP0137360 (Thebaine)

3D SDF for NP0137360 (Thebaine)

3D-SDF for NP0137360 (Thebaine)

PDB for NP0137360 (Thebaine)

3D PDB for NP0137360 (Thebaine)

SMILES for NP0137360 (Thebaine)

INCHI for NP0137360 (Thebaine)

Structure for NP0137360 (Thebaine)

3D Structure for NP0137360 (Thebaine)