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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:04 UTC

Update Date

2022-03-07 02:52:08 UTC

HMDB ID

HMDB0029378

Secondary Accession Numbers

HMDB29378

Metabolite 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). Minor constituent of opium.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0258963
     RDKit          3D
THEBAINE
 44 48  0  0  0  0  0  0  0  0999 V2000
    2.4799    4.3657   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165    3.3665    0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9620    2.5132   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238    2.7427   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.8582   -1.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522    0.8360   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -0.1393   -0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -1.5919   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175   -1.7042   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297   -2.8073   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -2.8617   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -1.7891    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -1.7999    0.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -2.8659    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -0.6787    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -0.7211    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    0.5019    0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930    0.1313    1.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    0.4347    1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1479    0.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3843   -0.6891    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7573    1.3963    0.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281    0.5618    1.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243    4.9090   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    3.8526   -1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    5.0756   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    3.6151   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    2.0958   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    0.0262   -1.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -2.1165   -1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3082   -2.1442   -0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -3.6442   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810   -3.7358   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -3.6386    0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3821   -3.3244   -0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -2.4885    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023   -0.9380    1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.7089    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.1597    2.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356    1.4989    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739   -1.5033    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2752   -0.0443    0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5220   -1.0651   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898    1.8127    1.9068 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 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 22  3  1  0
 17  6  1  0
 20  7  1  0
 16  9  1  0
 23 15  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  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 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
 22 44  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>
HMDB0029378

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0258963
     RDKit          3D
THEBAINE
 44 48  0  0  0  0  0  0  0  0999 V2000
    2.4799    4.3657   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165    3.3665    0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9620    2.5132   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238    2.7427   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.8582   -1.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522    0.8360   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -0.1393   -0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -1.5919   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175   -1.7042   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297   -2.8073   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -2.8617   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -1.7891    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -1.7999    0.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -2.8659    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -0.6787    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -0.7211    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    0.5019    0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930    0.1313    1.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    0.4347    1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1479    0.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3843   -0.6891    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7573    1.3963    0.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281    0.5618    1.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243    4.9090   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    3.8526   -1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    5.0756   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    3.6151   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    2.0958   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    0.0262   -1.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -2.1165   -1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3082   -2.1442   -0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -3.6442   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810   -3.7358   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -3.6386    0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3821   -3.3244   -0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -2.4885    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023   -0.9380    1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.7089    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.1597    2.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356    1.4989    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739   -1.5033    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2752   -0.0443    0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5220   -1.0651   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898    1.8127    1.9068 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 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 22  3  1  0
 17  6  1  0
 20  7  1  0
 16  9  1  0
 23 15  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  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 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
 22 44  1  0
M  END

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

COMPND    HMDB0258963
HETATM    1  C1  UNL     1       2.480   4.366  -0.625  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.017   3.367   0.251  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.962   2.513  -0.044  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.224   2.743  -1.105  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.885   1.858  -1.430  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.152   0.836  -0.671  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.242  -0.139  -0.890  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.779  -1.592  -0.810  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.317  -1.704  -0.498  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.430  -2.807  -0.857  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.803  -2.862  -0.584  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.433  -1.789   0.061  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.771  -1.800   0.347  1.00  0.00           O  
HETATM   14  C12 UNL     1       4.642  -2.866   0.032  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.687  -0.679   0.424  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.365  -0.721   0.118  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.360   0.502   0.561  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.293   0.131   1.649  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.732   0.435   1.406  1.00  0.00           C  
HETATM   20  N1  UNL     1      -3.234   0.148   0.111  1.00  0.00           N  
HETATM   21  C18 UNL     1      -4.384  -0.689   0.058  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.757   1.396   0.885  1.00  0.00           C  
HETATM   23  O3  UNL     1       1.928   0.562   1.055  1.00  0.00           O  
HETATM   24  H1  UNL     1       3.324   4.909  -0.163  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.877   3.853  -1.527  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.702   5.076  -0.943  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.460   3.615  -1.743  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.460   2.096  -2.321  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.708   0.026  -1.882  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.925  -2.117  -1.778  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.308  -2.144  -0.029  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.012  -3.644  -1.350  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.381  -3.736  -0.871  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.511  -3.639   0.828  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.382  -3.324  -0.930  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.692  -2.488   0.005  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.202  -0.938   1.950  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.985   0.709   2.570  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.331  -0.160   2.146  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.936   1.499   1.647  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.374  -1.503   0.808  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.275  -0.044   0.311  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.522  -1.065  -0.974  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.590   1.813   1.907  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   17
CONECT    7    8   20   29
CONECT    8    9   30   31
CONECT    9   10   10   16
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13   15
CONECT   13   14
CONECT   14   34   35   36
CONECT   15   16   16   23
CONECT   16   17
CONECT   17   18   22
CONECT   18   19   37   38
CONECT   19   20   39   40
CONECT   20   21
CONECT   21   41   42   43
CONECT   22   23   44
END

HMDB0258963
     RDKit          3D
THEBAINE
 44 48  0  0  0  0  0  0  0  0999 V2000
    2.4799    4.3657   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165    3.3665    0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9620    2.5132   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238    2.7427   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.8582   -1.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522    0.8360   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -0.1393   -0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -1.5919   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175   -1.7042   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297   -2.8073   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -2.8617   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -1.7891    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -1.7999    0.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -2.8659    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -0.6787    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -0.7211    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    0.5019    0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930    0.1313    1.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    0.4347    1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1479    0.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3843   -0.6891    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7573    1.3963    0.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281    0.5618    1.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243    4.9090   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    3.8526   -1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    5.0756   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    3.6151   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    2.0958   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    0.0262   -1.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -2.1165   -1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3082   -2.1442   -0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -3.6442   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810   -3.7358   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -3.6386    0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3821   -3.3244   -0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -2.4885    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023   -0.9380    1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.7089    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.1597    2.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356    1.4989    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739   -1.5033    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2752   -0.0443    0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5220   -1.0651   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898    1.8127    1.9068 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 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 22  3  1  0
 17  6  1  0
 20  7  1  0
 16  9  1  0
 23 15  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  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 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
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₃

Average Molecular Weight

311.3749

Monoisotopic Molecular Weight

311.152143543

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.7 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.147	31661259
DarkChem	[M-H]-	168.562	31661259
DeepCCS	[M-2H]-	205.17	30932474
DeepCCS	[M+Na]+	180.397	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.2	32859911
AllCCS	[M+NH4]+	178.4	32859911
AllCCS	[M+Na]+	179.3	32859911
AllCCS	[M-H]-	182.2	32859911
AllCCS	[M+Na-2H]-	181.7	32859911
AllCCS	[M+HCOO]-	181.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Thebaine	COC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4	3961.1	Standard polar	33892256
(-)-Thebaine	COC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4	2534.0	Standard non polar	33892256
(-)-Thebaine	COC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4	2494.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6t-0090000000-f2d758bd9f2c7d25eee8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Thebaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOF	splash10-0bt9-8095000000-65e3965b2bd1c1efef99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOF	splash10-0a4i-6091000000-ffa57ed65751978e70f6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOF	splash10-0a4i-4190000000-cce3eceb7d285ca59050	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Thebaine LC-ESI-QQ , positive-QTOF	splash10-0a4i-7290000000-2c44d64ff75d058c2ac8	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Positive-QTOF	splash10-03di-0019000000-39a448b3d40ec9d12e71	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Positive-QTOF	splash10-03di-1059000000-2e0d89d0f18a3a84253e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Positive-QTOF	splash10-0ldl-3090000000-d1acc13f765f37b71b1c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Negative-QTOF	splash10-03di-0009000000-c7e246f79453d627a81c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Negative-QTOF	splash10-03di-1079000000-8b39f9d42c4e9db46d39	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Negative-QTOF	splash10-0lyc-1090000000-aea1036f1a7cc5883fae	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Positive-QTOF	splash10-03di-0009000000-9f3b29c8dcdf015b99e9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Positive-QTOF	splash10-03di-0009000000-9f3b29c8dcdf015b99e9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Positive-QTOF	splash10-03xr-2097000000-b498f59ba8b30aec4dad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 10V, Negative-QTOF	splash10-03di-0009000000-9bf675b2e28db05b0d3b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 20V, Negative-QTOF	splash10-03di-0019000000-e6e38b238d4d20f4464f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Thebaine 40V, Negative-QTOF	splash10-03di-0092000000-2709608ec08b22155ac4	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (-)-Thebaine (HMDB0029378)

MOL for HMDB0029378 ((-)-Thebaine)

3D MOL for HMDB0029378 ((-)-Thebaine)

3D SDF for HMDB0029378 ((-)-Thebaine)

3D-SDF for HMDB0029378 ((-)-Thebaine)

PDB for HMDB0029378 ((-)-Thebaine)

3D PDB for HMDB0029378 ((-)-Thebaine)

SMILES for HMDB0029378 ((-)-Thebaine)

INCHI for HMDB0029378 ((-)-Thebaine)

Structure for HMDB0029378 ((-)-Thebaine)

3D Structure for HMDB0029378 ((-)-Thebaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra