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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:38:56 UTC

Update Date

2022-11-23 22:13:43 UTC

HMDB ID

HMDB0253279

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hydroxymorphinan

Description

Hydroxymorphinan 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. Based on a literature review a significant number of articles have been published on Hydroxymorphinan. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hydroxymorphinan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hydroxymorphinan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253279
     RDKit          3D
hydroxymorphinan
 39 42  0  0  0  0  0  0  0  0999 V2000
    3.4427    0.0932    2.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    0.4899    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    1.3665    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    1.7633   -1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948    1.2921   -1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030    0.4190   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    0.0187    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -0.9336    1.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3432   -1.6028    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0413   -2.6321    0.2457 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3312   -2.5609   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3913   -1.2107   -1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -0.0774   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531    1.0521   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    1.2263   -0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000    1.6057    0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6857    0.4636    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -0.6085    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3688    0.4400    2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3653    1.7393    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.4550   -1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097    1.6512   -2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -1.7493    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684   -0.4138    2.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668   -2.0530    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488   -3.0907    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4021   -3.1752   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072   -3.1097   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.1771   -2.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -1.0318   -2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551    0.8190   -2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8409    2.0347   -1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    0.3113   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1876    2.0943   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3613    1.8222    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    2.5094    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    0.8597    2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596    0.0509    2.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.1508    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7  2  1  0
 18  9  1  0
 13  6  1  0
 18 13  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
M  END

  Mrv1652309112113392D          

 18 21  0  0  0  0            999 V2000
    3.1752   -0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273    1.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706    0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5231   -0.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1590   -1.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7482    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -0.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803   -1.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -0.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279    0.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001    0.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504    0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -1.6177    0.0000 O   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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253279

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC2=C1CC1NCCC22CCCCC12

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO/c18-15-6-3-5-12-11(15)10-14-13-4-1-2-7-16(12,13)8-9-17-14/h3,5-6,13-14,17-18H,1-2,4,7-10H2

> <INCHI_KEY>
SVZZBABSMGVXHM-UHFFFAOYSA-N

> <FORMULA>
C16H21NO

> <MOLECULAR_WEIGHT>
243.35

> <EXACT_MASS>
243.1623143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.53755170550165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-6-ol

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.545972239171042

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.420892915755065

> <JCHEM_PKA_STRONGEST_BASIC>
9.60516658728841

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
72.78620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0253279
     RDKit          3D
hydroxymorphinan
 39 42  0  0  0  0  0  0  0  0999 V2000
    3.4427    0.0932    2.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    0.4899    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    1.3665    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    1.7633   -1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948    1.2921   -1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030    0.4190   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    0.0187    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -0.9336    1.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3432   -1.6028    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0413   -2.6321    0.2457 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3312   -2.5609   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3913   -1.2107   -1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -0.0774   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531    1.0521   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    1.2263   -0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000    1.6057    0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6857    0.4636    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -0.6085    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3688    0.4400    2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3653    1.7393    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.4550   -1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097    1.6512   -2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -1.7493    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684   -0.4138    2.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668   -2.0530    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488   -3.0907    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4021   -3.1752   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072   -3.1097   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.1771   -2.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -1.0318   -2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551    0.8190   -2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8409    2.0347   -1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    0.3113   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1876    2.0943   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3613    1.8222    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    2.5094    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    0.8597    2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596    0.0509    2.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.1508    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7  2  1  0
 18  9  1  0
 13  6  1  0
 18 13  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       5.927  -0.011   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.442   1.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.718   2.366   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.345   1.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.812   1.522   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.831   0.335   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.976  -1.198   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.164  -2.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.263   0.130   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.513  -0.276   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.697  -2.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.678  -0.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.532   0.687   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.787   1.580   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.187   0.939   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.333  -0.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.078  -1.487   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.224  -3.020   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9   13                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9    1                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

COMPND    HMDB0253279
HETATM    1  O1  UNL     1       3.443   0.093   2.103  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.757   0.490   0.969  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.352   1.366   0.106  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.673   1.763  -1.023  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.395   1.292  -1.305  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.803   0.419  -0.444  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.468   0.019   0.679  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.901  -0.934   1.674  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.343  -1.603   1.129  1.00  0.00           C  
HETATM   10  N1  UNL     1       0.041  -2.632   0.246  1.00  0.00           N  
HETATM   11  C9  UNL     1      -0.331  -2.561  -1.101  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.391  -1.211  -1.732  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.544  -0.077  -0.740  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.353   1.052  -1.353  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.686   1.226  -0.660  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.400   1.606   0.766  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.686   0.464   1.422  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.269  -0.608   0.471  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.369   0.440   2.298  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.365   1.739   0.330  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.140   2.455  -1.707  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.910   1.651  -2.228  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.616  -1.749   1.919  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.668  -0.414   2.619  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.867  -2.053   2.004  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.949  -3.091   0.465  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.402  -3.175  -1.699  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.307  -3.110  -1.237  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.280  -1.177  -2.398  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.483  -1.032  -2.394  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.555   0.819  -2.410  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.841   2.035  -1.272  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.266   0.311  -0.745  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.188   2.094  -1.134  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.361   1.822   1.251  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.759   2.509   0.801  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.801   0.860   2.003  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.360   0.051   2.203  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.148  -1.151   0.127  1.00  0.00           H  
CONECT    1    2   19
CONECT    2    3    3    7
CONECT    3    4   20
CONECT    4    5    5   21
CONECT    5    6   22
CONECT    6    7    7   13
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   18   25
CONECT   10   11   26
CONECT   11   12   27   28
CONECT   12   13   29   30
CONECT   13   14   18
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   18   37   38
CONECT   18   39
END

HMDB0253279
     RDKit          3D
hydroxymorphinan
 39 42  0  0  0  0  0  0  0  0999 V2000
    3.4427    0.0932    2.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    0.4899    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    1.3665    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    1.7633   -1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948    1.2921   -1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030    0.4190   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    0.0187    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -0.9336    1.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3432   -1.6028    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0413   -2.6321    0.2457 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3312   -2.5609   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3913   -1.2107   -1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -0.0774   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531    1.0521   -1.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6857    1.2263   -0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000    1.6057    0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6857    0.4636    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -0.6085    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3688    0.4400    2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3653    1.7393    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400    2.4550   -1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097    1.6512   -2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -1.7493    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684   -0.4138    2.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668   -2.0530    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488   -3.0907    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4021   -3.1752   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072   -3.1097   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.1771   -2.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -1.0318   -2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551    0.8190   -2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8409    2.0347   -1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    0.3113   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1876    2.0943   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3613    1.8222    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    2.5094    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    0.8597    2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596    0.0509    2.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.1508    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7  2  1  0
 18  9  1  0
 13  6  1  0
 18 13  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁NO

Average Molecular Weight

243.35

Monoisotopic Molecular Weight

243.1623143

IUPAC Name

17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-6-ol

Traditional Name

17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-6-ol

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C1CC1NCCC22CCCCC12

InChI Identifier

InChI=1S/C16H21NO/c18-15-6-3-5-12-11(15)10-14-13-4-1-2-7-16(12,13)8-9-17-14/h3,5-6,13-14,17-18H,1-2,4,7-10H2

InChI Key

SVZZBABSMGVXHM-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
Benzazocine
Tetralin
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Piperidine
Benzenoid
Secondary aliphatic amine
Azacycle
Secondary amine
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
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)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.65	ALOGPS
logP	2.55	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.42	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.79 m³·mol⁻¹	ChemAxon
Polarizability	27.54 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	185.075	30932474
DeepCCS	[M+Na]+	159.813	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
hydroxymorphinan	OC1=CC=CC2=C1CC1NCCC22CCCCC12	3177.0	Standard polar	33892256
hydroxymorphinan	OC1=CC=CC2=C1CC1NCCC22CCCCC12	2231.7	Standard non polar	33892256
hydroxymorphinan	OC1=CC=CC2=C1CC1NCCC22CCCCC12	2281.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
hydroxymorphinan,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1CC1C3CCCCC23CCN1[Si](C)(C)C	2280.4	Semi standard non polar	33892256
hydroxymorphinan,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1CC1C3CCCCC23CCN1[Si](C)(C)C	2401.9	Standard non polar	33892256
hydroxymorphinan,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1CC1C3CCCCC23CCN1[Si](C)(C)C	2693.1	Standard polar	33892256
hydroxymorphinan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1CC1C3CCCCC23CCN1[Si](C)(C)C(C)(C)C	2736.0	Semi standard non polar	33892256
hydroxymorphinan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1CC1C3CCCCC23CCN1[Si](C)(C)C(C)(C)C	2912.0	Standard non polar	33892256
hydroxymorphinan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1CC1C3CCCCC23CCN1[Si](C)(C)C(C)(C)C	2976.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxymorphinan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0wmi-1290000000-ca62ddb32367b88ab336	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxymorphinan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxymorphinan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxymorphinan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxymorphinan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxymorphinan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxymorphinan 10V, Positive-QTOF	splash10-0006-0090000000-cb3b647005f5e082dc2b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxymorphinan 20V, Positive-QTOF	splash10-0006-0090000000-09e50cd717cd7f4b05b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxymorphinan 40V, Positive-QTOF	splash10-0udm-1960000000-c95adaf9a72c6cfa3627	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxymorphinan 10V, Negative-QTOF	splash10-0006-0090000000-4e29b1857a321737d61e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxymorphinan 20V, Negative-QTOF	splash10-0006-0090000000-4e29b1857a321737d61e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxymorphinan 40V, Negative-QTOF	splash10-0006-0890000000-83a732206c0c79ea3536	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14637996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Hydroxymorphinan

METLIN ID

Not Available

PubChem Compound

19863490

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Hydroxymorphinan (HMDB0253279)

MOL for HMDB0253279 (Hydroxymorphinan)

3D MOL for HMDB0253279 (Hydroxymorphinan)

3D SDF for HMDB0253279 (Hydroxymorphinan)

3D-SDF for HMDB0253279 (Hydroxymorphinan)

PDB for HMDB0253279 (Hydroxymorphinan)

3D PDB for HMDB0253279 (Hydroxymorphinan)

SMILES for HMDB0253279 (Hydroxymorphinan)

INCHI for HMDB0253279 (Hydroxymorphinan)

Structure for HMDB0253279 (Hydroxymorphinan)

3D Structure for HMDB0253279 (Hydroxymorphinan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra