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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:00:06 UTC

Update Date

2021-09-14 15:45:57 UTC

HMDB ID

HMDB0060796

Secondary Accession Numbers

HMDB60796

Metabolite Identification

Common Name

6alpha-Hydroxy-hydromorphone

Description

6alpha-Hydroxy-hydromorphone is a metabolite of hydromorphone. Hydromorphone, a more common synonym for dihydromorphinone, commonly a hydrochloride (brand names Palladone, Dilaudid, and numerous others) is a very potent centrally acting analgesic drug of the opioid class. It is a derivative of morphine, to be specific, a hydrogenated ketone thereof and, therefore, a semi-synthetic drug. It is, in medical terms, an opioid analgesic and, in legal terms, a narcotic. (Wikipedia)

Structure

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

HMDB0060796
     RDKit          3D
6alpha-Hydroxy-hydromorphone
 42 46  0  0  0  0  0  0  0  0999 V2000
    3.7527   -0.2015    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056   -0.6673   -0.0868 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -0.6161   -1.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -0.3883   -1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911   -0.3046   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980    1.0737   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    1.9345    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288    3.2085    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    3.5398    0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658    2.5933   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    2.9286   -0.3964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    1.3101   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    0.1167   -0.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -0.9448   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1071   -1.8920    0.4160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2034   -2.6661    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -2.7877    0.9032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -2.2225    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569   -0.7432    0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5683   -0.0498    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.4514    0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -0.9516   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    0.7750   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582   -0.0630    1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743    0.1343   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192   -1.5941   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.5768   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -1.1537   -2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786    3.9316    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809    4.5519    0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2425    3.8501   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -1.5008   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775   -1.3068    1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9474   -3.0281   -0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -3.0541    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -3.7423    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -2.6842    1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -2.5111   -0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -0.4335    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931   -0.1880    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    1.6973   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558    2.0214    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 14  5  1  0
 19  5  1  0
 12  6  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END


  Mrv0541 07041312002D          

 21 25  0  0  1  0            999 V2000
   -1.2648    1.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7004    0.4527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -0.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465   -0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054   -0.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5263   -1.6716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9729   -0.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7567   -0.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3366   -1.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756    0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4009    0.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6011    0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190    0.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3733   -0.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968   -0.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282   -1.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046   -1.7294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2841   -2.5205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478   -0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  1  0  0  0
 13 21  2  0  0  0  0
  5 21  1  0  0  0  0
  8 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060796

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC23C4OC5=C(O)C=CC(CC1C2CC[C@@H]4O)=C35

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10?,11?,13-,16?,17?/m0/s1

> <INCHI_KEY>
IJVCSMSMFSCRME-LIBMUZAMSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.63370943121493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(14S)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-triene-10,14-diol

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.0786493941262503

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.151856484300978

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.28893176965798

> <JCHEM_PKA_STRONGEST_BASIC>
9.235781522934598

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
79.15979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(14S)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-triene-10,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060796
     RDKit          3D
6alpha-Hydroxy-hydromorphone
 42 46  0  0  0  0  0  0  0  0999 V2000
    3.7527   -0.2015    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056   -0.6673   -0.0868 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -0.6161   -1.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -0.3883   -1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911   -0.3046   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980    1.0737   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    1.9345    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288    3.2085    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    3.5398    0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658    2.5933   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    2.9286   -0.3964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    1.3101   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    0.1167   -0.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -0.9448   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1071   -1.8920    0.4160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2034   -2.6661    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -2.7877    0.9032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -2.2225    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569   -0.7432    0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5683   -0.0498    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.4514    0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -0.9516   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    0.7750   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582   -0.0630    1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743    0.1343   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192   -1.5941   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.5768   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -1.1537   -2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786    3.9316    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809    4.5519    0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2425    3.8501   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -1.5008   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775   -1.3068    1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9474   -3.0281   -0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -3.0541    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -3.7423    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -2.6842    1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -2.5111   -0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -0.4335    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931   -0.1880    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    1.6973   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558    2.0214    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 14  5  1  0
 19  5  1  0
 12  6  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      -2.361   1.932   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.307   0.845   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.750  -0.673   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.273  -1.652   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.317  -1.245   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.325  -2.785   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.849  -3.120   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.683  -1.804   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.146  -1.364   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.228  -2.422   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.554   0.113   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.482   1.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.989   0.885   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.715   1.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.255   1.247   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.697  -0.145   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.741  -0.625   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.359  -2.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.195  -3.228   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.530  -4.705   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.703  -0.655   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16   21                                             
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14    2   16                                                  
CONECT   16   15    5   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    6   20                                                  
CONECT   20   19                                                            
CONECT   21   13    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0060796
HETATM    1  C1  UNL     1       3.753  -0.201   0.060  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.406  -0.667  -0.087  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.932  -0.616  -1.417  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.499  -0.388  -1.636  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.391  -0.305  -0.464  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.798   1.074  -0.139  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.133   1.935   0.355  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.329   3.209   0.605  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.671   3.540   0.353  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.566   2.593  -0.153  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.882   2.929  -0.396  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.104   1.310  -0.406  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.679   0.117  -0.891  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.734  -0.945  -0.644  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.107  -1.892   0.416  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.203  -2.666   0.009  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.017  -2.788   0.903  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.378  -2.222   0.729  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.257  -0.743   0.855  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.568  -0.050   0.901  1.00  0.00           C  
HETATM   21  C17 UNL     1       1.529   1.451   0.636  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.510  -0.952  -0.295  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.942   0.775  -0.418  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.958  -0.063   1.147  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.574   0.134  -1.970  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.219  -1.594  -1.910  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.381   0.577  -2.216  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.055  -1.154  -2.341  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.379   3.932   0.999  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.981   4.552   0.566  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.242   3.850  -0.222  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.694  -1.501  -1.627  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.477  -1.307   1.304  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.947  -3.028  -0.888  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.113  -3.054   1.977  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.048  -3.742   0.339  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.054  -2.684   1.470  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.734  -2.511  -0.263  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.440  -0.434   1.668  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.093  -0.188   1.889  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.115   1.697  -0.270  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.956   2.021   1.473  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   14   19
CONECT    6    7    7   12
CONECT    7    8   21
CONECT    8    9    9   29
CONECT    9   10   30
CONECT   10   11   12   12
CONECT   11   31
CONECT   12   13
CONECT   13   14
CONECT   14   15   32
CONECT   15   16   17   33
CONECT   16   34
CONECT   17   18   35   36
CONECT   18   19   37   38
CONECT   19   20   39
CONECT   20   21   40
CONECT   21   41   42
END

HMDB0060796
     RDKit          3D
6alpha-Hydroxy-hydromorphone
 42 46  0  0  0  0  0  0  0  0999 V2000
    3.7527   -0.2015    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056   -0.6673   -0.0868 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -0.6161   -1.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -0.3883   -1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911   -0.3046   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980    1.0737   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    1.9345    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288    3.2085    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706    3.5398    0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658    2.5933   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    2.9286   -0.3964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    1.3101   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    0.1167   -0.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -0.9448   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1071   -1.8920    0.4160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2034   -2.6661    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -2.7877    0.9032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -2.2225    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569   -0.7432    0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5683   -0.0498    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.4514    0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -0.9516   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    0.7750   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582   -0.0630    1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743    0.1343   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192   -1.5941   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.5768   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -1.1537   -2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786    3.9316    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809    4.5519    0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2425    3.8501   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -1.5008   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775   -1.3068    1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9474   -3.0281   -0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -3.0541    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -3.7423    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -2.6842    1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -2.5111   -0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -0.4335    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931   -0.1880    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    1.6973   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558    2.0214    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 14  5  1  0
 19  5  1  0
 12  6  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6a-Hydroxy-hydromorphone	Generator
6Α-hydroxy-hydromorphone	Generator

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

(14S)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-triene-10,14-diol

Traditional Name

(14S)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-triene-10,14-diol

CAS Registry Number

Not Available

SMILES

CN1CCC23C4OC5=C(O)C=CC(CC1C2CC[C@@H]4O)=C35

InChI Identifier

InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10?,11?,13-,16?,17?/m0/s1

InChI Key

IJVCSMSMFSCRME-LIBMUZAMSA-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
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Cyclic alcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Alcohol
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 (HMDB: HMDB0060796)

Organ

Kidney (HMDB: HMDB0060796)
Liver (HMDB: HMDB0060796)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060796)

Cellular substructure

Cytoplasm (HMDB: HMDB0060796)

Source

Endogenous

Endogenous (HMDB: HMDB0060796)

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
Water Solubility	1.82 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.08	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.93 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.16 m³·mol⁻¹	ChemAxon
Polarizability	30.63 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.514	31661259
DarkChem	[M-H]-	160.326	31661259
DeepCCS	[M-2H]-	199.205	30932474
DeepCCS	[M+Na]+	175.346	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.5	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	174.6	32859911
AllCCS	[M+Na-2H]-	174.0	32859911
AllCCS	[M+HCOO]-	173.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.81 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8323 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1054.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	299.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	313.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	583.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	697.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	250.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	946.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	526.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	464.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	130.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6alpha-Hydroxy-hydromorphone	CN1CCC23C4OC5=C(O)C=CC(CC1C2CC[C@@H]4O)=C35	3755.0	Standard polar	33892256
6alpha-Hydroxy-hydromorphone	CN1CCC23C4OC5=C(O)C=CC(CC1C2CC[C@@H]4O)=C35	2429.2	Standard non polar	33892256
6alpha-Hydroxy-hydromorphone	CN1CCC23C4OC5=C(O)C=CC(CC1C2CC[C@@H]4O)=C35	2478.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6alpha-Hydroxy-hydromorphone,1TMS,isomer #1	CN1CCC23C4=C5C=CC(O[Si](C)(C)C)=C4OC2[C@@H](O)CCC3C1C5	2476.8	Semi standard non polar	33892256
6alpha-Hydroxy-hydromorphone,1TMS,isomer #2	CN1CCC23C4=C5C=CC(O)=C4OC2[C@@H](O[Si](C)(C)C)CCC3C1C5	2433.9	Semi standard non polar	33892256
6alpha-Hydroxy-hydromorphone,2TMS,isomer #1	CN1CCC23C4=C5C=CC(O[Si](C)(C)C)=C4OC2[C@@H](O[Si](C)(C)C)CCC3C1C5	2478.7	Semi standard non polar	33892256
6alpha-Hydroxy-hydromorphone,1TBDMS,isomer #1	CN1CCC23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4OC2[C@@H](O)CCC3C1C5	2749.3	Semi standard non polar	33892256
6alpha-Hydroxy-hydromorphone,1TBDMS,isomer #2	CN1CCC23C4=C5C=CC(O)=C4OC2[C@@H](O[Si](C)(C)C(C)(C)C)CCC3C1C5	2678.1	Semi standard non polar	33892256
6alpha-Hydroxy-hydromorphone,2TBDMS,isomer #1	CN1CCC23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4OC2[C@@H](O[Si](C)(C)C(C)(C)C)CCC3C1C5	2919.6	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 - 6alpha-Hydroxy-hydromorphone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1090000000-3f5cd161c87911407205	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxy-hydromorphone GC-MS (2 TMS) - 70eV, Positive	splash10-01di-6309700000-61de6f13f6659db9e236	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxy-hydromorphone 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 10V, Positive-QTOF	splash10-000i-0090000000-2a28cd85a2b98efeb266	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 20V, Positive-QTOF	splash10-000i-0090000000-dab26b961468c015c5b1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 40V, Positive-QTOF	splash10-0fdo-5090000000-5018a361bd08eac2ae0c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 10V, Negative-QTOF	splash10-000i-0090000000-32e0ce93e0d175d484b3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 20V, Negative-QTOF	splash10-000i-0090000000-0ce743fedb4378c4da2b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 40V, Negative-QTOF	splash10-004i-0190000000-5eb996733ba6f3f7e74c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 10V, Positive-QTOF	splash10-000i-0090000000-8e23f9bfe8905382513a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 20V, Positive-QTOF	splash10-000i-0090000000-8e23f9bfe8905382513a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 40V, Positive-QTOF	splash10-004r-2090000000-a5032702bc127de0a3f6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 10V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 20V, Negative-QTOF	splash10-000i-0090000000-b07ca3aedb70714438e9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxy-hydromorphone 40V, Negative-QTOF	splash10-004r-0090000000-05533dbcd2b522bd02f0	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

35031791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769954

PDB ID

Not Available

ChEBI ID

174042

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

Not Available

Showing metabocard for 6alpha-Hydroxy-hydromorphone (HMDB0060796)

MOL for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

3D MOL for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

3D SDF for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

3D-SDF for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

PDB for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

3D PDB for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

SMILES for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

INCHI for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

Structure for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

3D Structure for HMDB0060796 (6alpha-Hydroxy-hydromorphone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra