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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014472

Secondary Accession Numbers

HMDB14472

Metabolite Identification

Common Name

Hydromorphone

Description

Hydromorphone is only found in individuals that have used or taken this drug. It is an opioid analgesic derived from morphine and used mainly as an analgesic. It has a shorter duration of action and is more potent than morphine. [PubChem]Hydromorphone is a narcotic analgesic; its principal therapeutic effect is relief of pain. Hydromorphone interacts predominantly with the opioid mu-receptors. These mu-binding sites are discretely distributed in the human brain, with high densities in the posterior amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and certain cortical areas. They are also found on the terminal axons of primary afferents within laminae I and II (substantia gelatinosa) of the spinal cord and in the spinal nucleus of the trigeminal nerve. In clinical settings, Hydromorphone exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Hydromorphone also binds with kappa-receptors which are thought to mediate spinal analgesia, miosis and sedation.

Structure

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

HMDB0014472
     RDKit          3D
Hydromorphone
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.8246    0.5333    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476    0.8189    0.2770 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    0.6535    1.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372    0.2067    1.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768   -0.4794    0.7632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0595    0.4466    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    1.3516   -0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    2.1702   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798    2.0470   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2956    1.0871    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5842    0.9509    0.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173    0.2575    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -0.7775    1.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0158   -1.5357    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3199   -2.5683    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -3.6353    0.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -2.2743   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -1.7403   -1.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994   -0.9263   -0.2670 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5821    0.3323   -0.7484 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094    1.4184   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1161   -0.5040    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0242    0.8208   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4332    1.2566    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1631    1.6464    2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -0.0288    2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131    1.0623    2.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -0.4944    2.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    2.9162   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7672    2.6865   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8155    0.2674    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659   -1.9848    2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2164   -3.1903   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -1.4739   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.1308   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072   -2.6121   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -1.5095    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2435    0.0086   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.5267   -2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1020    2.4002   -0.8624 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
  5  4  1  1
  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  2  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  1
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  1
 20 38  1  6
 21 39  1  0
 21 40  1  0
M  END

327
  Mrv0541 02231214362D          

 24 28  0  0  1  0            999 V2000
    1.9356   -0.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    1.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -1.0939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.6814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -1.0939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6296   -0.6814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -1.0939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773   -0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -1.6255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.3334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.2870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 17  1  0  0  0  0
  2 16  2  0  0  0  0
  3 20  1  0  0  0  0
  4  7  1  0  0  0  0
  4 13  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  1  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 22  1  1  0  0  0
  7 12  1  0  0  0  0
  7 23  1  6  0  0  0
  8 16  1  0  0  0  0
  8 24  1  1  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 10 17  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014472

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/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/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1

> <INCHI_KEY>
WVLOADHCBXTIJK-YNHQPCIGSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.3377

> <EXACT_MASS>
285.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.023248428425724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.6227496759764108

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.00207891919619

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.107628114711872

> <JCHEM_PKA_STRONGEST_BASIC>
8.586674910405563

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
78.26240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydromorphone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014472
     RDKit          3D
Hydromorphone
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.8246    0.5333    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476    0.8189    0.2770 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    0.6535    1.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372    0.2067    1.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768   -0.4794    0.7632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0595    0.4466    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    1.3516   -0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    2.1702   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798    2.0470   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2956    1.0871    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5842    0.9509    0.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173    0.2575    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -0.7775    1.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0158   -1.5357    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3199   -2.5683    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -3.6353    0.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -2.2743   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -1.7403   -1.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994   -0.9263   -0.2670 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5821    0.3323   -0.7484 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094    1.4184   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1161   -0.5040    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0242    0.8208   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4332    1.2566    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1631    1.6464    2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -0.0288    2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131    1.0623    2.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -0.4944    2.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    2.9162   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7672    2.6865   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8155    0.2674    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659   -1.9848    2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2164   -3.1903   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -1.4739   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.1308   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072   -2.6121   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -1.5095    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2435    0.0086   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.5267   -2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1020    2.4002   -0.8624 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
  5  4  1  1
  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  2  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  1
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  1
 20 38  1  6
 21 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 327                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.613  -0.416   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.238  -4.392   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.238   3.388   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.975  -2.042   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.974  -1.272   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.308  -2.042   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.642  -1.272   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.641  -2.042   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.864  -0.143   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.974   0.268   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.308  -3.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.642   0.268   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.054  -0.143   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.308   1.038   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.974  -4.352   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.641  -3.582   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.641   1.038   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.079  -3.227   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.308   2.578   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.641   2.578   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.974   3.348   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       8.141  -3.034   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       9.086  -2.489   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.397  -2.402   0.000  0.00  0.00           H+0
CONECT    1    8   17                                                       
CONECT    2   16                                                            
CONECT    3   20                                                            
CONECT    4    7   13   18                                                  
CONECT    5    6    8    9   10                                             
CONECT    6    5    7   11   22                                             
CONECT    7    4    6   12   23                                             
CONECT    8    1    5   16   24                                             
CONECT    9    5   13                                                       
CONECT   10    5   14   17                                                  
CONECT   11    6   15                                                       
CONECT   12    7   14                                                       
CONECT   13    4    9                                                       
CONECT   14   10   12   19                                                  
CONECT   15   11   16                                                       
CONECT   16    2    8   15                                                  
CONECT   17    1   10   20                                                  
CONECT   18    4                                                            
CONECT   19   14   21                                                       
CONECT   20    3   17   21                                                  
CONECT   21   19   20                                                       
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0014472
HETATM    1  C1  UNL     1       3.825   0.533   0.024  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.448   0.819   0.277  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.016   0.654   1.612  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.637   0.207   1.862  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.077  -0.479   0.763  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.060   0.447   0.154  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.698   1.352  -0.780  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.679   2.170  -1.275  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.980   2.047  -0.814  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.296   1.087   0.156  1.00  0.00           C  
HETATM   11  O1  UNL     1      -4.584   0.951   0.625  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.317   0.257   0.662  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.215  -0.778   1.587  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.016  -1.536   1.290  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.320  -2.568   0.286  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.795  -3.635   0.631  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.035  -2.274  -1.132  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.350  -1.740  -1.367  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.899  -0.926  -0.267  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.582   0.332  -0.748  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.709   1.418  -1.244  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.116  -0.504   0.187  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.024   0.821  -1.049  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.433   1.257   0.637  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.163   1.646   2.135  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.740  -0.029   2.128  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.013   1.062   2.214  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.616  -0.494   2.752  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.415   2.916  -2.035  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.767   2.687  -1.195  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.815   0.267   1.318  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.666  -1.985   2.228  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.216  -3.190  -1.732  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.745  -1.474  -1.473  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.378  -1.131  -2.307  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.007  -2.612  -1.565  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.703  -1.509   0.274  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.244   0.009  -1.606  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.717   1.527  -2.351  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.102   2.400  -0.862  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   16   17
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   20   37
CONECT   20   21   38
CONECT   21   39   40
END

HMDB0014472
     RDKit          3D
Hydromorphone
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.8246    0.5333    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4476    0.8189    0.2770 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    0.6535    1.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372    0.2067    1.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768   -0.4794    0.7632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0595    0.4466    0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    1.3516   -0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    2.1702   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798    2.0470   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2956    1.0871    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5842    0.9509    0.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173    0.2575    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -0.7775    1.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0158   -1.5357    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3199   -2.5683    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -3.6353    0.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -2.2743   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -1.7403   -1.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994   -0.9263   -0.2670 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5821    0.3323   -0.7484 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7094    1.4184   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1161   -0.5040    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0242    0.8208   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4332    1.2566    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1631    1.6464    2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -0.0288    2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131    1.0623    2.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -0.4944    2.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    2.9162   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7672    2.6865   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8155    0.2674    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659   -1.9848    2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2164   -3.1903   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -1.4739   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.1308   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072   -2.6121   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -1.5095    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2435    0.0086   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.5267   -2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1020    2.4002   -0.8624 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
  5  4  1  1
  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  2  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  1
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  1
 20 38  1  6
 21 39  1  0
 21 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-(5R)-4,5-Epoxy-3-hydroxy-9alpha-methylmorphinan-6-one	ChEBI
4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-one	ChEBI
4,5alpha-Epoxy-3-hydroxy-17-methyl-6-morphinanone	ChEBI
6-Deoxy-7,8-dihydro-6-oxomorphine	ChEBI
7,8-Dihydromorphinone	ChEBI
Dihydromorfinon	ChEBI
Dihydromorphinone	ChEBI
Dimorphone	ChEBI
Hidromorfona	ChEBI
Hydromorfona	ChEBI
Hydromorphonum	ChEBI
Idromorfone	ChEBI
(-)-(5R)-4,5-Epoxy-3-hydroxy-9a-methylmorphinan-6-one	Generator
(-)-(5R)-4,5-Epoxy-3-hydroxy-9α-methylmorphinan-6-one	Generator
4,5a-Epoxy-3-hydroxy-17-methyl-6-morphinanone	Generator
4,5Α-epoxy-3-hydroxy-17-methyl-6-morphinanone	Generator
Hydromorphon	HMDB
Hydromorphone hydrochloride	HMDB
Laudacon	HMDB
Dilaudid	HMDB
Palladone	HMDB

Chemical Formula

C₁₇H₁₉NO₃

Average Molecular Weight

285.3377

Monoisotopic Molecular Weight

285.136493479

IUPAC Name

(1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one

Traditional Name

hydromorphone

CAS Registry Number

466-99-9

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O

InChI Identifier

InChI=1S/C17H19NO3/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/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1

InChI Key

WVLOADHCBXTIJK-YNHQPCIGSA-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
Isoquinolone
Tetralin
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Ether
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:5790 )
organic heteropentacyclic compound (CHEBI:5790 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	266 - 267 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.39 g/L	Not Available
LogP	0.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	163.9	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.39 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.62	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	8.59	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.26 m³·mol⁻¹	ChemAxon
Polarizability	30.02 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]+	167.078	31661259
DarkChem	[M-H]-	160.353	31661259
DeepCCS	[M-2H]-	207.01	30932474
DeepCCS	[M+Na]+	183.136	30932474
AllCCS	[M+H]+	168.2	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.3	32859911
AllCCS	[M+Na]+	172.2	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	173.4	32859911
AllCCS	[M+HCOO]-	172.8	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.	3.4 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8883 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	108.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1093.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	302.9 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	322.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	555.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	736.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	263.8 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	925.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	440.2 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	102.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydromorphone	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O	3929.3	Standard polar	33892256
Hydromorphone	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O	2350.7	Standard non polar	33892256
Hydromorphone	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O	2507.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydromorphone,1TMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(=O)CC[C@H]3[C@H]1C5	2546.6	Semi standard non polar	33892256
Hydromorphone,1TMS,isomer #2	CN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O)C(=C13)O4	2493.7	Semi standard non polar	33892256
Hydromorphone,1TMS,isomer #3	CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@H]3[C@H]1C5	2464.4	Semi standard non polar	33892256
Hydromorphone,2TMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O4	2520.4	Semi standard non polar	33892256
Hydromorphone,2TMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O4	2529.9	Standard non polar	33892256
Hydromorphone,2TMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O4	3031.1	Standard polar	33892256
Hydromorphone,2TMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@H]3[C@H]1C5	2508.7	Semi standard non polar	33892256
Hydromorphone,2TMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@H]3[C@H]1C5	2484.8	Standard non polar	33892256
Hydromorphone,2TMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@H]3[C@H]1C5	3009.9	Standard polar	33892256
Hydromorphone,1TBDMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(=O)CC[C@H]3[C@H]1C5	2811.4	Semi standard non polar	33892256
Hydromorphone,1TBDMS,isomer #2	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O)C(=C13)O4	2745.4	Semi standard non polar	33892256
Hydromorphone,1TBDMS,isomer #3	CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@H]3[C@H]1C5	2721.8	Semi standard non polar	33892256
Hydromorphone,2TBDMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O4	2988.7	Semi standard non polar	33892256
Hydromorphone,2TBDMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O4	2994.3	Standard non polar	33892256
Hydromorphone,2TBDMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O4	3270.4	Standard polar	33892256
Hydromorphone,2TBDMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@H]3[C@H]1C5	2973.5	Semi standard non polar	33892256
Hydromorphone,2TBDMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@H]3[C@H]1C5	2889.3	Standard non polar	33892256
Hydromorphone,2TBDMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@H]3[C@H]1C5	3241.3	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Hydromorphone Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00327	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00327	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00327

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447624

KEGG Compound ID

C07042

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydromorphinone

METLIN ID

Not Available

PubChem Compound

5284570

PDB ID

Not Available

ChEBI ID

5790

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

Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL: Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects. J Clin Pharmacol. 1981 Apr;21(4):152-6. [PubMed:6165742 ]
Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. [PubMed:12818953 ]

Showing metabocard for Hydromorphone (HMDB0014472)

MOL for HMDB0014472 (Hydromorphone)

3D MOL for HMDB0014472 (Hydromorphone)

3D SDF for HMDB0014472 (Hydromorphone)

3D-SDF for HMDB0014472 (Hydromorphone)

PDB for HMDB0014472 (Hydromorphone)

3D PDB for HMDB0014472 (Hydromorphone)

SMILES for HMDB0014472 (Hydromorphone)

INCHI for HMDB0014472 (Hydromorphone)

Structure for HMDB0014472 (Hydromorphone)

3D Structure for HMDB0014472 (Hydromorphone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized