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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:33:29 UTC

Update Date

2021-09-14 15:19:57 UTC

HMDB ID

HMDB0060548

Secondary Accession Numbers

HMDB60548

Metabolite Identification

Common Name

Dihydromorphine

Description

Dihydromorphine, also known as paramorphan or 6α-hydromorphol, 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. Dihydromorphine is a very strong basic compound (based on its pKa). In humans, dihydromorphine is involved in dihydromorphine action pathway. Dihydromorphine acts as an agonist at the μ-opioid (mu), δ-opioid (delta) and κ-opioid (kappa) receptors. As with nicomorphine, MDMA, heroin (DEA 2013 production quota: 25 grammes) and the like, dihydromorphine is also used in research such as that mentioned above in properly licensed facilities; Form 225, the most common and least expensive individual researcher's license, does not include Schedule I so the lab must have a higher-level DEA registration As with other licit opioids used for medical purposes in other countries, including even much weaker opioids like nicocodeine, benzylmorphine, and tilidine, the reason for dihydromorphine being in Schedule I is that it was not in medical use in the US at time the Controlled Substances Act of 1970 was drawn up. Dihydromorphine's onset of action is more rapid than morphine and it also tends to have a longer duration of action, generally 4–7 hours. In comparison, the relative potency of dihydrocodeine is 1.15 times that of codeine. Dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and also is an active metabolite of the analgesic opioid drug dihydrocodeine. Dihydromorphine, often labelled with the isotope tritium in the form of [3H]-dihydromorphine, is used in scientific research to study binding of the opioid receptors in the nervous system. Under the Controlled Substances Act, dihydromorphine is listed as a Schedule I substance along with heroin.

Structure

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

HMDB0060548
     RDKit          3D
Dihydromorphine
 42 46  0  0  0  0  0  0  0  0999 V2000
    3.7528   -1.3416    0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -0.9694    0.0802 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    0.2455   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345    0.6349   -1.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    0.7434   -0.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7657   -0.1895   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768   -1.5065   -0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -2.3071   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999   -1.7295   -1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -0.3694   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034    0.2169   -2.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    0.4380   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816    1.7969   -1.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    2.0520   -0.4211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1584    2.3919    0.8586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3878    3.0036    0.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4995    1.1543    1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.3062    2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    0.3138    1.0098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3681   -1.0630    0.8445 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4905   -2.0956    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6614   -2.4075    1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138   -1.3162    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9628   -0.6946    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4650    0.0637   -1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    1.0797   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    1.6499   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.0838   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -3.3726   -0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6165   -2.3502   -1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825   -0.3262   -2.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    2.8690   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5504    3.1059    1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231    3.9875    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708    0.5908    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    1.4859    2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6889   -0.7166    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0603    0.7271    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879    0.9572    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -1.4175    1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434   -2.6940   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408   -2.8632    0.9684 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  6
  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  6
 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  1
 20 40  1  1
 21 41  1  0
 21 42  1  0
M  END


  Mrv1652305291919342D          

 24 28  0  0  0  0            999 V2000
10002.0474 9998.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9401 9998.0957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.823910001.0453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.823910001.6427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998910001.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.002010000.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.536610002.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.411910000.1040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.8239 9997.9853    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.824910000.2227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.412410000.9372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.587310000.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0609 9999.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.648410000.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6484 9998.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.176810000.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.351810000.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9393 9999.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3517 9998.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9723 9998.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.4124 9999.5082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.8233 9998.8005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.1767 9998.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5893 9999.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15  1  1  6  0  0  0
 11  8  1  6  0  0  0
 14 10  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19  2  1  0  0  0  0
 12 16  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 24 21  1  0  0  0  0
 22 15  1  0  0  0  0
 22  9  1  1  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 16  1  0  0  0  0
 23 20  1  0  0  0  0
 22 20  1  0  0  0  0
  6  5  1  0  0  0  0
 21  6  1  1  0  0  0
 10  3  1  1  0  0  0
 11  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060548

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O

> <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-KBQPJGBKSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.675439214909165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.0786493941262352

> <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>
10.288931769658

> <JCHEM_PKA_STRONGEST_BASIC>
9.235781522934591

> <JCHEM_POLAR_SURFACE_AREA>
52.93

> <JCHEM_REFRACTIVITY>
79.15980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060548
     RDKit          3D
Dihydromorphine
 42 46  0  0  0  0  0  0  0  0999 V2000
    3.7528   -1.3416    0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -0.9694    0.0802 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    0.2455   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345    0.6349   -1.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    0.7434   -0.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7657   -0.1895   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768   -1.5065   -0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -2.3071   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999   -1.7295   -1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -0.3694   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034    0.2169   -2.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    0.4380   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816    1.7969   -1.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    2.0520   -0.4211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1584    2.3919    0.8586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3878    3.0036    0.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4995    1.1543    1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.3062    2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    0.3138    1.0098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3681   -1.0630    0.8445 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4905   -2.0956    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6614   -2.4075    1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138   -1.3162    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9628   -0.6946    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4650    0.0637   -1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    1.0797   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    1.6499   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.0838   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -3.3726   -0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6165   -2.3502   -1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825   -0.3262   -2.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    2.8690   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5504    3.1059    1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231    3.9875    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708    0.5908    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    1.4859    2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6889   -0.7166    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0603    0.7271    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879    0.9572    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -1.4175    1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434   -2.6940   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408   -2.8632    0.9684 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  6
  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  6
 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  1
 20 40  1  1
 21 41  1  0
 21 42  1  0
M  END

HEADER    PROTEIN                                 29-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAY-19         0                                  
HETATM    1  O   UNK     0    8670.4888663.096   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8662.8228663.112   0.000  0.00  0.00           O+0
HETATM    3  H   UNK     0    8668.2058668.618   0.000  0.00  0.00           H+0
HETATM    4  N   UNK     0    8668.2058669.733   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8666.6658669.733   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8666.6708667.088   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8669.5358670.502   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0    8667.4368666.861   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8668.2058662.906   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8668.2068667.082   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.4368668.416   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.8968668.416   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.5148665.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.7448667.095   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.7448664.428   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.1308667.094   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.5908667.094   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.8208665.760   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.5908664.426   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8666.6158663.383   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8667.4368665.749   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.2038664.428   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8665.1308664.426   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8665.9008665.760   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   19                                                            
CONECT    3   10                                                            
CONECT    4    7   11    5                                                  
CONECT    5    6    4                                                       
CONECT    6    5   21                                                       
CONECT    7    4                                                            
CONECT    8   11                                                            
CONECT    9   22                                                            
CONECT   10   11   14   21    3                                             
CONECT   11   10   12    8    4                                             
CONECT   12   11   16                                                       
CONECT   13   14   15                                                       
CONECT   14   13   10                                                       
CONECT   15   13    1   22                                                  
CONECT   16   17   12   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2   23                                                  
CONECT   20   23   22                                                       
CONECT   21   10   22   24    6                                             
CONECT   22   21   15    9   20                                             
CONECT   23   19   24   20                                                  
CONECT   24   21   23   16                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0060548
HETATM    1  C1  UNL     1       3.753  -1.342   0.808  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.583  -0.969   0.080  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.723   0.245  -0.661  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.435   0.635  -1.313  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.290   0.743  -0.336  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.766  -0.189  -0.751  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.677  -1.507  -0.515  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.712  -2.307  -0.952  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.800  -1.729  -1.614  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.834  -0.369  -1.826  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.903   0.217  -2.480  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.793   0.438  -1.387  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.482   1.797  -1.410  1.00  0.00           O  
HETATM   14  C11 UNL     1      -0.438   2.052  -0.421  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.158   2.392   0.859  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.388   3.004   0.522  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.500   1.154   1.627  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.336   0.306   2.021  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.758   0.314   1.010  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.368  -1.063   0.844  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.491  -2.096   0.227  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.661  -2.408   1.130  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.614  -1.316   0.106  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.963  -0.695   1.684  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.465   0.064  -1.469  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.154   1.080  -0.051  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.589   1.650  -1.765  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.222  -0.084  -2.131  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.668  -3.373  -0.776  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.616  -2.350  -1.961  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.682  -0.326  -2.817  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.154   2.869  -0.835  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.550   3.106   1.451  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.323   3.987   0.607  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.271   0.591   1.024  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.098   1.486   2.530  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.689  -0.717   2.280  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.060   0.727   2.979  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.588   0.957   1.386  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.629  -1.417   1.878  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.043  -2.694  -0.552  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.141  -2.863   0.968  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

HMDB0060548
     RDKit          3D
Dihydromorphine
 42 46  0  0  0  0  0  0  0  0999 V2000
    3.7528   -1.3416    0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -0.9694    0.0802 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    0.2455   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345    0.6349   -1.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    0.7434   -0.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7657   -0.1895   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768   -1.5065   -0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -2.3071   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999   -1.7295   -1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -0.3694   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034    0.2169   -2.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    0.4380   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816    1.7969   -1.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    2.0520   -0.4211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1584    2.3919    0.8586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3878    3.0036    0.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4995    1.1543    1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.3062    2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    0.3138    1.0098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3681   -1.0630    0.8445 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4905   -2.0956    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6614   -2.4075    1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138   -1.3162    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9628   -0.6946    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4650    0.0637   -1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    1.0797   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    1.6499   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.0838   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -3.3726   -0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6165   -2.3502   -1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825   -0.3262   -2.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    2.8690   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5504    3.1059    1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231    3.9875    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708    0.5908    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    1.4859    2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6889   -0.7166    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0603    0.7271    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879    0.9572    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -1.4175    1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434   -2.6940   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408   -2.8632    0.9684 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  6
  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  6
 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  1
 20 40  1  1
 21 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Paramorphan	HMDB
Paramorfan	HMDB
(5alpha,6alpha)-4,5-Epoxy-17-methylmorphinan-3,6-diol	HMDB
(5Α,6α)-4,5-epoxy-17-methylmorphinan-3,6-diol	HMDB
6alpha-7,8-Dihydromorphine	HMDB
6alpha-Hydromorphol	HMDB
6Α-7,8-dihydromorphine	HMDB
6Α-hydromorphol	HMDB
7,8-Dihydromorphine	HMDB
DHM	HMDB
Hydromorphine	HMDB
alpha-Dihydromorphine	HMDB
Α-dihydromorphine	HMDB
Dihydromorphine	HMDB

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol

Traditional Name

(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol

CAS Registry Number

509-60-4

SMILES

[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O

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-KBQPJGBKSA-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

morphinane alkaloid (CHEBI:4575 )

Ontology

Disposition

Biological location

Cellular substructure

Cytoplasm

Non-excretory biofluid

Blood

Excreta

Urine

Organ

Kidney
Liver

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Dihydromorphine action pathway

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	163.6	30932474

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	30.68 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]+	164.799	31661259
DarkChem	[M-H]-	162.22	31661259
DeepCCS	[M-2H]-	209.043	30932474
DeepCCS	[M+Na]+	185.092	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydromorphine	[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O	3932.8	Standard polar	33892256
Dihydromorphine	[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O	2334.6	Standard non polar	33892256
Dihydromorphine	[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O	2475.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydromorphine,1TMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C5	2414.1	Semi standard non polar	33892256
Dihydromorphine,1TMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O)CC[C@H]3[C@H]1C5	2472.6	Semi standard non polar	33892256
Dihydromorphine,2TMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C5	2480.4	Semi standard non polar	33892256
Dihydromorphine,1TBDMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C5	2677.9	Semi standard non polar	33892256
Dihydromorphine,1TBDMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@@H](O)CC[C@H]3[C@H]1C5	2744.8	Semi standard non polar	33892256
Dihydromorphine,2TBDMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C5	2926.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydromorphine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2090000000-64b6783f4c86622fea8f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydromorphine GC-MS (2 TMS) - 70eV, Positive	splash10-01di-6309700000-61de6f13f6659db9e236	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydromorphine 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 - Dihydromorphine 10V, Positive-QTOF	splash10-000i-0090000000-504a9b2ff60a0d7f4411	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 20V, Positive-QTOF	splash10-000i-0090000000-c3e1bdcbec4cf28275c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 40V, Positive-QTOF	splash10-0kfx-4090000000-27a1656cb074b87c4b26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 10V, Negative-QTOF	splash10-000i-0090000000-6acbb360a4571844e9a1	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 20V, Negative-QTOF	splash10-000i-0090000000-6757484a2717da0640a0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 40V, Negative-QTOF	splash10-00bc-0290000000-a1dc3f7fe7b08229191d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 10V, Positive-QTOF	splash10-000i-0090000000-8e23f9bfe8905382513a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 20V, Positive-QTOF	splash10-000i-0090000000-1ec5d5a9442472265552	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 40V, Positive-QTOF	splash10-000i-0090000000-ab4dccbaff63f6897f59	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 10V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 20V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromorphine 40V, Negative-QTOF	splash10-000i-0090000000-842b3a0fd7fd18ba1b06	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Dihydromorphine 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	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

DB01565

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11782

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydromorphine

METLIN ID

Not Available

PubChem Compound

5359421

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

Not Available

Showing metabocard for Dihydromorphine (HMDB0060548)

MOL for HMDB0060548 (Dihydromorphine)

3D MOL for HMDB0060548 (Dihydromorphine)

3D SDF for HMDB0060548 (Dihydromorphine)

3D-SDF for HMDB0060548 (Dihydromorphine)

PDB for HMDB0060548 (Dihydromorphine)

3D PDB for HMDB0060548 (Dihydromorphine)

SMILES for HMDB0060548 (Dihydromorphine)

INCHI for HMDB0060548 (Dihydromorphine)

Structure for HMDB0060548 (Dihydromorphine)

3D Structure for HMDB0060548 (Dihydromorphine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra