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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24)transporters (1) Show 25 proteins XML

enzymes (24)transporters (1) Show 25 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2021-09-14 15:15:54 UTC

HMDB ID

HMDB0014440

Secondary Accession Numbers

HMDB14440

Metabolite Identification

Common Name

Morphine

Description

Morphine is the principal alkaloid in opium and the prototype opiate analgesic and narcotic. In 2017, morphine was the 155th most commonly prescribed medication in the United States, with more than four million prescriptions. Morphine is used primarily to treat both acute and chronic severe pain. Its duration of analgesia is about three to seven hours. A large overdose of morphine can cause asphyxia and death by respiratory depression if the person does not receive medical attention immediately. Morphine is naturally produced by several plants (such as the opium poppy) and animals (PMID: 22578954 ). Morphine was first isolated between 1803 and 1805 by Friedrich Sertürner. Sertürner originally named the substance morphium after the Greek god of dreams, Morpheus, as it has a tendency to cause sleep. The primary source of morphine is isolation from poppy straw of the opium poppy. Morphine is also endogenously produced by humans. In the mid 2000s it was found morphine can be synthesized by white blood cells (PMID 22578954 ). CYP2D6, a cytochrome P450 isoenzyme, catalyzes the biosynthesis of morphine from codeine and dopamine from tyramine. The morphine biosynthetic pathway in humans occurs as follows: L-tyrosine -> para-tyramine or L-DOPA -> dopamine -> (S)-norlaudanosoline -> (S)-reticuline -> 1,2-dehydroretinulinium -> (R)-reticuline -> salutaridine -> salutaridinol -> thebaine -> neopinone -> codeinone -> codeine -> morphine. (S)-Norlaudanosoline (also known as tetrahydropapaveroline) which is an important intermediate in the WBC biosynthesis of morphine can also be synthesized from 3,4-dihydroxyphenylacetaldehyde (DOPAL), a metabolite of L-DOPA and dopamine. Morphine has widespread effects in the central nervous system and on smooth muscle (PMID: 4582903 ). The precise mechanism of the analgesic action of morphine is not fully known. However, specific CNS opiate receptors have been identified and likely play a role in the induction of analgesic effects. Morphine first acts on the mu-opioid receptors. The mechanism of respiratory depression involves a reduction in the responsiveness of the brain stem respiratory centers to increases in carbon dioxide tension and electrical stimulation. It has been shown that morphine binds to and inhibits GABA inhibitory interneurons. These interneurons normally inhibit the descending pain inhibition pathway. So, without the inhibitory signals, pain modulation can proceed downstream. When the dose of morphine is reduced after long-term use, opioid withdrawal symptoms such as drowsiness, vomiting, and constipation may also occur (PMID: 23244430 ). Morphine is only found in easily detectable quantities in individuals that have used or taken this drug.

Structure

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

HMDB0014440
     RDKit          3D
Morphine
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.9368    0.1820    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694    0.6383    0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654   -0.1387    1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807   -0.1175    1.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676   -0.5385    0.5564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9264    0.5870    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4411    1.6710   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495    2.6404   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078    2.4847   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1440    1.3413    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4842    1.1635    0.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284    0.3672    0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -0.8612    1.0842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893   -1.6117    0.7216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3552   -2.4342   -0.4871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7288   -2.5203   -0.7205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -1.9539   -1.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519   -1.1692   -1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9584   -0.7276   -0.4945 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7687    0.5361   -0.6012 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9817    1.7808   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775   -0.8590    0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135    0.1499   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6926    0.8156    0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940    0.3095    2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -1.1927    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320    0.8818    2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -0.8280    2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645    3.5424   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184    3.2420   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694    0.3279    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448   -2.2048    1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -3.4834   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -2.5285    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -2.2753   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -0.8595   -2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785   -1.5246   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597    0.3995   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053    2.5764   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261    2.1912   -1.8802 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  1  0
 15 17  1  0
 17 18  2  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
 15 33  1  1
 16 34  1  0
 17 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

295
  Mrv0541 02231214352D          

 24 28  0  0  1  0            999 V2000
    1.9356    0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    2.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6296   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773    0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.6501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9151   -1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -1.3566    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.0645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.0180    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 16  1  0  0  0  0
 14  2  1  6  0  0  0
  3 20  1  0  0  0  0
  4  7  1  0  0  0  0
  4 12  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 15  1  0  0  0  0
  6 22  1  1  0  0  0
  7 11  1  0  0  0  0
  7 23  1  6  0  0  0
  8 14  1  0  0  0  0
  8 24  1  1  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 16  1  0  0  0  0
 11 13  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  2  0  0  0  0
 16 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014440

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

> <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/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1

> <INCHI_KEY>
BQJCRHHNABKAKU-KBQPJGBKSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.3377

> <EXACT_MASS>
285.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.951034386845045

> <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[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.8952108197005931

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.78310964250598

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.25560977784915

> <JCHEM_PKA_STRONGEST_BASIC>
9.1215849853492

> <JCHEM_POLAR_SURFACE_AREA>
52.93

> <JCHEM_REFRACTIVITY>
80.12240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
morph

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014440
     RDKit          3D
Morphine
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.9368    0.1820    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694    0.6383    0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654   -0.1387    1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807   -0.1175    1.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676   -0.5385    0.5564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9264    0.5870    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4411    1.6710   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495    2.6404   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078    2.4847   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1440    1.3413    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4842    1.1635    0.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284    0.3672    0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -0.8612    1.0842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893   -1.6117    0.7216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3552   -2.4342   -0.4871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7288   -2.5203   -0.7205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -1.9539   -1.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519   -1.1692   -1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9584   -0.7276   -0.4945 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7687    0.5361   -0.6012 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9817    1.7808   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775   -0.8590    0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135    0.1499   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6926    0.8156    0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940    0.3095    2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -1.1927    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320    0.8818    2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -0.8280    2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645    3.5424   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184    3.2420   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694    0.3279    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448   -2.2048    1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -3.4834   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -2.5285    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -2.2753   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -0.8595   -2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785   -1.5246   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597    0.3995   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053    2.5764   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261    2.1912   -1.8802 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  1  0
 15 17  1  0
 17 18  2  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
 15 33  1  1
 16 34  1  0
 17 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: 295                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.613   0.085   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.238  -3.890   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.238   3.890   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.975  -1.540   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.974  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.308  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.642  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.641  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.864   0.359   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.974   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.642   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.054   0.359   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.308   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.641  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.308  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.641   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.974  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.079  -2.726   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.308   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.641   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.974   3.850   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       8.141  -2.532   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       9.086  -1.987   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.397  -1.900   0.000  0.00  0.00           H+0
CONECT    1    8   16                                                       
CONECT    2   14                                                            
CONECT    3   20                                                            
CONECT    4    7   12   18                                                  
CONECT    5    6    8    9   10                                             
CONECT    6    5    7   15   22                                             
CONECT    7    4    6   11   23                                             
CONECT    8    1    5   14   24                                             
CONECT    9    5   12                                                       
CONECT   10    5   13   16                                                  
CONECT   11    7   13                                                       
CONECT   12    4    9                                                       
CONECT   13   10   11   19                                                  
CONECT   14    2    8   17                                                  
CONECT   15    6   17                                                       
CONECT   16    1   10   20                                                  
CONECT   17   14   15                                                       
CONECT   18    4                                                            
CONECT   19   13   21                                                       
CONECT   20    3   16   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    HMDB0014440
HETATM    1  C1  UNL     1       3.937   0.182   0.318  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.569   0.638   0.605  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.065  -0.139   1.694  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.581  -0.117   1.845  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.068  -0.539   0.556  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.926   0.587   0.099  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.441   1.671  -0.555  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.349   2.640  -0.918  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.708   2.485  -0.611  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.144   1.341   0.065  1.00  0.00           C  
HETATM   11  O1  UNL     1      -4.484   1.163   0.380  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.228   0.367   0.429  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.267  -0.861   1.084  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.089  -1.612   0.722  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.355  -2.434  -0.487  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.729  -2.520  -0.721  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.712  -1.954  -1.726  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.352  -1.169  -1.747  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.958  -0.728  -0.495  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.769   0.536  -0.601  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.982   1.781  -0.852  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.078  -0.859   0.702  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.113   0.150  -0.770  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.693   0.816   0.808  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.494   0.310   2.636  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.412  -1.193   1.703  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.232   0.882   2.189  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.309  -0.828   2.649  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.064   3.542  -1.441  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.418   3.242  -0.894  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.769   0.328   0.869  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.845  -2.205   1.630  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.006  -3.483  -0.267  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.223  -2.529   0.156  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.153  -2.275  -2.672  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.766  -0.859  -2.692  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.679  -1.525  -0.171  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.460   0.400  -1.469  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.405   2.576  -0.172  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.126   2.191  -1.880  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   18   35
CONECT   18   19   36
CONECT   19   20   37
CONECT   20   21   38
CONECT   21   39   40
END

HMDB0014440
     RDKit          3D
Morphine
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.9368    0.1820    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694    0.6383    0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654   -0.1387    1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807   -0.1175    1.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676   -0.5385    0.5564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9264    0.5870    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4411    1.6710   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495    2.6404   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078    2.4847   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1440    1.3413    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4842    1.1635    0.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284    0.3672    0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -0.8612    1.0842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893   -1.6117    0.7216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3552   -2.4342   -0.4871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7288   -2.5203   -0.7205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -1.9539   -1.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519   -1.1692   -1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9584   -0.7276   -0.4945 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7687    0.5361   -0.6012 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9817    1.7808   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775   -0.8590    0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135    0.1499   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6926    0.8156    0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940    0.3095    2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -1.1927    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320    0.8818    2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -0.8280    2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645    3.5424   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184    3.2420   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694    0.3279    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448   -2.2048    1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -3.4834   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -2.5285    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -2.2753   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -0.8595   -2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785   -1.5246   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597    0.3995   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053    2.5764   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261    2.1912   -1.8802 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  1  0
 15 17  1  0
 17 18  2  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
 15 33  1  1
 16 34  1  0
 17 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
(-)-Morphine	ChEBI
(5alpha,6alpha)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol	ChEBI
(5alpha,6alpha)-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol	ChEBI
(5R,6S,9R,13S,14R)-4,5-Epoxy-N-methyl-7-morphinen-3,6-diol	ChEBI
(7R,7AS,12BS)-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diol	ChEBI
Morfina	ChEBI
Morphia	ChEBI
Morphin	ChEBI
Morphinum	ChEBI
Morphium	ChEBI
Morfina dosa	Kegg
Substitol	Kegg
(5a,6a)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol	Generator
(5Α,6α)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol	Generator
(5a,6a)-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol	Generator
(5Α,6α)-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol	Generator
D-(-)-Morphine	HMDB
Morphina	HMDB
Morphine sulfate	HMDB
Contin, MS	HMDB
Morphine chloride	HMDB
Morphine sulfate (2:1), anhydrous	HMDB
Oramorph SR	HMDB
Sulfate, morphine	HMDB
Chloride, morphine	HMDB
MS Contin	HMDB
Duramorph	HMDB
Morphine sulfate (2:1), pentahydrate	HMDB

Chemical Formula

C₁₇H₁₉NO₃

Average Molecular Weight

285.3377

Monoisotopic Molecular Weight

285.136493479

IUPAC Name

(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol

Traditional Name

morph

CAS Registry Number

57-27-2

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

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/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1

InChI Key

BQJCRHHNABKAKU-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
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:17303 )
organic heteropentacyclic compound (CHEBI:17303 )
Alkaloids (C01516 )
Isoquinoline alkaloids (C01516 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Organ

Liver (HMDB: HMDB0014440)
Kidney (HMDB: HMDB0014440)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Route of exposure

Parenteral

Enteral

Ingestion (HMDB: HMDB0014440)
Rectal (HMDB: HMDB0014440)

Source

Exogenous

Exogenous (HMDB: HMDB0014440)

Environmental

Wastewater (HMDB: HMDB0014440)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0014440)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Heroin Action Pathway (HMDB: HMDB0014440)
Codeine Action Pathway (PathBank: SMP0000405)
Morphine Action Pathway (PathBank: SMP0000406)

Metabolic pathway

Codeine Metabolism Pathway (HMDB: HMDB0014440)
Codeine Metabolism Pathway (PathBank: SMP0000621)
Morphine Metabolism Pathway (PathBank: SMP0000622)
Heroin Metabolism Pathway (PathBank: SMP0000623)

Role

Industrial application

Mu-opioid receptor agonist (HMDB: HMDB0014440)
Opioid analgesic (HMDB: HMDB0014440)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0014440)

Biological role

Plant metabolite (HMDB: HMDB0014440)
Drug metabolite (HMDB: HMDB0014440)

Environmental role

Environmental contaminant (HMDB: HMDB0014440)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	255 °C (sulfate salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.2 g/L	Not Available
LogP	0.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	164.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.2 g/L	ALOGPS
logP	0.99	ALOGPS
logP	0.9	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.26	ChemAxon
pKa (Strongest Basic)	9.12	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	80.12 m³·mol⁻¹	ChemAxon
Polarizability	29.95 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]+	163.745	31661259
DarkChem	[M-H]-	160.738	31661259
DeepCCS	[M-2H]-	205.364	30932474
DeepCCS	[M+Na]+	181.083	30932474
AllCCS	[M+H]+	169.1	32859911
AllCCS	[M+H-H2O]+	165.7	32859911
AllCCS	[M+NH4]+	172.3	32859911
AllCCS	[M+Na]+	173.2	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	172.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Morphine	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O	3778.3	Standard polar	33892256
Morphine	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O	2315.9	Standard non polar	33892256
Morphine	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O	2456.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Morphine,1TMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5	2473.9	Semi standard non polar	33892256
Morphine,1TMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C)C=C[C@H]3[C@H]1C5	2450.8	Semi standard non polar	33892256
Morphine,2TMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O[Si](C)(C)C)C=C[C@H]3[C@H]1C5	2490.4	Semi standard non polar	33892256
Morphine,1TBDMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5	2744.1	Semi standard non polar	33892256
Morphine,1TBDMS,isomer #2	CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)C=C[C@H]3[C@H]1C5	2729.0	Semi standard non polar	33892256
Morphine,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)C=C[C@H]3[C@H]1C5	2974.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Morphine EI-B (Non-derivatized)	splash10-00li-8970000000-28acaf307ce4bc5aabf1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Morphine CI-B (Non-derivatized)	splash10-014i-0090000000-b9cf42b077ae0fa5b50d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Morphine EI-B (Non-derivatized)	splash10-00li-8970000000-28acaf307ce4bc5aabf1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Morphine CI-B (Non-derivatized)	splash10-014i-0090000000-b9cf42b077ae0fa5b50d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Morphine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vl-1090000000-adcd23ce75ad17f72cc5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Morphine GC-MS (2 TMS) - 70eV, Positive	splash10-03mi-7209800000-b1a234139ee9e72f3402	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Morphine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-QTOF , positive-QTOF	splash10-000i-0090000000-98125212ed8e73f219e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-QTOF , positive-QTOF	splash10-000i-0090000000-e9f7be236d827a716c1b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-QTOF , positive-QTOF	splash10-000i-0290000000-5066e10cd96a2c376676	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-QTOF , positive-QTOF	splash10-0kui-0930000000-793deeb91de6d2459cbe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-QTOF , positive-QTOF	splash10-100r-0900000000-f775c77035946f746daa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-0ufr-0390000000-660ff44516f98e346016	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-22857c8ef81e65ad6bd3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-c5194c99a9e7f30ea0c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-1980ff8ab9e654f16fe1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0690000000-efa51d970eaf96d3b982	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-0pc9-0920000000-64a693f2f51c03129c94	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-100r-0900000000-49174c3db4b1c1847080	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-3cc8784093ef460d3030	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-4bc885836f18b77696f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-4a16648c3e86669f2446	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-000i-0690000000-f41b2f804790e9ad8f1d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-0pc9-0920000000-69393fc6563baf39d91f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-100r-0900000000-467f39309be5edfa4c01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Morphine LC-ESI-ITFT , positive-QTOF	splash10-0ufr-0390000000-bd9670761ff2a7dafc55	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Morphine 10V, Positive-QTOF	splash10-000i-0090000000-46d12300d5a1a45af278	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Morphine 20V, Positive-QTOF	splash10-000i-0090000000-9470e4073083d671574a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Morphine 40V, Positive-QTOF	splash10-0pdj-3290000000-3c229ae6f1433ae20d85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Morphine 10V, Negative-QTOF	splash10-001i-0090000000-0d38f6180c7ffdd17c4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Morphine 20V, Negative-QTOF	splash10-001i-0090000000-e3fd836bcbf266246e22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Morphine 40V, Negative-QTOF	splash10-02di-0390000000-317675bcd07b96b05935	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Codeine Action Pathway		Not Available
Codeine Metabolism Pathway		Not Available
Morphine Action Pathway		Not Available
Morphine Metabolism Pathway		Not Available
Heroin 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 DB00295	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00295	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

DB00295

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Morphine

METLIN ID

Not Available

PubChem Compound

5288826

PDB ID

MOI

ChEBI ID

17303

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

Loguinov AV, Anderson LM, Crosby GJ, Yukhananov RY: Gene expression following acute morphine administration. Physiol Genomics. 2001 Aug 28;6(3):169-81. [PubMed:11526201 ]
Kilpatrick GJ, Smith TW: Morphine-6-glucuronide: actions and mechanisms. Med Res Rev. 2005 Sep;25(5):521-44. [PubMed:15952175 ]
Stefano GB, Ptacek R, Kuzelova H, Kream RM: Endogenous morphine: up-to-date review 2011. Folia Biol (Praha). 2012;58(2):49-56. [PubMed:22578954 ]
Jacquet YF, Lajtha A: Morphine action at central nervous system sites in rat: analgesia or hyperalgesia depending on site and dose. Science. 1973 Nov 2;182(4111):490-2. doi: 10.1126/science.182.4111.490. [PubMed:4582903 ]
Rehni AK, Jaggi AS, Singh N: Opioid withdrawal syndrome: emerging concepts and novel therapeutic targets. CNS Neurol Disord Drug Targets. 2013 Feb 1;12(1):112-25. doi: 10.2174/1871527311312010017. [PubMed:23244430 ]

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

References

Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [PubMed:20071451 ]

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

References

Coffman BL, Rios GR, King CD, Tephly TR: Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos. 1997 Jan;25(1):1-4. [PubMed:9010622 ]
Takeda S, Ishii Y, Iwanaga M, Mackenzie PI, Nagata K, Yamazoe Y, Oguri K, Yamada H: Modulation of UDP-glucuronosyltransferase function by cytochrome P450: evidence for the alteration of UGT2B7-catalyzed glucuronidation of morphine by CYP3A4. Mol Pharmacol. 2005 Mar;67(3):665-72. Epub 2004 Dec 20. [PubMed:15611481 ]
Yamada H, Ishii K, Ishii Y, Ieiri I, Nishio S, Morioka T, Oguri K: Formation of highly analgesic morphine-6-glucuronide following physiologic concentration of morphine in human brain. J Toxicol Sci. 2003 Dec;28(5):395-401. [PubMed:14746343 ]
Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [PubMed:20071451 ]

Enzyme Details

6. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

References

Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [PubMed:20071451 ]

Enzyme Details

7. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

References

Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. doi: 10.1124/dmd.107.019281. Epub 2008 Jan 10. [PubMed:18187562 ]

Enzyme Details

9. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-8

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A8
Uniprot ID:: Q9HAW9
Molecular weight:: 59741.035

Reactions

Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphate	details
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphate	details

References

Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. doi: 10.1124/dmd.107.019281. Epub 2008 Jan 10. [PubMed:18187562 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]

Only showing the first 10 proteins. There are 25 proteins in total.

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Showing metabocard for Morphine (HMDB0014440)

MOL for HMDB0014440 (Morphine)

3D MOL for HMDB0014440 (Morphine)

3D SDF for HMDB0014440 (Morphine)

3D-SDF for HMDB0014440 (Morphine)

PDB for HMDB0014440 (Morphine)

3D PDB for HMDB0014440 (Morphine)

SMILES for HMDB0014440 (Morphine)

INCHI for HMDB0014440 (Morphine)

Structure for HMDB0014440 (Morphine)

3D Structure for HMDB0014440 (Morphine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

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MS/MS Spectra

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