MiMeDB: Showing metabocard for Morphine (MMDBc0053452)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:25:00 UTC

Update Date

2024-09-29 15:37:09 UTC

Metabolite ID

MMDBc0053452

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>
MMDBc0053452

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₇H₁₉NO₃

Average Mass

285.3377

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Kidney
Liver

Tissue Locations

Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192111	UDP-glucuronosyltransferase 2B28	Enzyme	Q9BY64	Homo sapiens
MMDBp0192118	UDP-glucuronosyltransferase 2B4	Enzyme	P06133	Homo sapiens
MMDBp0192135	UDP-glucuronosyltransferase 1-4	Enzyme	P22310	Homo sapiens
MMDBp0192136	UDP-glucuronosyltransferase 2B10	Enzyme	P36537	Homo sapiens
MMDBp0192137	UDP-glucuronosyltransferase 2B7	Enzyme	P16662	Homo sapiens
MMDBp0192138	UDP-glucuronosyltransferase 2B15	Enzyme	P54855	Homo sapiens
MMDBp0192139	UDP-glucuronosyltransferase 2A1	Enzyme	Q9Y4X1	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192141	UDP-glucuronosyltransferase 1-9	Enzyme	O60656	Homo sapiens
MMDBp0192142	UDP-glucuronosyltransferase 1-8	Enzyme	Q9HAW9	Homo sapiens
MMDBp0192143	UDP-glucuronosyltransferase 1-3	Enzyme	P35503	Homo sapiens
MMDBp0192144	UDP-glucuronosyltransferase 1-10	Enzyme	Q9HAW8	Homo sapiens
MMDBp0192145	UDP-glucuronosyltransferase 2B17	Enzyme	O75795	Homo sapiens
MMDBp0192146	UDP-glucuronosyltransferase 1-6	Enzyme	P19224	Homo sapiens
MMDBp0192147	UDP-glucuronosyltransferase 1-5	Enzyme	P35504	Homo sapiens
MMDBp0192148	UDP-glucuronosyltransferase 2B11	Enzyme	O75310	Homo sapiens
MMDBp0192151	UDP-glucuronosyltransferase 1-7	Enzyme	Q9HAW7	Homo sapiens
MMDBp0192630	Cytochrome P450 3A4	Unknown	P08684	Homo sapiens
MMDBp0193103	Cytochrome P450 2D6	Unknown	P10635	Homo sapiens
MMDBp0193117	Cytochrome P450 2C8	Unknown	P10632	Homo sapiens
MMDBp0193419	Multidrug resistance protein 1	Transporter	P08183	Homo sapiens
MMDBp0193544	Delta-type opioid receptor	Unknown	P41143	Homo sapiens
MMDBp0193623	Mu-type opioid receptor	Unknown	P35372	Homo sapiens
MMDBp0194142	UDP-glucuronosyltransferase 2A3	Enzyme	Q6UWM9	Homo sapiens
MMDBp0194627	Kappa-type opioid receptor	Unknown	P41145	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human
Bacteria	nah	1	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Water	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0014440

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

References

Synthesis Reference

Not Available

General References

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 ]
Loguinov AV, Anderson LM, Crosby GJ, Yukhananov RY: Gene expression following acute morphine administration. Physiol Genomics. 2001 Aug 28;6(3):169-81. doi: 10.1152/physiolgenomics.2001.6.3.169. [PubMed:11526201 ]
Kilpatrick GJ, Smith TW: Morphine-6-glucuronide: actions and mechanisms. Med Res Rev. 2005 Sep;25(5):521-44. doi: 10.1002/med.20035. [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 ]
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 ]

Showing metabocard for Morphine (MMDBc0053452)

MOL for #<Metabolite:0x00007f922cd1e2f8>

3D MOL for #<Metabolite:0x00007f922cd1e2f8>

3D SDF for #<Metabolite:0x00007f922cd1e2f8>

3D-SDF for #<Metabolite:0x00007f922cd1e2f8>

PDB for #<Metabolite:0x00007f922cd1e2f8>

3D PDB for #<Metabolite:0x00007f922cd1e2f8>

SMILES for #<Metabolite:0x00007f922cd1e2f8>

INCHI for #<Metabolite:0x00007f922cd1e2f8>

Structure for #<Metabolite:0x00007f922cd1e2f8>

3D Structure for #<Metabolite:0x00007f922cd1e2f8>