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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:40:28 UTC

Update Date

2021-09-14 15:45:57 UTC

HMDB ID

HMDB0041812

Secondary Accession Numbers

HMDB41812

Metabolite Identification

Common Name

6-Acetylmorphine

Description

6-Acetylmorphine, also known as 6-MAM or morphine 6-acetate, 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. 6-Acetylmorphine is a very strong basic compound (based on its pKa). Within humans, 6-acetylmorphine participates in a number of enzymatic reactions. In particular, 6-acetylmorphine and acetic acid can be biosynthesized from heroin; which is mediated by the enzymes liver carboxylesterase 1 and cocaine esterase. In addition, 6-acetylmorphine can be converted into morphine and acetic acid through its interaction with the enzymes liver carboxylesterase 1 and cocaine esterase. In humans, 6-acetylmorphine is involved in heroin metabolism pathway. 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.

Structure

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

HMDB0041812
     RDKit          3D
6-Acetylmorphine
 45 49  0  0  0  0  0  0  0  0999 V2000
    5.3330   -2.1368   -0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4419   -0.9561   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9313    0.1976   -0.5310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -1.0509   -0.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958    0.0584   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    0.2635   -1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -0.1363   -1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.8340   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031   -0.7706   -0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    0.5849   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959    1.5940   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179    2.9234   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1049    3.8128    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    3.3568    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    4.2224    1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872    2.0068    1.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5283    1.1882    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757   -0.2264    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -0.8926    1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.9062    1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -1.7290    0.0951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8686   -2.0114    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894   -0.0318    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4297    1.1900    1.4785 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3699   -1.7995   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -2.6972   -1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1982   -2.8264    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634    0.9397   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8979    0.7901   -2.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    0.0748   -2.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172   -1.9021   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -1.1439   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4879    0.5344   -0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127    0.9883   -1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    3.3095   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2993    4.8775    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8479    3.8690    2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -1.3758    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.1363    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -2.0083    2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791   -2.9148    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -2.4858    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543   -1.1972   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0553   -2.8012   -0.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568   -0.8114    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 23  5  1  0
 18  8  1  0
 21  9  1  0
 17 11  1  0
 24 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
M  END


  Mrv0541 09131211402D          

 24 28  0  0  0  0            999 V2000
    1.1769    4.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380   -1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3668    1.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    1.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764    1.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5753    1.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3228    0.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1796   -0.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2482    0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    3.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427    0.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    0.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1600    2.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315    2.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287    1.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171    2.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    2.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992   -0.4071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317    3.6647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4746    3.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792    3.2276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094    2.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 11  3  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16 11  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19  7  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 10  2  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
 24 17  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041812

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC23C4OC5=C(O)C=CC(CC1C2C=CC4OC(C)=O)=C35

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3

> <INCHI_KEY>
JJGYGPZNTOPXGV-UHFFFAOYSA-N

> <FORMULA>
C19H21NO4

> <MOLECULAR_WEIGHT>
327.3743

> <EXACT_MASS>
327.147058165

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.7110913824448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.3072111195070268

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.18771085943748

> <JCHEM_PKA_STRONGEST_BASIC>
9.084027049559483

> <JCHEM_POLAR_SURFACE_AREA>
59.000000000000014

> <JCHEM_REFRACTIVITY>
89.2739

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041812
     RDKit          3D
6-Acetylmorphine
 45 49  0  0  0  0  0  0  0  0999 V2000
    5.3330   -2.1368   -0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4419   -0.9561   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9313    0.1976   -0.5310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -1.0509   -0.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958    0.0584   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    0.2635   -1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -0.1363   -1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.8340   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031   -0.7706   -0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    0.5849   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959    1.5940   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179    2.9234   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1049    3.8128    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    3.3568    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    4.2224    1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872    2.0068    1.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5283    1.1882    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757   -0.2264    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -0.8926    1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.9062    1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -1.7290    0.0951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8686   -2.0114    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894   -0.0318    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4297    1.1900    1.4785 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3699   -1.7995   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -2.6972   -1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1982   -2.8264    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634    0.9397   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8979    0.7901   -2.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    0.0748   -2.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172   -1.9021   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -1.1439   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4879    0.5344   -0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127    0.9883   -1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    3.3095   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2993    4.8775    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8479    3.8690    2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -1.3758    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.1363    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -2.0083    2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791   -2.9148    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -2.4858    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543   -1.1972   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0553   -2.8012   -0.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568   -0.8114    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 23  5  1  0
 18  8  1  0
 21  9  1  0
 17 11  1  0
 24 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       2.197   8.619   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.804  -2.270   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.151   1.911   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.637   2.076   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.729   3.331   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.074   3.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.469   1.600   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.202  -0.049   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.063   0.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.668   7.162   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.618   1.749   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.440   1.798   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.550   0.331   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.765   4.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.112   4.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.654   2.949   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.192   4.368   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.638   4.263   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.023   2.703   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       3.545  -0.760   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       4.166   6.841   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.353   5.964   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.641   6.025   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.871   5.194   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   20                                                            
CONECT    3    5   11                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   15                                                       
CONECT    7    8   19                                                       
CONECT    8    7   20                                                       
CONECT    9   11   13                                                       
CONECT   10    1   21   23                                                  
CONECT   11    3    9   16                                                  
CONECT   12    4   13   19                                                  
CONECT   13    9   12   20                                                  
CONECT   14    5   17   22                                                  
CONECT   15    6   18   23                                                  
CONECT   16   11   17   19                                                  
CONECT   17   14   16   24                                                  
CONECT   18   15   19   24                                                  
CONECT   19    7   12   16   18                                             
CONECT   20    2    8   13                                                  
CONECT   21   10                                                            
CONECT   22   14                                                            
CONECT   23   10   15                                                       
CONECT   24   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0041812
HETATM    1  C1  UNL     1       5.333  -2.137  -0.860  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.442  -0.956  -0.684  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.931   0.198  -0.531  1.00  0.00           O  
HETATM    4  O2  UNL     1       3.067  -1.051  -0.679  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.196   0.058  -0.513  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.404   0.263  -1.728  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.154  -0.136  -1.886  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.488  -0.834  -0.771  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.003  -0.771  -0.834  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.591   0.585  -0.692  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.696   1.594  -0.089  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.018   2.923  -0.091  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.105   3.813   0.492  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.087   3.357   1.053  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.994   4.222   1.630  1.00  0.00           O  
HETATM   16  C13 UNL     1       0.387   2.007   1.041  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.528   1.188   0.466  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.076  -0.226   0.524  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.779  -0.893   1.653  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.789  -1.906   1.284  1.00  0.00           C  
HETATM   21  N1  UNL     1      -2.495  -1.729   0.095  1.00  0.00           N  
HETATM   22  C18 UNL     1      -3.869  -2.011   0.065  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.389  -0.032   0.742  1.00  0.00           C  
HETATM   24  O4  UNL     1       1.430   1.190   1.479  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.370  -1.800  -0.883  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.108  -2.697  -1.788  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.198  -2.826   0.000  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.863   0.940  -0.400  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.898   0.790  -2.567  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.334   0.075  -2.839  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.217  -1.902  -0.812  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.270  -1.144  -1.867  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.488   0.534  -0.005  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.013   0.988  -1.643  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.946   3.310  -0.524  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.299   4.878   0.524  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.848   3.869   2.029  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.002  -1.376   2.298  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.264  -0.136   2.338  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.525  -2.008   2.136  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.279  -2.915   1.260  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.176  -2.486   1.019  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.554  -1.197  -0.157  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.055  -2.801  -0.721  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.757  -0.811   1.435  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   23   28
CONECT    6    7    7   29
CONECT    7    8   30
CONECT    8    9   18   31
CONECT    9   10   21   32
CONECT   10   11   33   34
CONECT   11   12   12   17
CONECT   12   13   35
CONECT   13   14   14   36
CONECT   14   15   16
CONECT   15   37
CONECT   16   17   17   24
CONECT   17   18
CONECT   18   19   23
CONECT   19   20   38   39
CONECT   20   21   40   41
CONECT   21   22
CONECT   22   42   43   44
CONECT   23   24   45
END

HMDB0041812
     RDKit          3D
6-Acetylmorphine
 45 49  0  0  0  0  0  0  0  0999 V2000
    5.3330   -2.1368   -0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4419   -0.9561   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9313    0.1976   -0.5310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -1.0509   -0.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958    0.0584   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    0.2635   -1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -0.1363   -1.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.8340   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031   -0.7706   -0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    0.5849   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959    1.5940   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179    2.9234   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1049    3.8128    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    3.3568    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    4.2224    1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872    2.0068    1.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5283    1.1882    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757   -0.2264    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -0.8926    1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.9062    1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -1.7290    0.0951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8686   -2.0114    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894   -0.0318    0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4297    1.1900    1.4785 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3699   -1.7995   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -2.6972   -1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1982   -2.8264    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634    0.9397   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8979    0.7901   -2.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    0.0748   -2.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172   -1.9021   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -1.1439   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4879    0.5344   -0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127    0.9883   -1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    3.3095   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2993    4.8775    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8479    3.8690    2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -1.3758    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.1363    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -2.0083    2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791   -2.9148    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -2.4858    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543   -1.1972   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0553   -2.8012   -0.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568   -0.8114    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 23  5  1  0
 18  8  1  0
 21  9  1  0
 17 11  1  0
 24 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-MAM	HMDB
6-Monoacetylmorphine	HMDB
6-O-Acetylmorphine	HMDB
6-O-Monoacetylmorphine	HMDB
a-Monoacetyl-morphine	HMDB
Monoacetylmorphine	HMDB
Morphine 6-acetate	HMDB
O6 Monoacetylmorphine	HMDB
6-MAM CPD	HMDB
Morphine-6-acetate	HMDB
6-(0-Acetyl)morphine	HMDB
6-O-Monoacetylmorphine hydrochloride, (5alpha,6alpha)-isomer	HMDB

Chemical Formula

C₁₉H₂₁NO₄

Average Molecular Weight

327.3743

Monoisotopic Molecular Weight

327.147058165

IUPAC Name

10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate

Traditional Name

10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate

CAS Registry Number

2784-73-8

SMILES

CN1CCC23C4OC5=C(O)C=CC(CC1C2C=CC4OC(C)=O)=C35

InChI Identifier

InChI=1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3

InChI Key

JJGYGPZNTOPXGV-UHFFFAOYSA-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
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	1.9	ALOGPS
logP	1.31	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.27 m³·mol⁻¹	ChemAxon
Polarizability	34.71 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]+	176.454	31661259
DarkChem	[M-H]-	172.246	31661259
DeepCCS	[M-2H]-	206.38	30932474
DeepCCS	[M+Na]+	181.607	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	181.4	32859911
AllCCS	[M+Na]+	182.2	32859911
AllCCS	[M-H]-	183.1	32859911
AllCCS	[M+Na-2H]-	182.6	32859911
AllCCS	[M+HCOO]-	182.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Acetylmorphine	CN1CCC23C4OC5=C(O)C=CC(CC1C2C=CC4OC(C)=O)=C35	3866.9	Standard polar	33892256
6-Acetylmorphine	CN1CCC23C4OC5=C(O)C=CC(CC1C2C=CC4OC(C)=O)=C35	2547.5	Standard non polar	33892256
6-Acetylmorphine	CN1CCC23C4OC5=C(O)C=CC(CC1C2C=CC4OC(C)=O)=C35	2600.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Acetylmorphine,1TMS,isomer #1	CC(=O)OC1C=CC2C3CC4=CC=C(O[Si](C)(C)C)C5=C4C2(CCN3C)C1O5	2595.4	Semi standard non polar	33892256
6-Acetylmorphine,1TBDMS,isomer #1	CC(=O)OC1C=CC2C3CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4C2(CCN3C)C1O5	2840.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Acetylmorphine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8092000000-9d66631288fe4f66c790	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Acetylmorphine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-8009000000-52b47a4992bdbd81c484	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Acetylmorphine 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 - 6-Acetylmorphine LC-ESI-QTOF , positive-QTOF	splash10-004i-0129000000-5471df3df6acdae4d4b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Acetylmorphine -1V, Positive-QTOF	splash10-004i-0129000000-5842d0f2507c059681e6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 10V, Negative-QTOF	splash10-0059-3059000000-c3b4e5af4d0f8422135c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 20V, Negative-QTOF	splash10-003r-4093000000-4656131edcd16df76332	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 40V, Negative-QTOF	splash10-0a4l-8090000000-a6a34ebc747c34b19fd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 10V, Negative-QTOF	splash10-004i-2079000000-23e754d670ade7a54f3c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 20V, Negative-QTOF	splash10-0a4i-9021000000-0950ccebf50cfaad3a1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 40V, Negative-QTOF	splash10-0adi-7079000000-4fb47d8b0e5e8226521a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 10V, Positive-QTOF	splash10-004i-1098000000-93911ba27c15dd97e3e2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 20V, Positive-QTOF	splash10-00n0-1092000000-ddc7bfbf778152ac0e23	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 40V, Positive-QTOF	splash10-0aym-3090000000-cf6e08778a9a8ff75a32	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 10V, Positive-QTOF	splash10-004i-0019000000-521926133e29807da794	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 20V, Positive-QTOF	splash10-004i-0029000000-2962ac8b01632069e30b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetylmorphine 40V, Positive-QTOF	splash10-00or-0093000000-d9e55425ae545b6b80f1	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Heroin Action Pathway		Not Available
Heroin Metabolism Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

453890

KEGG Compound ID

C11781

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetylmorphine

METLIN ID

Not Available

PubChem Compound

520352

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 6-Acetylmorphine (HMDB0041812)

MOL for HMDB0041812 (6-Acetylmorphine)

3D MOL for HMDB0041812 (6-Acetylmorphine)

3D SDF for HMDB0041812 (6-Acetylmorphine)

3D-SDF for HMDB0041812 (6-Acetylmorphine)

PDB for HMDB0041812 (6-Acetylmorphine)

3D PDB for HMDB0041812 (6-Acetylmorphine)

SMILES for HMDB0041812 (6-Acetylmorphine)

INCHI for HMDB0041812 (6-Acetylmorphine)

Structure for HMDB0041812 (6-Acetylmorphine)

3D Structure for HMDB0041812 (6-Acetylmorphine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra