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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:25:29 UTC

Update Date

2021-09-26 23:02:57 UTC

HMDB ID

HMDB0251120

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Diacetolol

Description

N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)ethanimidic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)ethanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Diacetolol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Diacetolol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0251120
     RDKit          3D
Diacetolol
 46 46  0  0  0  0  0  0  0  0999 V2000
    0.9485    2.4224   -2.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226    1.6789   -2.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942    2.0251   -3.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    0.5881   -1.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -0.0927   -1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556   -1.1360   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267   -1.7973   -0.6770 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -1.8015    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -1.1636    1.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9317   -2.4708    0.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922   -1.5072    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -0.8471   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    0.1832   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    0.8398   -1.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.7553   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.4937   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -0.6771   -2.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -0.2673   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0635   -0.0791    1.4116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2694    0.1515    2.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941   -1.0287    2.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    1.3718    1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    3.2454   -3.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    1.7679   -3.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    2.9157   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3733    0.1951   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468   -0.6302    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0721   -0.3959    1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3137   -1.8820    2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6940   -2.1756    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8240   -2.3192    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -1.1971    0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0834    1.0469    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409    1.5776   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -1.3865   -0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -1.5190   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8877   -1.1753   -0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7159    0.5688   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398   -0.9083    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9944    0.2659    3.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836   -1.9729    2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0727   -0.8578    2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5574   -1.1958    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045    2.1739    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7078    1.7469    2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5310    1.1206    0.6929 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  6 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
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 20 21  1  0
 20 22  1  0
 13  4  1  0
  1 23  1  0
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  1 25  1  0
  5 26  1  0
  9 27  1  0
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  9 29  1  0
 10 30  1  0
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 16 35  1  0
 17 36  1  0
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 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
M  END


  Mrv1652306031609512D          

 22 22  0  0  0  0            999 V2000
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  2  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  6  1  0  0  0  0
 16 15  2  0  0  0  0
 17  8  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  2  0  0  0  0
 18 13  1  4  0  0  0
 19 11  2  0  0  0  0
 20 12  1  0  0  0  0
 21 14  1  0  0  0  0
 22  9  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251120

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)COC1=C(C=C(C=C1)N=C(C)O)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O4/c1-10(2)17-8-14(21)9-22-16-6-5-13(18-12(4)20)7-15(16)11(3)19/h5-7,10,14,17,21H,8-9H2,1-4H3,(H,18,20)

> <INCHI_KEY>
AWOGXJOBNAWQSF-UHFFFAOYSA-N

> <FORMULA>
C16H24N2O4

> <MOLECULAR_WEIGHT>
308.378

> <EXACT_MASS>
308.173607261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.34877934110508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)ethanimidic acid

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
-1.3557292587754903

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.074081094420762

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.194431864642289

> <JCHEM_PKA_STRONGEST_BASIC>
9.566269400477958

> <JCHEM_POLAR_SURFACE_AREA>
91.15

> <JCHEM_REFRACTIVITY>
86.3964

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diacetolol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251120
     RDKit          3D
Diacetolol
 46 46  0  0  0  0  0  0  0  0999 V2000
    0.9485    2.4224   -2.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226    1.6789   -2.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942    2.0251   -3.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    0.5881   -1.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -0.0927   -1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556   -1.1360   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267   -1.7973   -0.6770 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -1.8015    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -1.1636    1.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9317   -2.4708    0.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922   -1.5072    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -0.8471   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    0.1832   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    0.8398   -1.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.7553   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.4937   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -0.6771   -2.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -0.2673   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0635   -0.0791    1.4116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2694    0.1515    2.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941   -1.0287    2.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    1.3718    1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    3.2454   -3.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    1.7679   -3.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    2.9157   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3733    0.1951   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468   -0.6302    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0721   -0.3959    1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3137   -1.8820    2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6940   -2.1756    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8240   -2.3192    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -1.1971    0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0834    1.0469    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409    1.5776   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -1.3865   -0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -1.5190   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8877   -1.1753   -0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7159    0.5688   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398   -0.9083    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9944    0.2659    3.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836   -1.9729    2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0727   -0.8578    2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5574   -1.1958    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045    2.1739    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7078    1.7469    2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5310    1.1206    0.6929 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  6 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 13  4  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6   13                                                       
CONECT    6    5   16                                                       
CONECT    7   13   15                                                       
CONECT    8   14   17                                                       
CONECT    9   14   22                                                       
CONECT   10    1    2   17                                                  
CONECT   11    3   15   19                                                  
CONECT   12    4   18   20                                                  
CONECT   13    5    7   18                                                  
CONECT   14    8    9   21                                                  
CONECT   15    7   11   16                                                  
CONECT   16    6   15   22                                                  
CONECT   17    8   10                                                       
CONECT   18   12   13                                                       
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22    9   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0251120
HETATM    1  C1  UNL     1       0.948   2.422  -2.891  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.223   1.679  -2.729  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.194   2.025  -3.456  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.347   0.588  -1.764  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.543  -0.093  -1.633  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.756  -1.136  -0.753  1.00  0.00           C  
HETATM    7  N1  UNL     1       5.027  -1.797  -0.677  1.00  0.00           N  
HETATM    8  C6  UNL     1       5.706  -1.802   0.403  1.00  0.00           C  
HETATM    9  C7  UNL     1       5.312  -1.164   1.673  1.00  0.00           C  
HETATM   10  O2  UNL     1       6.932  -2.471   0.381  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.692  -1.507   0.039  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.457  -0.847  -0.056  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.301   0.183  -0.949  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.127   0.840  -1.064  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.101   0.755  -0.485  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.891  -0.494  -0.650  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.091  -0.677  -2.035  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.249  -0.267  -0.000  1.00  0.00           C  
HETATM   19  N2  UNL     1      -3.064  -0.079   1.412  1.00  0.00           N  
HETATM   20  C14 UNL     1      -4.269   0.152   2.143  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.194  -1.029   2.054  1.00  0.00           C  
HETATM   22  C16 UNL     1      -4.965   1.372   1.605  1.00  0.00           C  
HETATM   23  H1  UNL     1       1.061   3.245  -3.655  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.104   1.768  -3.191  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.668   2.916  -1.947  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.373   0.195  -2.249  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.347  -0.630   1.624  1.00  0.00           H  
HETATM   28  H6  UNL     1       6.072  -0.396   1.930  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.314  -1.882   2.527  1.00  0.00           H  
HETATM   30  H8  UNL     1       7.694  -2.176   0.985  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.824  -2.319   0.738  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.669  -1.197   0.615  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.083   1.047   0.606  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.741   1.578  -0.941  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.485  -1.387  -0.201  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.662  -1.519  -2.298  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.888  -1.175  -0.137  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.716   0.569  -0.522  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.540  -0.908   1.767  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.994   0.266   3.217  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.684  -1.973   2.365  1.00  0.00           H  
HETATM   42  H20 UNL     1      -6.073  -0.858   2.732  1.00  0.00           H  
HETATM   43  H21 UNL     1      -5.557  -1.196   1.020  1.00  0.00           H  
HETATM   44  H22 UNL     1      -4.205   2.174   1.407  1.00  0.00           H  
HETATM   45  H23 UNL     1      -5.708   1.747   2.350  1.00  0.00           H  
HETATM   46  H24 UNL     1      -5.531   1.121   0.693  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5    5   13
CONECT    5    6   26
CONECT    6    7   11   11
CONECT    7    8    8
CONECT    8    9   10
CONECT    9   27   28   29
CONECT   10   30
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   14
CONECT   14   15
CONECT   15   16   33   34
CONECT   16   17   18   35
CONECT   17   36
CONECT   18   19   37   38
CONECT   19   20   39
CONECT   20   21   22   40
CONECT   21   41   42   43
CONECT   22   44   45   46
END

HMDB0251120
     RDKit          3D
Diacetolol
 46 46  0  0  0  0  0  0  0  0999 V2000
    0.9485    2.4224   -2.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226    1.6789   -2.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942    2.0251   -3.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    0.5881   -1.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -0.0927   -1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556   -1.1360   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267   -1.7973   -0.6770 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -1.8015    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -1.1636    1.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9317   -2.4708    0.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922   -1.5072    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -0.8471   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    0.1832   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    0.8398   -1.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.7553   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -0.4937   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -0.6771   -2.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493   -0.2673   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0635   -0.0791    1.4116 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2694    0.1515    2.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941   -1.0287    2.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    1.3718    1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    3.2454   -3.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    1.7679   -3.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    2.9157   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3733    0.1951   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468   -0.6302    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0721   -0.3959    1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3137   -1.8820    2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6940   -2.1756    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8240   -2.3192    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -1.1971    0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0834    1.0469    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409    1.5776   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -1.3865   -0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6618   -1.5190   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8877   -1.1753   -0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7159    0.5688   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398   -0.9083    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9944    0.2659    3.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836   -1.9729    2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0727   -0.8578    2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5574   -1.1958    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045    2.1739    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7078    1.7469    2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5310    1.1206    0.6929 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  6 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 13  4  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(3-Acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)ethanimidate	Generator
m And b 16,942	MeSH
Diacetolol, (+)-isomer	MeSH
Diacetolol, (+-)-isomer	MeSH
Diacetolol, monohydrochloride, (+-)-isomer	MeSH
Acetyl acebutolol	MeSH
Diacetolol monohydrochloride	MeSH
RS-1-(4-acetamido-2-Acetylphenoxy)-2-hydroxy-3-isopropylaminopropane hydrochloride	MeSH

Chemical Formula

C₁₆H₂₄N₂O₄

Average Molecular Weight

308.378

Monoisotopic Molecular Weight

308.173607261

IUPAC Name

N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)ethanimidic acid

Traditional Name

diacetolol

CAS Registry Number

Not Available

SMILES

CC(C)NCC(O)COC1=C(C=C(C=C1)N=C(C)O)C(C)=O

InChI Identifier

InChI=1S/C16H24N2O4/c1-10(2)17-8-14(21)9-22-16-6-5-13(18-12(4)20)7-15(16)11(3)19/h5-7,10,14,17,21H,8-9H2,1-4H3,(H,18,20)

InChI Key

AWOGXJOBNAWQSF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acetanilide
Acetophenone
N-acetylarylamine
Anilide
Phenoxy compound
Benzoyl
Aryl alkyl ketone
N-arylamide
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acetamide
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
1,2-aminoalcohol
Amino acid or derivatives
Secondary amine
Ether
Secondary aliphatic amine
Carboxylic acid derivative
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Organopnictogen compound
Alcohol
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

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
logP	0.8	ALOGPS
logP	-1.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	5.19	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	91.15 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	86.4 m³·mol⁻¹	ChemAxon
Polarizability	34.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	177.797	30932474
DeepCCS	[M-H]-	175.439	30932474
DeepCCS	[M-2H]-	208.325	30932474
DeepCCS	[M+Na]+	183.89	30932474
AllCCS	[M+H]+	175.3	32859911
AllCCS	[M+H-H2O]+	172.4	32859911
AllCCS	[M+NH4]+	178.0	32859911
AllCCS	[M+Na]+	178.8	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	177.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diacetolol	CC(C)NCC(O)COC1=C(C=C(C=C1)N=C(C)O)C(C)=O	3457.3	Standard polar	33892256
Diacetolol	CC(C)NCC(O)COC1=C(C=C(C=C1)N=C(C)O)C(C)=O	2646.0	Standard non polar	33892256
Diacetolol	CC(C)NCC(O)COC1=C(C=C(C=C1)N=C(C)O)C(C)=O	2506.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diacetolol,3TMS,isomer #1	CC(=O)C1=CC(N=C(C)O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2658.1	Semi standard non polar	33892256
Diacetolol,3TMS,isomer #1	CC(=O)C1=CC(N=C(C)O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2767.0	Standard non polar	33892256
Diacetolol,3TMS,isomer #1	CC(=O)C1=CC(N=C(C)O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	3046.4	Standard polar	33892256
Diacetolol,3TBDMS,isomer #1	CC(=O)C1=CC(N=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3368.6	Semi standard non polar	33892256
Diacetolol,3TBDMS,isomer #1	CC(=O)C1=CC(N=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3338.1	Standard non polar	33892256
Diacetolol,3TBDMS,isomer #1	CC(=O)C1=CC(N=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3266.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-8950000000-00d9e51430f9a7c2c3eb	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacetolol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 10V, Positive-QTOF	splash10-066r-1295000000-7d8fe76b7e2726ffe290	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 20V, Positive-QTOF	splash10-00xs-4290000000-ce4f2496c091e2201502	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 40V, Positive-QTOF	splash10-00di-9400000000-95ba3fe92fd79d75b092	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 10V, Negative-QTOF	splash10-0a4i-2649000000-be5df01545322d272d45	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 20V, Negative-QTOF	splash10-0006-1910000000-1feaf8911e2b355314ee	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 40V, Negative-QTOF	splash10-0002-1900000000-9bbd33f1beba8c15f1a2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 10V, Positive-QTOF	splash10-0a4i-0179000000-93b152f8b34e293323c1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 20V, Positive-QTOF	splash10-006t-9340000000-22b495cd4236bbc2c4dc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 40V, Positive-QTOF	splash10-0ab9-9400000000-8cdb85396ea81a88a724	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 10V, Negative-QTOF	splash10-0a4i-0894000000-2ebdadc86f74bee1c322	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 20V, Negative-QTOF	splash10-0006-5910000000-904579f27ec571908b66	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacetolol 40V, Negative-QTOF	splash10-0a5a-5900000000-dce12010cb78a4be733d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

46139

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Diacetolol (HMDB0251120)

MOL for HMDB0251120 (Diacetolol)

3D MOL for HMDB0251120 (Diacetolol)

3D SDF for HMDB0251120 (Diacetolol)

3D-SDF for HMDB0251120 (Diacetolol)

PDB for HMDB0251120 (Diacetolol)

3D PDB for HMDB0251120 (Diacetolol)

SMILES for HMDB0251120 (Diacetolol)

INCHI for HMDB0251120 (Diacetolol)

Structure for HMDB0251120 (Diacetolol)

3D Structure for HMDB0251120 (Diacetolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra