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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:21:53 UTC

Update Date

2021-09-26 23:03:59 UTC

HMDB ID

HMDB0251769

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Embutramide

Description

Embutramide, also known as embutane, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Embutramide is an extremely weak basic (essentially neutral) compound (based on its pKa). Embutramide is formulated as a combination product under the brand name Tributame, which also contains chloroquine and lidocaine. Embutramide has however been reported to be used for suicide by people with access to the drug, and was added to the list of Schedule III drugs in the US in 2006, as a Non-Narcotic with ACSCN 2020, which classifies it with depressants such as benzodiazepines, barbiturates, and other sedative-hypnotics. Embutramide (INN, USAN, BAN) (brand name Embutane) is a potent opioid analgesic and sedative drug that is structurally related to methadone. Because of these properties, it was never adopted for medical use as an anesthetic as it was considered too dangerous for this purpose. It may cause significant pain to the animal being euthanized, and so may be less humane than older drugs used for this purpose such as pentobarbital; however, it may have less abuse potential than barbiturates especially in the Tributame combination formulation, and so is less likely to be diverted for recreational abuse. Instead it is used for euthanasia in veterinary medicine, mainly for the euthanization of dogs. Embutramide is used for euthanasia of a range of different animals, mainly small animals kept as pets rather than large farm animals. Along with strong sedative effects, embutramide also produces respiratory depression and ventricular arrhythmia. This compound has been identified in human blood as reported by (PMID: 31557052 ). Embutramide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Embutramide 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

HMDB0251769
     RDKit          3D
Embutramide
 48 48  0  0  0  0  0  0  0  0999 V2000
   -0.8813   -2.8657   -1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -2.7262   -0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6722   -1.3143    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476   -1.3683    1.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -1.8070    2.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473   -1.1352    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637    0.1152    0.7028 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662    0.2815    0.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937   -0.6572    0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3771    1.5358    1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8761    1.5983    0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752    1.4213   -0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7887    1.5056   -0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -0.3120   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299    0.1528   -1.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451    1.0751   -2.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8414    1.5970   -1.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    1.1695   -0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5356    1.6161   -0.0173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251    2.5382   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    0.2206    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -2.5420   -1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9157   -3.9785   -1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -2.3901   -2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -2.9449    0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -3.4537    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -0.3525    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467   -2.0236    2.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584   -2.6099    3.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191   -2.1561    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718   -0.9788    3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3451   -1.9381    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -1.3688   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664    0.8574    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380    2.3578    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917    1.6839    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4330    0.9728    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784    2.6577    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0437    0.4657   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925    2.2566   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1210    0.8570   -1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -0.1896   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    1.4376   -3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3901    2.3387   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5544    3.3848    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4484    2.0871   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0854    2.9834   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761   -0.0554    1.0848 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
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
M  END

1487
  Mrv0541 02231215312D          

 21 21  0  0  0  0            999 V2000
    1.6500   -3.2217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166   -1.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -0.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 21  1  0  0  0  0
  2 14  2  0  0  0  0
  3 20  1  0  0  0  0
  4  8  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  9 12  2  0  0  0  0
  9 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251769

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(CC)(CNC(=O)CCCO)C1=CC(OC)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO3/c1-4-17(5-2,13-18-16(20)10-7-11-19)14-8-6-9-15(12-14)21-3/h6,8-9,12,19H,4-5,7,10-11,13H2,1-3H3,(H,18,20)

> <INCHI_KEY>
LMBMDLOSPKIWAP-UHFFFAOYSA-N

> <FORMULA>
C17H27NO3

> <MOLECULAR_WEIGHT>
293.4012

> <EXACT_MASS>
293.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.93461266486641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-ethyl-2-(3-methoxyphenyl)butyl]-4-hydroxybutanamide

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.3893876959999996

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.25275050081188

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.626393017868423

> <JCHEM_PKA_STRONGEST_BASIC>
-0.06236279882040463

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
84.42170000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
embutramide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251769
     RDKit          3D
Embutramide
 48 48  0  0  0  0  0  0  0  0999 V2000
   -0.8813   -2.8657   -1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -2.7262   -0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6722   -1.3143    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476   -1.3683    1.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -1.8070    2.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473   -1.1352    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637    0.1152    0.7028 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662    0.2815    0.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937   -0.6572    0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3771    1.5358    1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8761    1.5983    0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752    1.4213   -0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7887    1.5056   -0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -0.3120   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299    0.1528   -1.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451    1.0751   -2.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8414    1.5970   -1.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    1.1695   -0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5356    1.6161   -0.0173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251    2.5382   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    0.2206    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -2.5420   -1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9157   -3.9785   -1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -2.3901   -2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -2.9449    0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -3.4537    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -0.3525    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467   -2.0236    2.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584   -2.6099    3.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191   -2.1561    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718   -0.9788    3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3451   -1.9381    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -1.3688   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664    0.8574    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380    2.3578    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917    1.6839    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4330    0.9728    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784    2.6577    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0437    0.4657   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925    2.2566   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1210    0.8570   -1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -0.1896   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    1.4376   -3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3901    2.3387   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5544    3.3848    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4484    2.0871   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0854    2.9834   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761   -0.0554    1.0848 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
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1487                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -6.014   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748   3.226   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748   7.077   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.081   0.916   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.748  -1.394   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.288  -1.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207  -1.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   0.146   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -2.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.058  -2.727   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.437  -0.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.704   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -3.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   2.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -5.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -5.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   3.226   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -6.014   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415   4.766   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748   5.536   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -7.554   0.000  0.00  0.00           C+0
CONECT    1   15   21                                                       
CONECT    2   14                                                            
CONECT    3   20                                                            
CONECT    4    8   14                                                       
CONECT    5    6    7    8    9                                             
CONECT    6    5   10                                                       
CONECT    7    5   11                                                       
CONECT    8    4    5                                                       
CONECT    9    5   12   13                                                  
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    9   15                                                       
CONECT   13    9   16                                                       
CONECT   14    2    4   17                                                  
CONECT   15    1   12   18                                                  
CONECT   16   13   18                                                       
CONECT   17   14   19                                                       
CONECT   18   15   16                                                       
CONECT   19   17   20                                                       
CONECT   20    3   19                                                       
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0251769
HETATM    1  C1  UNL     1      -0.881  -2.866  -1.560  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.004  -2.726  -0.081  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.672  -1.314   0.434  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.848  -1.368   1.924  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.146  -1.807   2.476  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.847  -1.135   0.277  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.364   0.115   0.703  1.00  0.00           N  
HETATM    8  C7  UNL     1       2.766   0.282   0.626  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.494  -0.657   0.202  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.377   1.536   1.037  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.876   1.598   0.883  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.375   1.421  -0.517  1.00  0.00           C  
HETATM   13  O2  UNL     1       6.789   1.506  -0.500  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.424  -0.312  -0.279  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.930   0.153  -1.518  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.645   1.075  -2.205  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.841   1.597  -1.764  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.348   1.169  -0.564  1.00  0.00           C  
HETATM   19  O3  UNL     1      -4.536   1.616  -0.017  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.425   2.538  -0.545  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.613   0.221   0.144  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.092  -2.542  -1.989  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.916  -3.979  -1.851  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.688  -2.390  -2.144  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.052  -2.945   0.185  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.280  -3.454   0.365  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.542  -0.352   2.357  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.047  -2.024   2.396  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.958  -2.610   3.289  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.919  -2.156   1.804  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.572  -0.979   3.111  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.345  -1.938   0.889  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.128  -1.369  -0.781  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.766   0.857   1.050  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.938   2.358   0.447  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.192   1.684   2.133  1.00  0.00           H  
HETATM   37  H16 UNL     1       5.433   0.973   1.623  1.00  0.00           H  
HETATM   38  H17 UNL     1       5.178   2.658   1.168  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.044   0.466  -0.934  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.993   2.257  -1.146  1.00  0.00           H  
HETATM   41  H20 UNL     1       7.121   0.857  -1.203  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.012  -0.190  -1.924  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.263   1.438  -3.170  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.390   2.339  -2.339  1.00  0.00           H  
HETATM   45  H24 UNL     1      -5.554   3.385   0.170  1.00  0.00           H  
HETATM   46  H25 UNL     1      -6.448   2.087  -0.697  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.085   2.983  -1.495  1.00  0.00           H  
HETATM   48  H27 UNL     1      -3.076  -0.055   1.085  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    6   14
CONECT    4    5   27   28
CONECT    5   29   30   31
CONECT    6    7   32   33
CONECT    7    8   34
CONECT    8    9    9   10
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   39   40
CONECT   13   41
CONECT   14   15   15   21
CONECT   15   16   42
CONECT   16   17   17   43
CONECT   17   18   44
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   45   46   47
CONECT   21   48
END

HMDB0251769
     RDKit          3D
Embutramide
 48 48  0  0  0  0  0  0  0  0999 V2000
   -0.8813   -2.8657   -1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -2.7262   -0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6722   -1.3143    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476   -1.3683    1.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462   -1.8070    2.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473   -1.1352    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637    0.1152    0.7028 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662    0.2815    0.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937   -0.6572    0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3771    1.5358    1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8761    1.5983    0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752    1.4213   -0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7887    1.5056   -0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -0.3120   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299    0.1528   -1.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451    1.0751   -2.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8414    1.5970   -1.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    1.1695   -0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5356    1.6161   -0.0173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251    2.5382   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    0.2206    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -2.5420   -1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9157   -3.9785   -1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -2.3901   -2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -2.9449    0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -3.4537    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -0.3525    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467   -2.0236    2.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584   -2.6099    3.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191   -2.1561    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718   -0.9788    3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3451   -1.9381    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -1.3688   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664    0.8574    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380    2.3578    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917    1.6839    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4330    0.9728    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784    2.6577    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0437    0.4657   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925    2.2566   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1210    0.8570   -1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -0.1896   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    1.4376   -3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3901    2.3387   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5544    3.3848    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4484    2.0871   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0854    2.9834   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761   -0.0554    1.0848 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
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Embutane	Kegg
N-(2-(3-Methoxyphenyl)-2-ethylbutyl-(1))-gamma-hydroxybutyramide	MeSH
N-[2-Ethyl-2-(3-methoxyphenyl)butyl]-4-hydroxybutanimidate	Generator

Chemical Formula

C₁₇H₂₇NO₃

Average Molecular Weight

293.4012

Monoisotopic Molecular Weight

293.199093735

IUPAC Name

N-[2-ethyl-2-(3-methoxyphenyl)butyl]-4-hydroxybutanamide

Traditional Name

embutramide

CAS Registry Number

Not Available

SMILES

CCC(CC)(CNC(=O)CCCO)C1=CC(OC)=CC=C1

InChI Identifier

InChI=1S/C17H27NO3/c1-4-17(5-2,13-18-16(20)10-7-11-19)14-8-6-9-15(12-14)21-3/h6,8-9,12,19H,4-5,7,10-11,13H2,1-3H3,(H,18,20)

InChI Key

LMBMDLOSPKIWAP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Alcohol
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
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)

Source

Exogenous

Exogenous (HMDB: HMDB0251769)

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	2.98	ALOGPS
logP	2.39	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	15.63	ChemAxon
pKa (Strongest Basic)	-0.062	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	84.42 m³·mol⁻¹	ChemAxon
Polarizability	33.93 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	173.183	30932474
DeepCCS	[M-H]-	170.825	30932474
DeepCCS	[M-2H]-	203.711	30932474
DeepCCS	[M+Na]+	179.276	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	170.9	32859911
AllCCS	[M+NH4]+	176.8	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	174.9	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Embutramide	CCC(CC)(CNC(=O)CCCO)C1=CC(OC)=CC=C1	3253.0	Standard polar	33892256
Embutramide	CCC(CC)(CNC(=O)CCCO)C1=CC(OC)=CC=C1	2323.1	Standard non polar	33892256
Embutramide	CCC(CC)(CNC(=O)CCCO)C1=CC(OC)=CC=C1	2426.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Embutramide,2TMS,isomer #1	CCC(CC)(CN(C(=O)CCCO[Si](C)(C)C)[Si](C)(C)C)C1=CC=CC(OC)=C1	2377.6	Semi standard non polar	33892256
Embutramide,2TMS,isomer #1	CCC(CC)(CN(C(=O)CCCO[Si](C)(C)C)[Si](C)(C)C)C1=CC=CC(OC)=C1	2467.2	Standard non polar	33892256
Embutramide,2TMS,isomer #1	CCC(CC)(CN(C(=O)CCCO[Si](C)(C)C)[Si](C)(C)C)C1=CC=CC(OC)=C1	2691.7	Standard polar	33892256
Embutramide,2TBDMS,isomer #1	CCC(CC)(CN(C(=O)CCCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC(OC)=C1	2843.6	Semi standard non polar	33892256
Embutramide,2TBDMS,isomer #1	CCC(CC)(CN(C(=O)CCCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC(OC)=C1	2856.2	Standard non polar	33892256
Embutramide,2TBDMS,isomer #1	CCC(CC)(CN(C(=O)CCCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC(OC)=C1	2876.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Embutramide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00p0-6950000000-8f9d785fdcc1e7f22071	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Embutramide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Embutramide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Embutramide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Embutramide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Embutramide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Embutramide 10V, Positive-QTOF	splash10-0a4l-0290000000-25155e75ff2a4455e43d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 20V, Positive-QTOF	splash10-0a4i-2790000000-ef0d7e7a7383c2d460c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 40V, Positive-QTOF	splash10-0006-2900000000-493d3e45e6a6ee055ea3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 10V, Negative-QTOF	splash10-0006-1190000000-224708ed861b68e814e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 20V, Negative-QTOF	splash10-0006-2290000000-37a640d74ea8e42b935e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 40V, Negative-QTOF	splash10-0006-9410000000-c9d5084b07ef00ed3303	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 10V, Positive-QTOF	splash10-0f96-7940000000-bcc334fd9d99b83ed07d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 20V, Positive-QTOF	splash10-0f6t-9700000000-e598c0334de261a2bd6a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 40V, Positive-QTOF	splash10-0zfs-9600000000-1b567777dc29537f61fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 10V, Negative-QTOF	splash10-054o-0390000000-f4699de747677412d3a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 20V, Negative-QTOF	splash10-056r-5950000000-2eae31c6718d01a36c5a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Embutramide 40V, Negative-QTOF	splash10-0006-9200000000-e05143c4437a1b43a05e	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

DB01487

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Embutramide

METLIN ID

Not Available

PubChem Compound

27453

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 Embutramide (HMDB0251769)

MOL for HMDB0251769 (Embutramide)

3D MOL for HMDB0251769 (Embutramide)

3D SDF for HMDB0251769 (Embutramide)

3D-SDF for HMDB0251769 (Embutramide)

PDB for HMDB0251769 (Embutramide)

3D PDB for HMDB0251769 (Embutramide)

SMILES for HMDB0251769 (Embutramide)

INCHI for HMDB0251769 (Embutramide)

Structure for HMDB0251769 (Embutramide)

3D Structure for HMDB0251769 (Embutramide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra