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Showing metabocard for Dimethylethanolamine (HMDB0032231)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:48:37 UTC
Update Date2023-02-21 17:21:46 UTC
HMDB IDHMDB0032231
Secondary Accession Numbers
  • HMDB32231
Metabolite Identification
Common NameDimethylethanolamine
DescriptionDimethylethanolamine, also known as 2-dimethylaminoethanol or DMEA, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Dimethylethanolamine is naturally produced in the human body and can also be found in fatty fish. It is also used as a food additive ("EAFUS: Everything Added to Food in the United States. "). Dimethylethanolamine is a potentially toxic compound. Dimethylethanolamine has been used in the treatment of attention deficit-hyperactivity disorder (ADHD), Alzheimer's disease, autism, and tardive dyskinesia. Dimethylethanolamine is commonly referred to as 2-(dimethylamino)ethanol, Dimethylethanolamine (DMAE) or dimethylethanolamine (DMEA). These are organic compounds containing an alkylamine group. It holds tertiary amine and primary alcohol groups as functional groups. It has been also used as an ingredient in skin care, and in cognitive function- and mood-enhancing products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032231 (Dimethylethanolamine)

  Mrv1652305271900102D          

  6  5  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
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3D MOL for HMDB0032231 (Dimethylethanolamine)

HMDB0032231
     RDKit          3D
Dimethylethanolamine
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.2498   -1.1522    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412    0.0834   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5408    1.1889   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205    0.3746    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -0.5632   -0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9422   -0.2642    0.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161   -0.9189    0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8008   -1.6037   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5495   -1.8952    0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0787    2.0225    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8728    1.5116   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    0.8640    0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5287    0.3815    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9423    1.4007   -0.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117   -1.5743    0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7994   -0.4907   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987    0.6352    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
M  END
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3D SDF for HMDB0032231 (Dimethylethanolamine)

  Mrv1652305271900102D          

  6  5  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032231

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCO

> <INCHI_IDENTIFIER>
InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3

> <INCHI_KEY>
UEEJHVSXFDXPFK-UHFFFAOYSA-N

> <FORMULA>
C4H11NO

> <MOLECULAR_WEIGHT>
89.1362

> <EXACT_MASS>
89.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
10.496441263044256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(dimethylamino)ethan-1-ol

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-0.4999325463333331

> <ALOGPS_LOGS>
1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.594407934501302

> <JCHEM_PKA_STRONGEST_BASIC>
9.028747302274892

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
26.280399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylaminoethanol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0032231 (Dimethylethanolamine)

HMDB0032231
     RDKit          3D
Dimethylethanolamine
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.2498   -1.1522    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412    0.0834   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5408    1.1889   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205    0.3746    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -0.5632   -0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9422   -0.2642    0.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161   -0.9189    0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8008   -1.6037   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5495   -1.8952    0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0787    2.0225    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8728    1.5116   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    0.8640    0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5287    0.3815    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9423    1.4007   -0.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117   -1.5743    0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7994   -0.4907   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987    0.6352    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
M  END
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PDB for HMDB0032231 (Dimethylethanolamine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.850  -1.334   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    1    2    3                                                  
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0032231 (Dimethylethanolamine)

COMPND    HMDB0032231
HETATM    1  C1  UNL     1      -1.250  -1.152   0.042  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.641   0.083  -0.346  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.541   1.189  -0.180  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.621   0.375   0.251  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.719  -0.563  -0.239  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.942  -0.264   0.352  1.00  0.00           O  
HETATM    7  H1  UNL     1      -2.016  -0.919   0.828  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.801  -1.604  -0.833  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.549  -1.895   0.481  1.00  0.00           H  
HETATM   10  H4  UNL     1      -1.079   2.022   0.420  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.873   1.512  -1.180  1.00  0.00           H  
HETATM   12  H6  UNL     1      -2.412   0.864   0.450  1.00  0.00           H  
HETATM   13  H7  UNL     1       0.529   0.381   1.352  1.00  0.00           H  
HETATM   14  H8  UNL     1       0.942   1.401  -0.028  1.00  0.00           H  
HETATM   15  H9  UNL     1       1.412  -1.574   0.019  1.00  0.00           H  
HETATM   16  H10 UNL     1       1.799  -0.491  -1.340  1.00  0.00           H  
HETATM   17  H11 UNL     1       3.199   0.635   0.049  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4
CONECT    3   10   11   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6   17
END
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SMILES for HMDB0032231 (Dimethylethanolamine)

CN(C)CCO
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INCHI for HMDB0032231 (Dimethylethanolamine)

InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC4H11NO
Average Molecular Weight89.1362
Monoisotopic Molecular Weight89.084063979
IUPAC Name2-(dimethylamino)ethan-1-ol
Traditional Namedimethylaminoethanol
CAS Registry Number108-01-0
SMILES
CN(C)CCO
InChI Identifier
InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3
InChI KeyUEEJHVSXFDXPFK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-59 °CNot Available
Boiling Point134.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP-0.328 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13352
Phenol Explorer Compound IDNot Available
FooDB IDFDB009311
KNApSAcK IDNot Available
Chemspider ID13854944
KEGG Compound IDC04308
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethylethanolamine
METLIN IDNot Available
PubChem Compound7902
PDB IDNot Available
ChEBI ID271436
Food Biomarker OntologyNot Available
VMH IDM02758
MarkerDB IDNot Available
Good Scents IDrw1263531
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Su X, Cunningham MF, Jessop PG: Switchable viscosity triggered by CO2 using smart worm-like micelles. Chem Commun (Camb). 2013 Apr 4;49(26):2655-7. doi: 10.1039/c3cc37816k. [PubMed:23435477 ]
  2. (). EAFUS: Everything Added to Food in the United States.. .

Enzymes

Enzyme Details
1. Sulfotransferase family cytosolic 2B member 1
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Dimethylethanolamine → [2-(dimethylamino)ethoxy]sulfonic aciddetails
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Dimethylethanolamine → 6-[2-(dimethylamino)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails