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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-03-02 17:03:43 UTC
Update Date2017-12-07 02:32:19 UTC
HMDB IDHMDB0011727
Secondary Accession Numbers
  • HMDB11727
Metabolite Identification
Common NameBicine
Description. Bicine is a general purpose buffer for biological research. Useful pH range is 7.6 - 9.0. Its applications include: tissue culture,phosphorylation and photophosphorylation, fixative transmission electron microscopy, protein synthesis and preventing binding to non-receptor materials. It is a degradation product of alkanolamine and alkylalkanolamine solutions.
Structure
Thumb
Synonyms
ValueSource
Bicine bufferChEBI
BiceneHMDB
Bis(2-hydroxyethyl)glycineHMDB
Diethanol glycineHMDB
DiethylolglycineHMDB
DihydroxyethylglycineHMDB
N,N-(2-Dihydroxyethyl)glycineHMDB
N,N-(2-Hydroxyethyl)glycineHMDB
N,N-Bis(2-hydroxyethyl)-glycineHMDB
N,N-Bis(2-hydroxyethyl)glycineHMDB
N,N-Bis(2-hydroxyethyl)glycine]HMDB
N,N-Bis(beta-hydroxyethyl)glycineHMDB
N,N-Bis(hydroxyethyl)glycineHMDB
N,N-Di(2-hydroxyethyl)glycineHMDB
N,N-Dihydroxyethyl glycineHMDB
N,N-DihydroxyethylglycineHMDB
N,N-Bis(2-hydroxyethyl)glycine, monosodium saltMeSH
N,N-Bis(2-hydroxyethyl)glycine, sodium saltMeSH
Chemical FormulaC6H13NO4
Average Molecular Weight163.1717
Monoisotopic Molecular Weight163.084457909
IUPAC Name2-[bis(2-hydroxyethyl)amino]acetic acid
Traditional Namebicine
CAS Registry Number150-25-4
SMILES
OCCN(CCO)CC(O)=O
InChI Identifier
InChI=1S/C6H13NO4/c8-3-1-7(2-4-9)5-6(10)11/h8-9H,1-5H2,(H,10,11)
InChI KeyFSVCELGFZIQNCK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • 1,2-aminoalcohol
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Alkanolamine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility182 g/LALOGPS
logP-1.6ALOGPS
logP-4.4ChemAxon
logS0.05ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)7.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity38.66 m³·mol⁻¹ChemAxon
Polarizability16.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0590000000-0b4a6e303ad0b7aa8811View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-0950000000-13cea6f57c5544417311View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0590000000-0b4a6e303ad0b7aa8811View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-0950000000-13cea6f57c5544417311View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-9600000000-86746b520966dd484805View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0200-8493000000-3d4f043062d0b8998353View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0900000000-385f63e584e8574b09e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-2d0c20b213970b82d046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9300000000-588050ec6a52f9fe8805View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-cc0d32efa68c17b83343View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-fad830e28914ea85bdbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-db7eee00ece01cf87949View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03709
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028408
KNApSAcK IDNot Available
Chemspider ID8431
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBicine
METLIN IDNot Available
PubChem Compound8761
PDB IDBCN
ChEBI ID39066
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]