Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2020-06-03 16:21:17 UTC
Update Date2021-10-01 18:15:03 UTC
HMDB IDHMDB0240650
Secondary Accession NumbersNone
Metabolite Identification
Common NameEctoine
Descriptionectoine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. ectoine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on ectoine.
Structure
Data?1591302231
Synonyms
ValueSource
(+)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acidChEBI
L-EctoineChEBI
(4S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylateKegg
(+)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylateGenerator
(4S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acidGenerator
1,4,5,6-tetrahydro-2-Methyl-4-pyrimidinecarboxylic acidMeSH, HMDB
EctoinMeSH, HMDB
(4S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acidHMDB
(4S)-3,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acidHMDB
(S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acidHMDB
EctoineHMDB
Pyrostatin BHMDB
Pyrostatine BHMDB
Chemical FormulaC6H10N2O2
Average Molecular Weight142.1558
Monoisotopic Molecular Weight142.074227574
IUPAC Name(4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Traditional Nameectoine
CAS Registry Number96702-03-3
SMILES
CC1=NCC[C@H](N1)C(O)=O
InChI Identifier
InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1
InChI KeyWQXNXVUDBPYKBA-YFKPBYRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Hydropyrimidine carboxylic acid derivative
  • Hydropyrimidine
  • 1,4,5,6-tetrahydropyrimidine
  • Imidolactam
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(-0.23) g/LALOGPS
logP10(-2.5) g/LChemAxon
logS10(-1.1) g/LALOGPS
pKa (Strongest Acidic)2.75ChemAxon
pKa (Strongest Basic)10.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.04 m³·mol⁻¹ChemAxon
Polarizability14.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ectoine,1TMS,#1CC1=NCC[C@@H](C(=O)O[Si](C)(C)C)N11412.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Ectoine,1TMS,#2CC1=NCC[C@@H](C(=O)O)N1[Si](C)(C)C1564.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Ectoine,1TBDMS,#1CC1=NCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N11652.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Ectoine,1TBDMS,#2CC1=NCC[C@@H](C(=O)O)N1[Si](C)(C)C(C)(C)C1776.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ectoine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ectoine 50V, Positive-QTOFsplash10-0007-5900000000-f2bf01bf09de376591c42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ectoine 50V, Negative-QTOFsplash10-0006-0900000000-0df36d79991c1fa4a82c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ectoine 10V, Positive-QTOFsplash10-0006-2900000000-461b411f6b09403b56942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ectoine 20V, Positive-QTOFsplash10-0002-9100000000-07a8428071aadde90d222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ectoine 40V, Positive-QTOFsplash10-0aba-9000000000-e10d9e3345119cd297cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ectoine 10V, Negative-QTOFsplash10-0006-0900000000-45064a2e85c935d3a95b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ectoine 20V, Negative-QTOFsplash10-0006-8900000000-6dd41398500425af5df02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ectoine 40V, Negative-QTOFsplash10-0006-9000000000-fc9f75ff6724724b27cd2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00053168
Chemspider ID112069
KEGG Compound IDC06231
BioCyc IDECTOINE
BiGG IDNot Available
Wikipedia LinkEctoine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27592
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1731791
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang T, Creek DJ, Barrett MP, Blackburn G, Watson DG: Evaluation of coupling reversed phase, aqueous normal phase, and hydrophilic interaction liquid chromatography with Orbitrap mass spectrometry for metabolomic studies of human urine. Anal Chem. 2012 Feb 21;84(4):1994-2001. doi: 10.1021/ac2030738. Epub 2012 Feb 1. [PubMed:22409530 ]
  2. Mair RD, Sirich TL, Plummer NS, Meyer TW: Characteristics of Colon-Derived Uremic Solutes. Clin J Am Soc Nephrol. 2018 Sep 7;13(9):1398-1404. doi: 10.2215/CJN.03150318. Epub 2018 Aug 7. [PubMed:30087103 ]

Enzymes

General function:
Not Available
Specific function:
Catalyzes the circularization of gamma-N-acetyl-alpha,gamma-diaminobutyric acid (ADABA) to ectoine (1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid), which is an excellent osmoprotectant.
Gene Name:
ECTC
Uniprot ID:
B4R981
Molecular weight:
14628.525