2-Hydroxyestradiol-3-methyl ether (CHEM021620)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:08:28 UTC
Update Date2016-11-09 01:17:19 UTC
Accession NumberCHEM021620
Identification
Common Name2-Hydroxyestradiol-3-methyl ether
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Hydroxy-1,2,3-butanetricarboxylic acidChEBI
2-Hydroxy-1,2,3-butanetricarboxylateGenerator
2-MethylcitrateGenerator
(2S,3S)-2-MethylcitrateHMDB
2-Hydroxybutane-1,2,3-tricarboxylateHMDB
2-Hydroxybutane-1,2,3-tricarboxylic acidHMDB
2-Methylcitric acid, 3H-labeledHMDB
3-Carboxy-3-hydroxy-2-methylpentanedioic acidHMDB
Methylcitric acidHMDB
(17b)-3-Methoxy-estra-1,3,5(10)-triene-2,17-diolHMDB
2,3,17beta-Trihydroxy-1,3,5[10]-estratriene 2-methyl etherHMDB, ChEBI
2-Hydroxy-17b-estradiol 3-methyl etherHMDB
2-Hydroxy-3-methoxyestradiolHMDB, MeSH
2-Hydroxyestradiol 3-methyl etherHMDB
2-Hydroxyestradiol-3-methylether2-hydroxy-3-methoxy-17beta-estradiolHMDB
2H3MeOE2HMDB
3,17beta-Dihydroxy-2-methoxy-1,3,5[10]-estratrieneHMDB, ChEBI
3-Methoxy-1,3,5[10]-estratriene-2,17beta-diolHMDB, ChEBI
3-Methoxy-estra-1,3,5(10)-triene-2,17b-diolHMDB
3-O-Methyl-2-hydroxyestradiolHMDB, ChEBI
(17beta)-3-Methoxyestra-1(10),2,4-triene-2,17-diolChEBI
2-Hydroxy-3-methoxy-17beta-estradiolChEBI
(17b)-3-Methoxyestra-1(10),2,4-triene-2,17-diolGenerator
(17Β)-3-methoxyestra-1(10),2,4-triene-2,17-diolGenerator
2,3,17b-Trihydroxy-1,3,5[10]-estratriene 2-methyl etherGenerator
2,3,17Β-trihydroxy-1,3,5[10]-estratriene 2-methyl etherGenerator
2-Hydroxy-3-methoxy-17b-estradiolGenerator
2-Hydroxy-3-methoxy-17β-estradiolGenerator
3,17b-Dihydroxy-2-methoxy-1,3,5[10]-estratrieneGenerator
3,17Β-dihydroxy-2-methoxy-1,3,5[10]-estratrieneGenerator
3-Methoxy-1,3,5[10]-estratriene-2,17b-diolGenerator
3-Methoxy-1,3,5[10]-estratriene-2,17β-diolGenerator
2-OH-3-MeOE2MeSH, HMDB
Chemical FormulaC19H26O3
Average Molecular Mass302.408 g/mol
Monoisotopic Mass302.188 g/mol
CAS Registry Number5976-65-8
IUPAC Name(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol
Traditional Name(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C3
InChI IdentifierInChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-17(22-2)16(20)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
InChI KeyMMKYSUOJWFKECQ-SSTWWWIQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0099 g/LALOGPS
logP3.7ALOGPS
logP3.59ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.37 m³·mol⁻¹ChemAxon
Polarizability35.22 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-2190000000-e6c75d8a52a01c76343bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-2114900000-6f9fb5f37216642ee6daSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0197000000-2a3c454db7782949ce0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0692000000-19d694f42b9de8502d21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5590000000-3db0854af0439d356587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-fadd7d5b201334ca856eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0079000000-56f2013b7b78f5524223Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05pc-1090000000-cab4f6333da106d82f96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-4360bacaf95498925fe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-b5cab14cef0400c3f7b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-0090000000-2d9d4c650c6d9ed2dcf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-1d8e847a4bc26e5c1212Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbi-0694000000-cf79dc2520a1ddc06ac5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004u-2930000000-305ddbba055983ff8933Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000379
FooDB IDFDB021997
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID39369
BioCyc IDNot Available
METLIN ID5368
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID500
ChEBI ID30835
PubChem Compound ID515
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDECMDB00723
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
2. Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander. Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain. PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007101866 A2 20070913 CAN 147:363646 AN 2007:1033111
3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.
4. Busch M, Stein G, Poppitz W, Hein G, Muller A: Validated capillary gas chromatographic-mass spectrometric assay to determine 2-methylcitric acid I and II levels in human serum by using a pulsed splitless injection procedure. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 5;775(2):215-23.
5. Allen RH, Stabler SP, Savage DG, Lindenbaum J: Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency. Metabolism. 1993 Aug;42(8):978-88.
6. Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26.
7. Thompson GN, Chalmers RA: Increased urinary metabolite excretion during fasting in disorders of propionate metabolism. Pediatr Res. 1990 Apr;27(4 Pt 1):413-6.
8. Krawczyk H, Gradowska W: 1H NMR spectra of methylcitric acid in urine. J Inherit Metab Dis. 2007 Apr;30(2):263. Epub 2007 Feb 14.