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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:16:07 UTC
HMDB IDHMDB0000338
Secondary Accession Numbers
  • HMDB00338
  • HMDB03962
Metabolite Identification
Common Name2-Hydroxyestradiol
Description2-Hydroxyestradiol is generated from estradiol by a Cytochrome P450. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. It inhbits catechol-O-methyltransferase (COMT) activity. Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neutransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688 ).
Structure
Thumb
Synonyms
ValueSource
(17beta)-Estra-1,3,5(10)-triene-2,3,17-triolChEBI
2-Hydroxyestradiol-17betaChEBI
2-OH-e2ChEBI
2-OH-EstradiolChEBI
(17b)-Estra-1,3,5(10)-triene-2,3,17-triolGenerator
(17β)-estra-1,3,5(10)-triene-2,3,17-triolGenerator
2-Hydroxyestradiol-17bGenerator
2-Hydroxyestradiol-17βGenerator
(17b)-Estra-1,3, 5(10)-triene-2,3,17-triolHMDB
(17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triolHMDB
1,3,5(10)-Estratriene-2,3,17Beta-triolHMDB
17beta-2-HydroxyestradiolHMDB
2,3,17b-Trihydroxyestra-1,3,5(10)-trieneHMDB
2-Hydroxy-17beta-estradiolHMDB
2-Hydroxy-estradiolHMDB
ECSHMDB
Estra-1,3,5 (10)-triene-2,3,17.beta.-triolHMDB
Estra-1,3,5(10)-triene-2,3,17-beta-triolHMDB
Estra-1,3,5(10)-triene-2,3,17-triol (acd/name 4.0)HMDB
Estra-1,3,5(10)-triene-2,3,17b-triolHMDB
Estra-1,3,5(10)-triene-2,3,17beta-triolHMDB
2-Hydroxyestradiol-17 alphaMeSH
2-Hydroxyestradiol-17 betaMeSH
2-Hydroxyestradiol, (17alpha)-isomerMeSH
2-Hydroxyestradiol, 4-(14)C-labeledMeSH
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,5,14-triol
Traditional Name2-hydroxyestradiol
CAS Registry Number362-05-0
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3
InChI Identifier
InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
InChI KeyDILDHNKDVHLEQB-XSSYPUMDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point190 - 191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP3.39ALOGPS
logP3.44ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.89 m³·mol⁻¹ChemAxon
Polarizability33.06 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adr-2490000000-7e8a9e3990faceb5f6d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-002u-1002900000-79ac7707883246949511View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ei-2950000000-326e2d3fee4fb8b3ca6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2910000000-553a7988f4c2019ec5d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f96-8975000000-eef1fcf44ed6a27f53a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-0e1c17e32d9c1e4063ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0790000000-01416dcd9eea3747d3c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6970000000-d27a7add654c423ec534View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-805faf5743eec20547cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c39e06f8fdeeb111e97fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-1190000000-36538cb7b1a03d7b2ff7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0016 +/- 0.0014 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021962
KNApSAcK IDNot Available
Chemspider ID216475
KEGG Compound IDC05301
BioCyc ID2-HYDROXY-ESTRADIOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5327
PubChem Compound247304
PDB IDECS
ChEBI ID28744
References
Synthesis ReferenceKiuru, Paula S.; Wahala, Kristiina. Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol. Steroids (2003), 68(4), 373-375.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Takanashi K, Honma T, Kashiwagi T, Honjo H, Yoshizawa I: Detection and measurement of urinary 2-hydroxyestradiol 17-sulfate, a potential placental antioxidant during pregnancy. Clin Chem. 2000 Mar;46(3):373-8. [PubMed:10702524 ]
  2. Elce JS, Bird CE, Chandra J: Water-soluble products of the estrogens. Bile metabolites of 2-hydroxyestradiol-17beta in man. J Clin Endocrinol Metab. 1973 May;36(5):1027-30. [PubMed:4698236 ]
  3. Zhu BT, Conney AH: Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis. 1998 Jan;19(1):1-27. [PubMed:9472688 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
2-Hydroxyestradiol + S-Adenosylmethionine → 2-Methoxyestradiol + S-Adenosylhomocysteinedetails
General function:
Involved in protein methyltransferase activity
Specific function:
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:
PRMT3
Uniprot ID:
O60678
Molecular weight:
59902.7
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33