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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:24 UTC
HMDB IDHMDB0000338
Secondary Accession Numbers
  • HMDB0003962
  • HMDB00338
  • HMDB03962
Metabolite Identification
Common Name2-Hydroxyestradiol
Description2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17beta-triol, is an endogenous steroid, catechol estrogen. 2-Hydroxyestradiol belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-hydroxyestradiol is considered to be a steroid molecule. It is a metabolite of estradiol, as well as a positional isomer of estriol. Transformation of estradiol to 2-hydroxyestradiol is a major metabolic pathway of estradiol in the liver. 2-Hydroxyestradiol is generated from estradiol via several cytochrome P450 enzymes. Specifically, CYP1A2 and CYP3A4 are the major enzymes catalyzing the 2-hydroxylation of estradiol. Conversion of estradiol into 2-hydroxyestradiol has been detected in the liver, uterus, breast, kidney, brain, and pituitary gland, as well as the placenta. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. 2-Hydroxyestradiol has approximately 7% and 11% of the affinity of estradiol at the estrogen receptors (ERs) ERalpha and ERbeta, respectively (PMID: 9048584 ). 2-Hydroxyestradiol is a catechol estrogen and in this regard bears some structural resemblance to the catecholamines dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline) (PMID: 447670 ). In accordance, 2-hydroxyestradiol has been found to interact with catecholamine systems. The steroid is known to compete with catecholamines for binding to catechol O-methyltransferase and tyrosine hydroxylase and to competitively inhibit these enzymes (PMID: 447670 ). Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neurotransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688 ).
Structure
Data?1582752124
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 alphaHMDB
2-Hydroxyestradiol-17 betaHMDB
2-Hydroxyestradiol, (17alpha)-isomerHMDB
2-Hydroxyestradiol, 4-(14)C-labeledHMDB
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol
Traditional Name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol
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
Description 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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190 - 191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP10(3.39) g/LALOGPS
logP10(3.44) g/LChemAxon
logS10(-3.8) g/LALOGPS
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
Polarizability33.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.13231661259
DarkChem[M-H]-160.76531661259
AllCCS[M+H]+171.83332859911
AllCCS[M-H]-176.13632859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxyestradiol,1TMS,#1C[C@]12CC[C@@H]3C4=CC(O)=C(O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2821.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,1TMS,#2C[C@]12CC[C@@H]3C4=CC(O)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O2810.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,1TMS,#3C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O2802.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,2TMS,#1C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2798.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,2TMS,#2C[C@]12CC[C@@H]3C4=CC(O)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2817.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,2TMS,#3C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O2805.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,3TMS,#1C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2820.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O)=C(O)C=C4[C@H]3CC[C@]12C3092.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC23100.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]123093.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,2TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC23369.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,2TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]123339.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,2TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC23336.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyestradiol,3TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC23535.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adr-2490000000-7e8a9e3990faceb5f6d02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (3 TMS) - 70eV, Positivesplash10-002u-1002900000-79ac77078832469495112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol 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 - 2-Hydroxyestradiol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00ei-2950000000-326e2d3fee4fb8b3ca6c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyestradiol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-2910000000-553a7988f4c2019ec5d52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyestradiol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0f96-8975000000-eef1fcf44ed6a27f53a92012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Positive-QTOFsplash10-00dr-0190000000-0e1c17e32d9c1e4063eb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Positive-QTOFsplash10-00dr-0790000000-01416dcd9eea3747d3c52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Positive-QTOFsplash10-0006-6970000000-d27a7add654c423ec5342017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Negative-QTOFsplash10-000i-0090000000-805faf5743eec20547cb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Negative-QTOFsplash10-000i-0090000000-c39e06f8fdeeb111e97f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Negative-QTOFsplash10-0596-1190000000-36538cb7b1a03d7b2ff72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Positive-QTOFsplash10-000i-0090000000-572916cfebc6538c52d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Positive-QTOFsplash10-01w0-0490000000-7a41b9ec75d4c7c28c732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Positive-QTOFsplash10-004j-3910000000-4dd2fe1697c6e685073e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Negative-QTOFsplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Negative-QTOFsplash10-000i-0090000000-40c60966bb1ce46249532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Negative-QTOFsplash10-1009-0090000000-1c821729dedb3f0fecbe2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB07706
Phenol Explorer Compound IDNot Available
FooDB IDFDB021962
KNApSAcK IDNot Available
Chemspider ID216475
KEGG Compound IDC05301
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Hydroxyestradiol
METLIN ID5327
PubChem Compound247304
PDB IDNot Available
ChEBI ID28744
Food Biomarker OntologyNot Available
VMH IDC05301
MarkerDB IDNot Available
Good Scents IDNot Available
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. Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. [PubMed:9048584 ]
  2. 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 ]
  3. 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 ]
  4. Zhu BT, Conney AH: Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis. 1998 Jan;19(1):1-27. [PubMed:9472688 ]
  5. Schaeffer JM, Hsueh AJ: 2-Hydroxyestradiol interaction with dopamine receptor binding in rat anterior pituitary. J Biol Chem. 1979 Jul 10;254(13):5606-8. [PubMed:447670 ]

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