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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000343
Secondary Accession Numbers
  • HMDB00343
Metabolite Identification
Common Name2-Hydroxyestrone
Description2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol. 2-Hydroxyestrone 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-Hydroxyestrone is considered to be a steroid molecule. It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies. 2-OHE1 is the most abundant catechol estrogen in the body. 2-Hydroxyestrone is found in all vertebrates. Vertebrates, especially mammals, metabolizes estrogen into two major pathways and one minor. The two major pathways lead to 2-hydroxyestrone and 16a-hydroxyestrone (2-OHE1 and 16a OHE1, respectively). The minor pathway leads to 4-hydroxyestrone (4-OHE1). 2a-hydroxyestrone is considered to be the good steroid metabolite (PMID: 8943806 ) as 2-hydroxyestrone does not stimulate cell growth and it blocks the action of stronger estrogens that may be carcinogenic. 2-hydroxyestrone is not significantly uterotrophic, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16a-hydroxyestrone, estriol, 4-hydroxyestradiol, and 4-hydroxyestrone all are. A low urinary ratio of 2-hydroxyestrone to 16-alpha-hydroxyestrone is a strong predictor of breast cancer risk among women (PMID: 19502596 ).
Structure
Data?1582752125
Synonyms
ValueSource
2,3-Dihydroxyestra-1,3,5(10)-trien-17-oneHMDB
2-OHE1HMDB
CatecholestroneHMDB
2-Hydroxyestrone, 4-(14)C-labeledMeSH, HMDB
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
Traditional Name(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
CAS Registry Number362-06-1
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3
InChI Identifier
InChI=1S/C18H22O3/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/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1
InChI KeySWINWPBPEKHUOD-JPVZDGGYSA-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-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketone
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP3.03ALOGPS
logP4.01ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.06 m³·mol⁻¹ChemAxon
Polarizability32.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.9131661259
DarkChem[M-H]-162.51731661259
AllCCS[M+H]+170.18332859911
AllCCS[M-H]-175.80732859911
DeepCCS[M-2H]-210.29930932474
DeepCCS[M+Na]+185.49130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxyestrone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C33682.2Standard polar33892256
2-Hydroxyestrone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C32797.2Standard non polar33892256
2-Hydroxyestrone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C32996.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxyestrone,1TMS,isomer #1C[C@]12CC[C@@H]3C4=CC(O)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O2832.0Semi standard non polar33892256
2-Hydroxyestrone,1TMS,isomer #2C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CCC2=O2818.9Semi standard non polar33892256
2-Hydroxyestrone,1TMS,isomer #3C[C@]12CC[C@@H]3C4=CC(O)=C(O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C2770.8Semi standard non polar33892256
2-Hydroxyestrone,2TMS,isomer #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]1CCC2=O2866.8Semi standard non polar33892256
2-Hydroxyestrone,2TMS,isomer #2C[C@]12CC[C@@H]3C4=CC(O)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C2772.8Semi standard non polar33892256
2-Hydroxyestrone,2TMS,isomer #3C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C2743.1Semi standard non polar33892256
2-Hydroxyestrone,3TMS,isomer #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=C2O[Si](C)(C)C2752.2Semi standard non polar33892256
2-Hydroxyestrone,3TMS,isomer #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=C2O[Si](C)(C)C2726.3Standard non polar33892256
2-Hydroxyestrone,3TMS,isomer #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=C2O[Si](C)(C)C2953.2Standard polar33892256
2-Hydroxyestrone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC23108.4Semi standard non polar33892256
2-Hydroxyestrone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]123100.7Semi standard non polar33892256
2-Hydroxyestrone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O)=C(O)C=C4[C@H]3CC[C@]12C3045.8Semi standard non polar33892256
2-Hydroxyestrone,2TBDMS,isomer #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(=O)CC[C@H]3[C@@H]1CC23393.7Semi standard non polar33892256
2-Hydroxyestrone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C4[C@H]3CC[C@]12C3270.5Semi standard non polar33892256
2-Hydroxyestrone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C3241.9Semi standard non polar33892256
2-Hydroxyestrone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C3410.4Semi standard non polar33892256
2-Hydroxyestrone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C3306.1Standard non polar33892256
2-Hydroxyestrone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C3282.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vr-1980000000-fe43c8c5b3a4d07200c92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (2 TMS) - 70eV, Positivesplash10-016r-5449800000-4e55823f57ec07ec09132017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyestrone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0w2i-0798000000-41a67b9322f4b24283722012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyestrone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0f92-1920000000-1852b9bae72a1d8a9dc82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyestrone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0zfs-2930000000-5911e48b958d80b00d922012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Positive-QTOFsplash10-000i-0190000000-644377b19800b89d92e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Positive-QTOFsplash10-0a4r-0790000000-1a42c791a4695a613eac2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Positive-QTOFsplash10-0zfr-6690000000-645e51e9feba8eee90e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Negative-QTOFsplash10-000i-0090000000-42c0dd5f87119fd72c442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Negative-QTOFsplash10-000i-0090000000-6509e54bf81b0caae5512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Negative-QTOFsplash10-05mo-1090000000-ff9544e7658c8bae039d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Positive-QTOFsplash10-000i-0090000000-c6a01b40f4853dcb1f7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Positive-QTOFsplash10-07br-0590000000-21461e356ecdcb3c08c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Positive-QTOFsplash10-0200-1910000000-030e5b518db4e2ad41fd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Negative-QTOFsplash10-000i-0090000000-fcaf0435bbf678a207f72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Negative-QTOFsplash10-000i-0090000000-3a4481ab24130f65a8932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Negative-QTOFsplash10-0kor-0190000000-13b24a7b3a65583707422021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)2012-12-04Wishart LabView Spectrum
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
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00024 (0.00017-0.00033) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00017 (0.00015-0.00022) uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0001 (0.000070-0.00013) uMChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.0015 +/- 0.0013 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00052 (0.00036-0.00076) uMAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed:663967 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021966
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05298
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Hydroxyestrone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID1156
Food Biomarker OntologyNot Available
VMH IDC05298
MarkerDB IDMDB00000149
Good Scents IDNot Available
References
Synthesis ReferenceKovacs, Katalin; Rakonczay, Z.; Matkovics, B. Steroids. XXIII. Synthesis of 2- and 4-hydroxy and 2,4-dihydroxy derivatives of estrone and estradiol. Acta Physica et Chemica (1973), 19(3), 287-90.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brooks JD, Ward WE, Lewis JE, Hilditch J, Nickell L, Wong E, Thompson LU: Supplementation with flaxseed alters estrogen metabolism in postmenopausal women to a greater extent than does supplementation with an equal amount of soy. Am J Clin Nutr. 2004 Feb;79(2):318-25. [PubMed:14749240 ]
  2. Xu X, Veenstra TD, Fox SD, Roman JM, Issaq HJ, Falk R, Saavedra JE, Keefer LK, Ziegler RG: Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2005 Oct 15;77(20):6646-54. [PubMed:16223252 ]
  3. Numazawa M, Kimura K, Nagaoka M, Kambegawa A: Radioimmunoassay of 2-hydroxyesterone using antisera raised against antigenic complexes obtained by convenient methods. Chem Pharm Bull (Tokyo). 1989 Jun;37(6):1561-3. [PubMed:2776239 ]
  4. Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed:663967 ]
  5. Xu X, Keefer LK, Waterhouse DJ, Saavedra JE, Veenstra TD, Ziegler RG: Measuring seven endogenous ketolic estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2004 Oct 1;76(19):5829-36. [PubMed:15456304 ]
  6. Bradlow HL, Telang NT, Sepkovic DW, Osborne MP: 2-hydroxyestrone: the 'good' estrogen. J Endocrinol. 1996 Sep;150 Suppl:S259-65. [PubMed:8943806 ]
  7. Im A, Vogel VG, Ahrendt G, Lloyd S, Ragin C, Garte S, Taioli E: Urinary estrogen metabolites in women at high risk for breast cancer. Carcinogenesis. 2009 Sep;30(9):1532-5. doi: 10.1093/carcin/bgp139. Epub 2009 Jun 5. [PubMed:19502596 ]

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-Hydroxyestrone + S-Adenosylmethionine → 2-Methoxyestrone + S-Adenosylhomocysteinedetails