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Human Metabolome Database Version 3.5

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Showing metabocard for 2-Hydroxyestradiol (HMDB00338)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:21 -0700
HMDB ID HMDB00338
Secondary Accession Numbers
  • HMDB03962
Metabolite Identification
Common Name 2-Hydroxyestradiol
Description 2-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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (17b)-Estra-1,3, 5(10)-triene-2,3,17-triol
  2. (17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triol
  3. (17beta)-Estra-1,3,5(10)-triene-2,3,17-triol
  4. 1,3,5(10)-Estratriene-2,3,17Beta-triol
  5. 17beta-2-Hydroxyestradiol
  6. 2,3,17b-Trihydroxyestra-1,3,5(10)-triene
  7. 2-Hydroxy-17beta-estradiol
  8. 2-Hydroxy-estradiol
  9. 2-Hydroxyestradiol
  10. 2-OH-Estradiol
  11. ECS
  12. Estra-1,3,5 (10)-triene-2,3,17.beta.-triol
  13. Estra-1,3,5(10)-triene-2,3,17-beta-triol
  14. Estra-1,3,5(10)-triene-2,3,17-triol (ACD/Name 4.0)
  15. Estra-1,3,5(10)-triene-2,3,17b-triol
  16. Estra-1,3,5(10)-triene-2,3,17beta-triol
Chemical Formula C18H24O3
Average Molecular Weight 288.3814
Monoisotopic Molecular Weight 288.172544634
IUPAC Name (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-4,5,14-triol
Traditional IUPAC Name 2-hydroxyestradiol
CAS Registry Number 362-05-0
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 Key DILDHNKDVHLEQB-XSSYPUMDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Estrogens and Derivatives
Other Descriptors
  • 2-hydroxy steroid(ChEBI)
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • C18 steroids (estrogens) and derivatives(KEGG)
  • C18 steroids (estrogens) and derivatives(Lipidmaps)
  • Estrane and derivatives(KEGG)
  • Hydroxysteroids
Substituents
  • 1,2 Diphenol
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Phenanthrene
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
  • Sesquiterpene Backbone
  • Tetralin
Direct Parent Estrogens and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 190 - 191 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.051 g/L ALOGPS
LogP 3.39 ALOGPS
LogP 3.44 ChemAxon
LogS -3.75 ALOGPS
pKa (strongest acidic) 9.67 ChemAxon
pKa (strongest basic) -0.88 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 60.69 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 81.89 ChemAxon
Polarizability 33.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.0016 +/- 0.0014 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021962
KNApSAcK ID Not Available
Chemspider ID 216475 Link_out
KEGG Compound ID C05301 Link_out
BioCyc ID 2-HYDROXY-ESTRADIOL Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00338 Link_out
Metagene Link HMDB00338 Link_out
METLIN ID 5327 Link_out
PubChem Compound 247304 Link_out
PDB ID ECS Link_out
ChEBI ID 28744 Link_out
References
Synthesis Reference Kiuru, 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 Link_out
  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 Link_out
Enzymes
Name: Protein arginine N-methyltransferase 3
Reactions:
    Gene Name: PRMT3
    Uniprot ID: O60678 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytochrome P450 1B1
    Reactions:
    • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
    Gene Name: CYP1B1
    Uniprot ID: Q16678 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA