NAV

2-Hydroxyestradiol

Identification

Generic Name
2-Hydroxyestradiol
DrugBank Accession Number
DB07706
Background

2-Hydroxyestradiol is classified as an endogenous steroid, catechol estrogen, and metabolite of estradiol. It is also a positional isomer of estriol. 1

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 288.3814
Monoisotopic: 288.172544634
Chemical Formula
C18H24O3
Synonyms
  • (17β)-estra-1,3,5(10)-triene-2,3,17-triol
  • 2-hydroxy-17beta-estradiol
  • 2-hydroxy-17β-estradiol
  • 2-Hydroxyestradiol-17beta
  • 2-OH-Estradiol
External IDs
  • BRN 2219367
  • NSC-61711
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAdenylate cyclaseNot AvailableArthrospira platensis
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
EntacaponeThe metabolism of 2-Hydroxyestradiol can be decreased when combined with Entacapone.
OpicaponeThe metabolism of 2-Hydroxyestradiol can be decreased when combined with Opicapone.
Testosterone propionateThe metabolism of 2-Hydroxyestradiol can be decreased when combined with Testosterone propionate.
TolcaponeThe metabolism of 2-Hydroxyestradiol can be decreased when combined with Tolcapone.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-hydroxysteroids / 17-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Cyclic alcohols and derivatives / Polyols / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 17-hydroxysteroid / 2-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aromatic homopolycyclic compound / Benzenoid / Cyclic alcohol / Estrogen-skeleton / Hydrocarbon derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
17beta-hydroxy steroid, 2-hydroxy steroid (CHEBI:28744) / C18 steroids (estrogens) and derivatives, Estrane and derivatives (C05301) / C18 steroids (estrogens) and derivatives (LMST02010027)
Affected organisms
Not Available

Chemical Identifiers

UNII
AYU2L67YUU
CAS number
362-05-0
InChI Key
DILDHNKDVHLEQB-XSSYPUMDSA-N
InChI
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
IUPAC Name
(1S,3aS,3bR,9bS,11aS)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7,8-triol
SMILES
[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=C(C=C(O)C(O)=C4)[C@@]3([H])CC[C@]12C

References

General References
  1. Zhu BT, Conney AH: Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis. 1998 Jan;19(1):1-27. [Article]
Human Metabolome Database
HMDB0000338
KEGG Compound
C05301
PubChem Compound
247304
PubChem Substance
99444177
ChemSpider
216475
BindingDB
50262140
ChEBI
28744
ChEMBL
CHEMBL467987
ZINC
ZINC000003815419
PDBe Ligand
ECS
Wikipedia
2-Hydroxyestradiol
PDB Entries
2bw7

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0511 mg/mLALOGPS
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 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity81.89 m3·mol-1Chemaxon
Polarizability33.08 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.7057
Caco-2 permeable+0.7591
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor INon-inhibitor0.9208
P-glycoprotein inhibitor IINon-inhibitor0.9805
Renal organic cation transporterNon-inhibitor0.8619
CYP450 2C9 substrateNon-substrate0.7536
CYP450 2D6 substrateNon-substrate0.7993
CYP450 3A4 substrateSubstrate0.6892
CYP450 1A2 substrateNon-inhibitor0.6618
CYP450 2C9 inhibitorNon-inhibitor0.9399
CYP450 2D6 inhibitorNon-inhibitor0.9619
CYP450 2C19 inhibitorNon-inhibitor0.7086
CYP450 3A4 inhibitorNon-inhibitor0.8932
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9152
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9147
BiodegradationNot ready biodegradable0.9811
Rat acute toxicity1.9758 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.948
hERG inhibition (predictor II)Inhibitor0.7684
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0adr-2490000000-7e8a9e3990faceb5f6d0
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-00ei-2950000000-326e2d3fee4fb8b3ca6c
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00di-2910000000-553a7988f4c2019ec5d5
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0f96-8975000000-eef1fcf44ed6a27f53a9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0090000000-df6ae3d72e3d98a52799
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-a066c7a393390b585b81
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-1e7a855cd399d54d05ba
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-1930000000-64a861a80f732c48ca76
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-029i-0090000000-b69b0b994e08e88aced7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06vi-0900000000-f83d2788ceb8f49f5799
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0090000000-df6ae3d72e3d98a52799
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-a066c7a393390b585b81
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-1930000000-64a861a80f732c48ca76
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-1e7a855cd399d54d05ba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-029i-0090000000-b69b0b994e08e88aced7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06vi-0900000000-f83d2788ceb8f49f5799
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.6132921
predicted
DarkChem Lite v0.1.0
[M-H]-178.5475921
predicted
DarkChem Lite v0.1.0
[M-H]-180.35167
predicted
DeepCCS 1.0 (2019)
[M-H]-177.6132921
predicted
DarkChem Lite v0.1.0
[M-H]-178.5475921
predicted
DarkChem Lite v0.1.0
[M-H]-180.35167
predicted
DeepCCS 1.0 (2019)
[M+H]+177.6170921
predicted
DarkChem Lite v0.1.0
[M+H]+179.5280921
predicted
DarkChem Lite v0.1.0
[M+H]+182.74725
predicted
DeepCCS 1.0 (2019)
[M+H]+177.6170921
predicted
DarkChem Lite v0.1.0
[M+H]+179.5280921
predicted
DarkChem Lite v0.1.0
[M+H]+182.74725
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.9926921
predicted
DarkChem Lite v0.1.0
[M+Na]+178.5962921
predicted
DarkChem Lite v0.1.0
[M+Na]+188.65977
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.9926921
predicted
DarkChem Lite v0.1.0
[M+Na]+178.5962921
predicted
DarkChem Lite v0.1.0
[M+Na]+188.65977
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Adenylate cyclase
Kind
Protein
Organism
Arthrospira platensis
Pharmacological action
Unknown
General Function
Phosphorelay sensor kinase activity
Specific Function
Not Available
Gene Name
cyaC
Uniprot ID
O32393
Uniprot Name
Adenylate cyclase
Molecular Weight
133922.415 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:25 / Updated at June 12, 2020 16:52