Showing Compound 2-Hydroxyestradiol (FDB021962)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:56 UTC

Update date

2015-10-09 22:30:49 UTC

Primary ID

FDB021962

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Hydroxyestradiol

Description

2-Hydroxyestradiol, also known as 2-OH-e2 or ECS, 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. Based on a literature review a significant number of articles have been published on 2-Hydroxyestradiol.

CAS Number

362-05-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(17beta)-Estra-1,3,5(10)-triene-2,3,17-triol	ChEBI
2-Hydroxyestradiol-17beta	ChEBI
2-OH-e2	ChEBI
2-OH-Estradiol	ChEBI
(17b)-Estra-1,3,5(10)-triene-2,3,17-triol	Generator
(17Β)-estra-1,3,5(10)-triene-2,3,17-triol	Generator
2-Hydroxyestradiol-17b	Generator
2-Hydroxyestradiol-17β	Generator
(17b)-Estra-1,3, 5(10)-triene-2,3,17-triol	HMDB
(17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triol	HMDB
1,3,5(10)-Estratriene-2,3,17Beta-triol	HMDB
17beta-2-Hydroxyestradiol	HMDB
2,3,17b-Trihydroxyestra-1,3,5(10)-triene	HMDB
2-Hydroxy-17beta-estradiol	HMDB
2-Hydroxy-estradiol	HMDB
ECS	HMDB
Estra-1,3,5 (10)-triene-2,3,17.beta.-triol	HMDB
Estra-1,3,5(10)-triene-2,3,17-beta-triol	HMDB
Estra-1,3,5(10)-triene-2,3,17-triol (acd/name 4.0)	HMDB
Estra-1,3,5(10)-triene-2,3,17b-triol	HMDB
Estra-1,3,5(10)-triene-2,3,17beta-triol	HMDB
2-Hydroxyestradiol-17 alpha	HMDB
2-Hydroxyestradiol-17 beta	HMDB
2-Hydroxyestradiol, (17alpha)-isomer	HMDB
2-Hydroxyestradiol, 4-(14)C-labeled	HMDB
(17β)-estra-1,3,5(10)-triene-2,3,17-triol	Generator
1,3,5(10)-estratriene-2,3,17Beta-triol	hmdb
2-hydroxy-17beta-estradiol	hmdb
2-hydroxy-estradiol	hmdb
2-Hydroxyestradiol	hmdb
estra-1,3,5(10)-triene-2,3,17-triol (ACD/Name 4.0)	hmdb
estra-1,3,5(10)-triene-2,3,17beta-triol	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	3.39	ALOGPS
logP	3.44	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.89 m³·mol⁻¹	ChemAxon
Polarizability	33.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H24O3

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

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

Isomeric 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

Average Molecular Weight

288.3814

Monoisotopic Molecular Weight

288.172544634

Classification

Description

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

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:28744 )
2-hydroxy steroid (CHEBI:28744 )
C18 steroids (estrogens) and derivatives (C05301 )
Estrane and derivatives (C05301 )
C18 steroids (estrogens) and derivatives (LMST02010027 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Urine

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	2-Hydroxyestradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adr-2490000000-7e8a9e3990faceb5f6d0	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002u-1002900000-79ac7707883246949511	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxyestradiol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00ei-2950000000-326e2d3fee4fb8b3ca6c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-2910000000-553a7988f4c2019ec5d5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f96-8975000000-eef1fcf44ed6a27f53a9	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0190000000-0e1c17e32d9c1e4063eb	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0790000000-01416dcd9eea3747d3c5	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-6970000000-d27a7add654c423ec534	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-805faf5743eec20547cb	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-c39e06f8fdeeb111e97f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-1190000000-36538cb7b1a03d7b2ff7	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-572916cfebc6538c52d0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01w0-0490000000-7a41b9ec75d4c7c28c73	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-3910000000-4dd2fe1697c6e685073e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-843a74fabb1d0eb512a1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-40c60966bb1ce4624953	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-1009-0090000000-1c821729dedb3f0fecbe	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		Spectrum