Livestock Metabolome Database: Showing metabocard for Cortexolone (LMDB00005)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:22:11 UTC

Update Date

2016-07-20 20:54:13 UTC

Lmdb

LMDB00005

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cortexolone

Description

Cortexolone, also known as cortodoxone or 11 deoxycortisol, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, cortexolone is considered to be a steroid lipid molecule. Cortexolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cortexolone is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
11-Desoxy-17-hydroxycorticosterone	ChEBI
Cortodoxone	ChEBI
Reichstein substance S	HMDB
Substance S, reichstein's	HMDB
11 Deoxycortisol	HMDB
11 Desoxycortisol	HMDB
11 Desoxycortisone	HMDB
S, Reichstein's substance	HMDB
11-Desoxycortisol	HMDB
11-Desoxycortisone	HMDB
Reichsteins substance S	HMDB
11-Deoxycortisol	HMDB
SK&F 3050	HMDB
Reichstein's substance S	HMDB
11-Deoxy-17-hydroxycorticosterone	HMDB
11-Deoxyhydrocortisone	HMDB
11-Desoxyhydrocortisone	HMDB
17,21-Dihydroxy-4-pregnene-3,20-dione	HMDB
17,21-Dihydroxypregn-4-ene-3,20-dione	HMDB
17,21-Dihydroxyprogesterone	HMDB
17-Hydroxy-11-deoxycorticosterone	HMDB
17alpha-Hydroxycortexone	HMDB
20-Dione 17,21-dihydroxypregn-4-ene-3	HMDB
4-Pregnene-17alpha,21-diol-3,20-dione	HMDB
Compound S	HMDB
11-Deoxy-17-hydrocorticosterone	HMDB
11-Deoxycortisone	HMDB
11-Desoxy-17α-hydroxycorticosterone	HMDB
11-Desoxy-17alpha-hydroxycorticosterone	HMDB
17,21-Dihydroxypregn-4-en-3,20-dione	HMDB
17Α,21-dihydroxy-4-pregnen-3,20-dione	HMDB
17Α,21-dihydroxypregn-4-ene-3,20-dione	HMDB
17Α,21-dihydroxyprogesterone	HMDB
17Α-hydroxycortexone	HMDB
4-Pregnen-17α,21-diol-3,20-dione	HMDB
4-Pregnene-17α,21-diol-3,20-dione	HMDB
17alpha,21-Dihydroxy-4-pregnen-3,20-dione	HMDB
17alpha,21-Dihydroxypregn-4-ene-3,20-dione	HMDB
17alpha,21-Dihydroxyprogesterone	HMDB
4-Pregnen-17alpha,21-diol-3,20-dione	HMDB
Cortexolone	MeSH

Chemical Formula

C₂₁H₃₀O₄

Average Molecular Weight

346.4605

Monoisotopic Molecular Weight

346.214409448

IUPAC Name

(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

152-58-9

SMILES

[H]C12CC[C@](O)(C(=O)CO)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16?,17?,19+,20+,21+/m1/s1

InChI Key

WHBHBVVOGNECLV-HMGFGKNBSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

21-hydroxysteroid
Progestogin-skeleton
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

glucocorticoid (CHEBI:28324 )
deoxycortisol (CHEBI:28324 )
Glucocorticoids (C05488 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05488 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030086 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.79	ALOGPS
logP	2.58	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.81 m³·mol⁻¹	ChemAxon
Polarizability	38.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 MEOX; 2 TMS)	splash10-0fau-4920000000-b369d2b097d724e4d6d6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4j-3931000000-0d5b4b35af4fb7259e0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4j-3931000000-0d5b4b35af4fb7259e0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-3a7012051ab6d4bf0562	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052b-7954000000-8b08129e96f27aa17d97	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-42c6be6599289f724a27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052b-6900000000-e4a3639328e2024d0e8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0009000000-bb32ffe5ad4a80ab7c5a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0390000000-d6fdb36b0e90c40b94cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0029000000-4461b817ffbd52446693	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0cfs-0198000000-95e4ea654010492c731e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01c9-0390000000-2c12ac25b2d03a951073	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0019000000-8ffa4f9a93205a223d67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-3089000000-630c1ceb5066f51ae904	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6091000000-520f7455eb4f28362eb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-6e67f0e99b733343d1e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08i0-0901000000-78c126f772ed1698f472	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002g-3930000000-d7d52250ebc31a93ab06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01pa-0049000000-bba8b14791a1510eb866	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0096000000-364c61e7a9193d6a16fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-0090000000-96af9df83c9954436093	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000015

FooDB ID

FDB021872

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

45914

BioCyc ID

Not Available

METLIN ID

5088

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB24010

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

White PC, Dupont J, New MI, Leiberman E, Hochberg Z, Rosler A: A mutation in CYP11B1 (Arg-448----His) associated with steroid 11 beta-hydroxylase deficiency in Jews of Moroccan origin. J Clin Invest. 1991 May;87(5):1664-7. [2022736 ]

Showing metabocard for Cortexolone (LMDB00005)

Structure for LMDB00005 (Cortexolone)