Bovine Metabolome Database: Showing metabocard for Cortisone (BMDB0002802)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:01:39 UTC

Update Date

2020-05-11 20:57:10 UTC

BMDB ID

BMDB0002802

Secondary Accession Numbers

BMDB02802

Metabolite Identification

Common Name

Cortisone

Description

Cortisonee, also known as cortisone or cortisone, 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, cortisonee is considered to be a steroid lipid molecule. Cortisonee exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Cortisonee participates in a number of enzymatic reactions, within cattle. In particular, Cortisonee can be biosynthesized from 17a,21-dihydroxy-5b-pregnane-3,11,20-trione; which is mediated by the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, Cortisonee, nadph, and hydrogen ion can be biosynthesized from cortisol and nadp through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2. In cattle, cortisonee is involved in the metabolic pathway called the steroidogenesis pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
11-Dehydro-17-hydroxycorticosterone	ChEBI
17-Hydroxy-11-dehydrocorticosterone	ChEBI
17alpha,21-Dihydroxy-4-pregnene-3,11,20-trione	ChEBI
4-Pregnene-17alpha,21-diol-3,11,20-trione	ChEBI
Cortison	ChEBI
Delta(4)-Pregnene-17alpha,21-diol-3,11,20-trione	ChEBI
Kendall's compound e	ChEBI
Kortison	ChEBI
Pregn-4-en-17alpha,21-diol-3,11,20-trione	ChEBI
Reichstein's substance fa	ChEBI
Wintersteiner's compound F	ChEBI
17a,21-Dihydroxy-4-pregnene-3,11,20-trione	Generator
17Α,21-dihydroxy-4-pregnene-3,11,20-trione	Generator
4-Pregnene-17a,21-diol-3,11,20-trione	Generator
4-Pregnene-17α,21-diol-3,11,20-trione	Generator
delta(4)-Pregnene-17a,21-diol-3,11,20-trione	Generator
Δ(4)-pregnene-17α,21-diol-3,11,20-trione	Generator
Pregn-4-en-17a,21-diol-3,11,20-trione	Generator
Pregn-4-en-17α,21-diol-3,11,20-trione	Generator
Δ(4)-pregnene-17a,21-diol-3,11,20-trione	HMDB
Andreson	HMDB
Anusol HC	HMDB
Balneol-HC	HMDB
beta-HC	HMDB
Colocort	HMDB
Compound e	HMDB
Corlin	HMDB
Cortadren	HMDB
Cortandren	HMDB
Cortef	HMDB
Cortef acetate	HMDB
Cortisal	HMDB
Cortisate	HMDB
Cortisone acetate	HMDB
Cortistal	HMDB
Cortivite	HMDB
Cortogen	HMDB
Cortone	HMDB
Cortril	HMDB
Dermacort	HMDB
Dricort	HMDB
Flexicort	HMDB
Florinef	HMDB
Fludrocortisone acetate	HMDB
Glycort	HMDB
Hemsol-HC	HMDB
Hi-cor	HMDB
Incortin	HMDB
Kendall'S compound	HMDB
Locoid	HMDB
Locoid lipocream	HMDB
Micort-HC	HMDB
Nogenic HC	HMDB
Orabase hca	HMDB
Pandel	HMDB
Prestwick_132	HMDB
Reichstein fa	HMDB
Scheroson	HMDB
Solu-cortef	HMDB
Stie-cort	HMDB
Texacort	HMDB
Westcort	HMDB
Adreson	HMDB
Cortone acetate	HMDB
17-Hydroxy-3,11,20-trioxopregn-4-en-21-yl acetate	HMDB

Chemical Formula

C₂₁H₂₈O₅

Average Molecular Weight

360.444

Monoisotopic Molecular Weight

360.193674006

IUPAC Name

(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione

Traditional Name

(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione

CAS Registry Number

53-06-5

SMILES

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

InChI Identifier

InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

InChI Key

MFYSYFVPBJMHGN-ZPOLXVRWSA-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

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:16962 )
17alpha-hydroxy steroid (CHEBI:16962 )
glucocorticoid (CHEBI:16962 )
20-oxo steroid (CHEBI:16962 )
11-oxo steroid (CHEBI:16962 )
21-hydroxy steroid (CHEBI:16962 )
C21-steroid (CHEBI:16962 )
Pregnane and derivatives [Fig] (C00762 )
Glucocorticoids (C00762 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C00762 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030090 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane
Myelin sheath

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	222 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 mg/mL at 25 °C	Not Available
LogP	1.47	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.98	ALOGPS
logP	1.66	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.47 m³·mol⁻¹	ChemAxon
Polarizability	38.95 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kf-2910000000-da435cee921dd7b9f8e6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kf-2910000000-da435cee921dd7b9f8e6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ai-5879000000-d8ce750671bf51b487e2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0f79-2918800000-ab308a6a5023c34bc22f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0009000000-5d34de066e82cc9f0a41	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-0900000000-24ec04976da03c3f9c77	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fdo-4900000000-d0880bfc6f3d80e4aa72	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03di-3940000000-16be8720b1c49cea9b06	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0009000000-6c22c083c2dfab97a299	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0109000000-48c96b3d1471c5cd6171	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-002r-0914000000-2466a9146383b4265e42	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0900000000-214430a00501054cc774	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-059j-1900000000-0e23516e07f0baf74c79	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0abj-1900000000-ad0282ab7188d9ec3dc1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0aba-3900000000-e36e464b157b3e6159f1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4j-5900000000-fe9092d76099e1e70a4e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0aou-6900000000-1b218b97a890ac7e8f45	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03fr-0049000000-3bd424d473bdadd2b9b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0039000000-fd181dfb87e1cbb8ab6f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0049000000-7633496a1a53bda21707	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0009000000-59db5e627634e4be3907	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0009000000-9781e204df305d722d2d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0009000000-0b5e40226163a1a334db	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0009000000-946472abc72d41b1633c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003u-0149000000-efb3f94efcbdfc468859	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5j-2392000000-d014016e46f2ae8b1bd1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-1c4a8c3698ff1bfa2bd9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-2029000000-82b546174619108311f8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-8093000000-47f7996c84edb1324aad	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane
Myelin sheath

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Placenta
Skeletal Muscle
Testis
Thyroid Gland

Pathways

Name	SMPDB/Pathwhiz	KEGG
Steroidogenesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Cortex	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Thyroid Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002802

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023065

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16962

References

Synthesis Reference

Ganis, Frank M.; Axelrod, Leonard R.; Miller, Leon L. The metabolism of hydrocortisone by kidney tissue in vitro. Journal of Biological Chemistry (1956), 218 841-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Cortisone (BMDB0002802)

Structure for BMDB0002802 (Cortisone)