Cortisone

Details

• Internal ID: 0b081be1-8a2a-4c40-85c5-492917fd3cbf
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 21-hydroxysteroids
• IUPAC Name: (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
• SMILES (Canonical): CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4(C(=O)CO)O)C
• SMILES (Isomeric): C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C
• InChI: 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
• Popularity: 40,267 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.19367399 g/mol
• Topological Polar Surface Area (TPSA): 91.70 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 53-06-5
• Kendall's compound E
• Cortisate
• Cortistal
• Cortivite
• Andreson
• Cortisal
• Reichstein's substance FA
• Adrenalex
• Cortogen
• Reichstein Fa
• Wintersteiner's compound F
• 11-Dehydro-17-hydroxycorticosterone
• 17-Hydroxy-11-dehydrocorticosterone
• Cortandren
• Cortison
• Cortisona
• Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-
• 17,21-Dihydroxypregn-4-ene-3,11,20-trione
• Cortisonum
• Kortison
• 4-Pregnene-17alpha,21-diol-3,11,20-trione
• 17alpha-Hydroxy-11-dehydrocorticosterone
• NSC 9703
• 17alpha,21-Dihydroxy-4-pregnene-3,11,20-trione
• 17alpha,21-Dihydroxypregn-4-ene-3,11,20-trione
• Cortisonum [INN-Latin]
• Pregn-4-en-17alpha,21-diol-3,11,20-trione
• Cortisona [INN-Spanish]
• NSC-9703
• EINECS 200-162-4
• Kendall's compound
• [3H]-cortisone
• Prestwick_132
• UNII-V27W9254FZ
• DTXSID5022857
• CHEBI:16962
• AI3-52938
• V27W9254FZ
• delta(sup4)-pregnene-17alpha,21-diol-3,11,20-trione
• MLS000028540
• DTXCID102857
• [3H]cortisone
• NSC9703
• Cortisone (INN)
• SMR000058334
• CORTISONE [INN]
• Cortisonum (INN-Latin)
• 17.alpha.-Hydroxy-11-dehydrocorticosterone
• Cortisona (INN-Spanish)
• CORTISONE (USP-RS)
• CORTISONE [USP-RS]
• (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
• Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy
• Delta(4)-pregnene-17alpha,21-diol-3,11,20-trione
• Cortisone [INN:BAN]
• (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
• PREDNISONE IMPURITY A (EP IMPURITY)
• PREDNISONE IMPURITY A [EP IMPURITY]
• HYDROCORTISONE IMPURITY B (EP IMPURITY)
• HYDROCORTISONE IMPURITY B [EP IMPURITY]
• CAS-53-06-5
• Cortisone (TN)
• NCGC00095935-01
• Corlin (Salt/Mix)
• MFCD00003610
• Therapeutic Cortisone
• Cortelan (Salt/Mix)
• Ricortex (Salt/Mix)
• Cortadren (Salt/Mix)
• Scheroson (Salt/Mix)
• Cortisone, >=98%
• Opera_ID_541
• CORTISONE [MI]
• Prestwick0_000273
• Prestwick1_000273
• Prestwick2_000273
• Prestwick3_000273
• Spectrum5_002051
• CORTISONE [VANDF]
• bmse000663
• CORTISONE [WHO-DD]
• SCHEMBL4888
• CHEMBL1499
• Lopac0_000240
• BSPBio_000146
• Cortisonum 30 Special Order
• MLS001076142
• MLS001424269
• MLS002207137
• 17.alpha.,11,20-trione
• SPBio_002365
• Cortisone, 1mg/ml in Methanol
• BPBio1_000162
• GTPL5171
• BDBM13739
• H02AB10
• S01BA03
• Cortisone 0.1 mg/ml in Methanol
• HMS1568H08
• HMS2052A21
• HMS2095H08
• HMS2235P19
• HMS3260P21
• HMS3712H08
• Tox21_111539
• Tox21_301440
• Tox21_500240
• LMST02030090
• s5869
• AKOS015840096
• AKOS015894868
• Tox21_111539_1
• CCG-101143
• CS-5097
• DB14681
• LP00240
• NC00393
• SDCCGSBI-0050228.P002
• 4-Pregnene-17.alpha.,11,20-trione
• NCGC00023939-03
• NCGC00023939-04
• NCGC00023939-05
• NCGC00023939-06
• NCGC00023939-07
• NCGC00023939-08
• NCGC00023939-09
• NCGC00023939-11
• NCGC00023939-15
• NCGC00255108-01
• NCGC00260925-01
• Pregn-4-en-17.alpha.,11,20-trione
• AC-33118
• AS-11686
• HY-17461
• NCI60_042165
• EU-0100240
• C 2755
• C00762
• D07749
• D96089
• Pregn-4-ene-3,20-trione, 17,21-dihydroxy-
• 17,21-Dihydroxy-pregn-4-ene-3,11,20-trione
• .delta.(sup4)-pregnene-17.alpha.,11,20-trione
• 4-Pregnene-17.alpha.,21-diol-3,11,20-trione
• Q423185
• SR-01000000094
• Pregn-4-en-17.alpha.,21-diol-3,11,20-trione
• SR-01000000094-3
• W-105776
• 17.alpha.,21-Dihydroxy-4-pregnene-3,11,20-trione
• BRD-K43736954-001-03-3
• Cortisone, certified reference material, TraceCERT(R)
• WLN: L E5 B666 CV OV MUTJ A1 E1 FV1Q FQ
• .DELTA.4-pregnene-17.alpha.,21-diol-3,11,20-trione
• 17.alpha.,21.beta.-Dihydroxypregn-4-ene-3,11,20-trione
• (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
• Kendall's Compound E; 4-Pregnene-17alpha,21-diol-3,11,20-trione; Reichstein's Substance Fa
• UQC

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.6793	67.93%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8362	83.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9400	94.00%
OATP1B3 inhibitior	+	0.9613	96.13%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6852	68.52%
BSEP inhibitior	+	0.9071	90.71%
P-glycoprotein inhibitior	-	0.8621	86.21%
P-glycoprotein substrate	-	0.6570	65.70%
CYP3A4 substrate	+	0.7981	79.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9006	90.06%
CYP3A4 inhibition	-	0.8902	89.02%
CYP2C9 inhibition	-	0.9072	90.72%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.9406	94.06%
CYP2C8 inhibition	+	0.5598	55.98%
CYP inhibitory promiscuity	-	0.9095	90.95%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7360	73.60%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9726	97.26%
Skin irritation	+	0.6116	61.16%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.7634	76.34%
Human Ether-a-go-go-Related Gene inhibition	-	0.4670	46.70%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8843	88.43%
Acute Oral Toxicity (c)	III	0.7997	79.97%
Estrogen receptor binding	+	0.8512	85.12%
Androgen receptor binding	+	0.8856	88.56%
Thyroid receptor binding	+	0.7353	73.53%
Glucocorticoid receptor binding	+	0.9010	90.10%
Aromatase binding	+	0.8588	85.88%
PPAR gamma	-	0.7809	78.09%
Honey bee toxicity	-	0.8328	83.28%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9785	97.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	562.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.03%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	97.40%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.37%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.05%	97.25%
CHEMBL1871	P10275	Androgen Receptor	91.03%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.93%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.53%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.68%	98.95%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	83.69%	94.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.85%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.30%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.15%	91.19%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.21%	93.99%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.73%	89.05%
CHEMBL226	P30542	Adenosine A1 receptor	80.48%	95.93%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 222786
• LOTUS: LTS0084710
• wikiData: Q423185