Corticosterone

Details

• Internal ID: 3572501a-5472-4691-80d8-829112bfef93
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 21-hydroxysteroids
• IUPAC Name: (8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4C(=O)CO)C)O
• SMILES (Isomeric): C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C)O
• InChI: InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1
• InChI Key: OMFXVFTZEKFJBZ-HJTSIMOOSA-N
• Popularity: 43,882 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.50 g/mol
• Exact Mass: 346.21440943 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 50-22-6
• 17-Deoxycortisol
• Kendall's compound B
• Reichstein's substance H
• Corticosteron
• 11beta,21-Dihydroxyprogesterone
• (11beta)-11,21-Dihydroxypregn-4-ene-3,20-dione
• 11beta,21-Dihydroxy-4-pregnene-3,20-dione
• 11Beta,21-dihydroxypregn-4-ene-3,20-dione
• NSC-9705
• 4-Pregnene-11beta,21-diol-3,20-dione
• DTXSID6022474
• CHEBI:16827
• W980KJ009P
• (8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• DTXCID702474
• (8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-3-one
• RefChem:579253
• 200-019-6
• Reichstein's B
• 11-Hydroxycorticoaldosterone
• 11,21-Dihydroxyprogesterone
• MFCD00037715
• 11-beta,21-Dihydroxypregn-3,20-dione
• NSC9705
• 4-Pregnene-11-beta,21-diol-3,20-dione
• Pregn-4-ene-3,20-dione, 11beta,21-dihydroxy-
• Pregn-4-ene-3,20-dione, 11-beta,21-dihydroxy-
• (11-beta)-11,21-Dihydroxypregn-4-ene-3,20-dione
• MLS000028536
• CHEMBL110739
• 11.beta.,21-Dihydroxyprogesterone
• NCGC00022472-05
• SMR000058318
• 4-Pregnene-11.beta.,21-diol-3,20-dione
• Corticosterone 100 microg/mL in Acetonitrile
• (8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
• (11.beta.)-11,21-Dihydroxypregn-4-ene-3,20-dione
• 11,12-Dihydroxyprogesterone
• CCRIS 6753
• 11-beta,21-Dihydroxyprogesterone
• Compound B nach Kendall
• SR-01000075748
• NSC 9705
• EINECS 200-019-6
• Substanz H nach Reichstein
• BRN 2339601
• Cortico
• UNII-W980KJ009P
• Compd B
• CAS-50-22-6
• Prestwick_672
• Pregn-4-ene-3,20-dione, 11,21-dihydroxy-, (11b)-
• 21-dihydroxyprogesterone
• (11-BETA)-11,21-DIHYDROXY-PREGN-4-ENE-3,20-DIONE
• Opera_ID_1519
• Prestwick0_000432
• Prestwick1_000432
• Prestwick2_000432
• Prestwick3_000432
• Corticosterone (Standard)
• Corticosterone, >=92%
• 11-.beta.,20-dione
• bmse000669
• Epitope ID:152207
• CORTICOSTERONE [MI]
• BIDD:PXR0063
• Lopac0_000220
• SCHEMBL22612
• BSPBio_000444
• 4-Pregnene-11 Corticosteron
• MLS001074095
• MLS001424305
• Pregn-4-ene-3,20-dione, 11,21-dihydroxy-, (11.beta.)-
• BIDD:ER0495
• SPBio_002383
• BPBio1_000490
• GTPL2869
• orb1310140
• orb3025742
• HY-B1618R
• Corticosterone, BRN 2339601
• MSK8513
• 4-Pregnene-11.beta.,20-dione
• HMS1569G06
• HMS2052G21
• HMS2090A08
• HMS2096G06
• HMS2231F16
• HMS3260L21
• HMS3713G06
• HMS3885H22
• (8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
• Corticosterone, 1mg/ml in Methanol
• HY-B1618
• Tox21_110879
• Tox21_201366
• Tox21_303642
• Tox21_500220
• BDBM50170653
• CMC_13412
• EBC-85062
• HB2808
• HSCI1_000383
• LMST02030186
• MSK8513-100A
• s4752
• STL564760
• Corticosterone, >=98.5% (HPLC)
• AKOS016008541
• MSK8513-1000A
• Tox21_110879_1
• 11-b,21-Dihydroxypregn-3,20-dione
• CCG-101146
• CS-5105
• DB04652
• FC20555
• LP00220
• NC00396
• SDCCGSBI-0050208.P002
• SMP1_000079
• NCGC00022472-06
• NCGC00022472-07
• NCGC00022472-08
• NCGC00022472-10
• NCGC00022472-17
• NCGC00091029-01
• NCGC00256539-01
• NCGC00258918-01
• NCGC00260905-01
• 11|A
• AS-75743
• DA-52062
• SY075891
• 11,21-Dihydroxypregn-4-ene-3,20-dione
• 11-.beta.,21-Dihydroxypregn-3,20-dione
• 11b,21-Dihydroxy-4-pregnene-3,20-dione
• Pregn-4-ene-3, 11.beta.,21-dihydroxy-
• 4-Pregnen-11.beta.,21-diol-3,20-dione
• EU-0100220
• NS00000569
• C 2505
• C02140
• D94656
• Preg-4-ene-3,20-dione,11-b,21-dihydroxy-
• 11.beta.,21-dihydroxypregn-4-ene-3,20-dione
• Corticosterone Solution in Acetonitrile, 100ug/mL
• Corticosterone, VETRANAL(TM), analytical standard
• F235820
• Q422543
• SR-01000000082
• (11|_)-11,21-Dihydroxypregn-4-ene-3,20-dione
• Corticosterone Solution in Acetonitrile, 1000ug/mL
• Pregn-4-ene-3,20-dione, 11.beta.,21-dihydroxy-
• SR-01000000082-3
• SR-01000075748-1
• SR-01000075748-4
• WLN: L E5 B666 OV MUTJ A1 CQ E1 FV1Q
• BRD-K73589401-001-04-6
• BRD-K73589401-001-23-6
• Pregn-4-ene-3, 11,21-dihydroxy-, (11.beta.)-
• (9beta,11alpha)-11,21-dihydroxypregn-4-ene-3,20-dione
• 11,21-Dihydroxypregn-4-ene-3,20-dione, (11.beta.)- #
• 4793EB71-D789-498E-B641-C5C1C377B9FF
• 17-Deoxycortisol;11,21-Dihydroxyprogesterone;Kendall's compound B
• Pregn-4-ene-3,20-dione, 11,21-dihydroxy-, (11-beta)- (9CI)
• Kendall's Compound B; 4-Pregnene-11beta,21-diol-3,20-dione; Reichstein's Substance H
• (11b)-11,21-Dihydroxy-pregn-4-ene-3,20-dione;11,21-Dihydroxyprogesterone;17-Deoxycortisol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.6368	63.68%
Blood Brain Barrier	-	0.7763	77.63%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8517	85.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8923	89.23%
OATP1B3 inhibitior	+	0.9783	97.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.7024	70.24%
BSEP inhibitior	+	0.8635	86.35%
P-glycoprotein inhibitior	-	0.7908	79.08%
P-glycoprotein substrate	+	0.5085	50.85%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	-	0.8246	82.46%
CYP2C9 inhibition	-	0.9211	92.11%
CYP2C19 inhibition	-	0.9593	95.93%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9255	92.55%
CYP2C8 inhibition	-	0.7916	79.16%
CYP inhibitory promiscuity	-	0.8716	87.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6700	67.00%
Eye corrosion	-	0.9937	99.37%
Eye irritation	-	0.9740	97.40%
Skin irritation	+	0.6995	69.95%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.8648	86.48%
Human Ether-a-go-go-Related Gene inhibition	-	0.5928	59.28%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9123	91.23%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8212	82.12%
Acute Oral Toxicity (c)	III	0.7782	77.82%
Estrogen receptor binding	+	0.9177	91.77%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.7511	75.11%
Glucocorticoid receptor binding	+	0.9268	92.68%
Aromatase binding	+	0.8817	88.17%
PPAR gamma	-	0.8484	84.84%
Honey bee toxicity	-	0.8445	84.45%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9816	98.16%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	63.1 nM; 63.1 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1994	P08235	Mineralocorticoid receptor	0.5 nM	Kd	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	20 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	446.7 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	891.3 nM	Potency	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	457.09 nM	Kd	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.79%	91.11%
CHEMBL1871	P10275	Androgen Receptor	92.48%	96.43%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	91.41%	94.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.52%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	90.46%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.76%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.36%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.23%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	82.90%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.72%	93.04%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.48%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.14%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.59%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.49%	89.00%

Plants that contains it

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Cross-Links

• PubChem: 5753
• LOTUS: LTS0184473
• wikiData: Q422543