11-Deoxycortisol

Details

• Internal ID: 0833160c-0751-4a96-a4a0-b351c0d18811
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 21-hydroxysteroids
• IUPAC Name: (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• InChI: 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-OBQKJFGGSA-N
• Popularity: 2,615 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: 2.50
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CORTODOXONE
• 11-Deoxycortisol
• 152-58-9
• Reichstein's substance S
• 11-Desoxycortisol
• 11-Deoxyhydrocortisone
• Substance S
• 17,21-Dihydroxyprogesterone
• Cortisol, 11-deoxy-
• Reichstein S
• 11-Desoxyhydrocortisone
• 17alpha-Hydroxycortexone
• 17,21-Dihydroxypregn-4-ene-3,20-dione
• 11-Deoxy-17-hydroxycorticosterone
• 11-deoxycortisone
• 11-Dioxycortisol
• Reichstein's compound S
• 17-Hydroxy-11-deoxycorticosterone
• Pregn-4-ene-3,20-dione, 17,21-dihydroxy-
• SK&F 3050
• 11-Deoxy Cortisol
• 11-Desoxy-17-hydroxycorticosterone
• 4-Pregnene-17alpha,21-diol-3,20-dione
• NSC-18317
• Cortifen
• 17-alpha-Hydroxycortexone
• Cortodoxonum [INN-Latin]
• 17,21-Dihydroxy-4-pregnene-3,20-dione
• 17.alpha.-Hydroxycortexone
• Cortodoxona [INN-Spanish]
• SKF 3050
• 17,21-Dihydroxy-pregn-4-ene-3,20-dione
• Corticosterone, 11-deoxy-17-hydroxy-
• WDT5SLP0HQ
• Skf-3050
• MLS000069440
• DTXSID8045642
• CHEBI:28324
• SK&F-3050
• Cortodoxone (USAN)
• NCGC00021222-03
• SMR000059123
• 11-Desoxy-17.alpha.-hydroxycorticosterone
• 17alpha,21-Dihydroxy-4-pregnene-3,20-dione
• 4-Pregnene-17.alpha.,21-diol-3,20-dione
• CORTODOXONE [USAN]
• 17.alpha.,21-Dihydroxypregn-4-ene-3,20-dione
• 11-Desoxycortisone
• DTXCID6025642
• Cortodoxona
• Cortodoxonum
• 17,21-Dihydroxypregn-4-ene-3,20-dione (Reichstein's Substance S)
• 11 Deoxycortisol
• CAS-152-58-9
• UNII-WDT5SLP0HQ
• MFCD00003662
• Substance S, Reichstein's
• 17-hydroxydesoxycorticosterone
• Cortodoxone [USAN:INN:BAN]
• Hydrocortisone Imp. F (EP); 17,21-Dihydroxypregn-4-ene-3,20-dione; Reichstein's Substance S; 11-Deoxycortisol; Cortexolone; Hydrocortisone Impurity F
• EINECS 205-805-2
• BRN 2511358
• Opera_ID_1433
• CORTODOXONE [INN]
• 11-Deoxycortisol;cortexolone;Reichstein's substance S
• Lopac0_001040
• SCHEMBL42590
• 17a,21-dihydroxyprogesterone
• 4-08-00-02913 (Beilstein Handbook Reference)
• MLS001333071
• MLS001333072
• CHEMBL253144
• GTPL5100
• HMS2234L16
• HMS3263O21
• Reichstein's substance S, >=98%
• Tox21_110867
• Tox21_501040
• BDBM50423539
• CMC_13429
• LMST02030086
• s4775
• AKOS015969740
• Tox21_110867_1
• CCG-205117
• CS-5182
• LP01040
• SDCCGSBI-0051010.P002
• NCGC00021222-04
• NCGC00021222-05
• NCGC00021222-06
• NCGC00021222-07
• NCGC00261725-01
• (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• AS-56275
• HY-77839
• 11-Deoxycortisol, 1mg/ml in Acetonitrile
• 20-dione 17,21-Dihydroxypregn-4-ene-3
• 17.ALPHA.,21-DIHYDROXYPROGESTERONE
• EU-0101040
• C05488
• C72891
• D03595
• HYDROCORTISONE IMPURITY F [EP IMPURITY]
• R 0500
• 11-DESOXY-17-HYDROXYCORTICOSTERONE [MI]
• 17alpha,21-dihydroxy-pregna-4-ene-3,20-dione
• A936328
• SR-01000076100
• 4-PREGNEN-17.ALPHA.,21-DIOL-3,20-DIONE
• Q2064915
• SR-01000076100-1
• 17.ALPHA.,21-DIHYDROXY-4-PREGNEN-3,20-DIONE
• .DELTA.4-PREGNENE-17.ALPHA.,21-DIOL-3,20-DIONE
• 33BB233B-CC8F-413B-8901-3A73030BBA68
• 11-Deoxycortisol (17,21-Dihydroxypregn-4-ene-3,20-dione)
• 17-(1-keto-2-hydroxyethyl)-4-androsten-17alpha, 21-ol-3-one
• 17|A inverted exclamation mark,21-Dihydroxypregna-4-ene-3,20-dione
• 11-Deoxycortisol (17,21-Dihydroxypregn-4-ene-3,20-dione) 1.0 mg/ml in Methanol
• (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
• (8R,10R,13S,17R)-17-Hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
• (8R,9S,10R,13S,14S,17R)-17-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.8822	88.22%
Blood Brain Barrier	+	0.6793	67.93%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8362	83.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9415	94.15%
OATP1B3 inhibitior	+	0.9613	96.13%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6852	68.52%
BSEP inhibitior	+	0.9243	92.43%
P-glycoprotein inhibitior	-	0.5529	55.29%
P-glycoprotein substrate	-	0.7178	71.78%
CYP3A4 substrate	+	0.7580	75.80%
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	+	0.4840	48.40%
CYP inhibitory promiscuity	-	0.9095	90.95%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7360	73.60%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9796	97.96%
Skin irritation	+	0.6116	61.16%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.9251	92.51%
Human Ether-a-go-go-Related Gene inhibition	-	0.5121	51.21%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8922	89.22%
Acute Oral Toxicity (c)	III	0.7997	79.97%
Estrogen receptor binding	+	0.9041	90.41%
Androgen receptor binding	+	0.9159	91.59%
Thyroid receptor binding	+	0.7761	77.61%
Glucocorticoid receptor binding	+	0.9154	91.54%
Aromatase binding	+	0.8754	87.54%
PPAR gamma	-	0.7228	72.28%
Honey bee toxicity	-	0.8702	87.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9785	97.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	2.8 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	5 nM	Potency	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	36.31 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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.73%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	97.46%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.32%	91.11%
CHEMBL1871	P10275	Androgen Receptor	91.91%	96.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.72%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.78%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.43%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.31%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.04%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	81.68%	91.19%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.35%	94.78%
CHEMBL2581	P07339	Cathepsin D	81.17%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.84%	89.05%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 440707
• LOTUS: LTS0148049
• wikiData: Q2064915