Desoxycortone

Details

• Internal ID: 4351ed35-20fc-44e0-90cc-5cfa9a26be51
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 21-hydroxysteroids
• IUPAC Name: (8S,9S,10R,13S,14S,17S)-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): CC12CCC3C(C1CCC2C(=O)CO)CCC4=CC(=O)CCC34C
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CCC4=CC(=O)CC[C@]34C
• InChI: InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1
• InChI Key: ZESRJSPZRDMNHY-YFWFAHHUSA-N
• Popularity: 9,457 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.21949481 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 11-Deoxycorticosterone
• desoxycorticosterone
• Deoxycorticosterone
• 21-Hydroxyprogesterone
• 64-85-7
• Cortexone
• Deoxycortone
• Reichstein's substance Q
• 11-Desoxycorticosterone
• 4-Pregnen-21-ol-3,20-dione
• Desossicortone
• Kendall's desoxy compound B
• 11-Dehydroxycorticosterone
• Desoxycorticosteronum
• 21-Hydroxy-4-pregnene-3,20-dione
• Pregn-4-ene-3,20-dione, 21-hydroxy-
• Desoxicortona
• Desoxycortonum
• DTXSID0045254
• 40GP35YQ49
• 21-hydroxy-Pregn-4-ene-3,20-dione
• DTXCID8025254
• CHEBI:16973
• (8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• 11 Decorticosterone
• 11-Decorticosterone
• 21 Hydroxyprogesterone
• (8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-3-one
• 21 Hydroxy 4 pregnene 3,20 dione
• acAtate de dAsoxycortone
• RefChem:54955
• H02AA02
• (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadec-6-en-5-one
• 200-596-4
• 11-Deoxy Corticosterone
• Desoxicortonum
• Corticosterone, 11-deoxy-
• Progesterone, 21-hydroxy-
• DOC
• 1,2(3H)-Deoxycorticosterone
• NSC 11319
• MFCD00003661
• Deoxycorticosterone (Standard)
• MLS000028537
• MLS001076270
• 21-Hydroxy-3,20-dioxopregn-4-ene
• Desoxycortone (INN)
• SMR000058340
• DESOXYCORTONE [INN]
• Desossicortone [DCIT]
• [4-14C]-11-deoxycorticosterone
• Desoxycortonum [INN-Latin]
• Desoxicortona [INN-Spanish]
• 1CA
• 11-deoxy-Corticosterone
• EINECS 200-596-4
• Desoxycortone [INN:BAN]
• Deoxycortone;
• Ormosurrenol;
• UNII-40GP35YQ49
• Corthormon;
• Cortexone;
• Decortene;
• Ocriten;
• Desoxycorticosteron
• 'Reichstein Q'
• CAS-64-85-7
• NCGC00016292-01
• Deoxycorticosterone?
• 11-Dcortic
• Cortexon;Corticormon;
• DOCA (Salt/Mix)
• Opera_ID_581
• 21-hydroxy-Progesterone
• Prestwick0_000957
• Prestwick1_000957
• Prestwick2_000957
• Prestwick3_000957
• bmse000535
• SCHEMBL4065
• CHEMBL1498
• BSPBio_000954
• Kendall's desoxy compound B;
• DESOXYCORTONE [MART.]
• SPBio_003103
• DESOXYCORTONE [WHO-DD]
• BDBM8582
• BPBio1_001050
• GTPL2871
• orb1306701
• orb3141082
• DEOXYCORTICOSTERONE [MI]
• hydroxy-4-pregnene-3,20-dione
• MSK2205
• 4-pregnene-3,20-dione-21-ol
• HMS1570P16
• HMS2097P16
• HMS2235G07
• HMS3714P16
• D4-Pregnene-21-ol-3,20-dione
• DESOXYCORTICOSTERONE [VANDF]
• Tox21_110356
• Tox21_302402
• CMC_13409
• LMST02030087
• MSK2205-100A
• Delta4-Pregnene-21-ol-3,20-dione
• 21-Hydroxy-D4-pregnane-3,20-dione
• 21-Hydroxy-D4-pregnene-3,20-dione
• AKOS005111365
• MSK2205-1000A
• Tox21_110356_1
• CCG-220957
• EBC-384095
• FD21043
• HY-113414R
• 21-Hydroxypregn-4-ene-3,20-dione #
• NCGC00021304-03
• NCGC00021304-05
• NCGC00256184-01
• (1S,3aS,3bS,9aR,9bS,11aS)-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
• 21-Hydroxy-Delta4-pregnane-3,20-dione
• 21-Hydroxy-Delta4-pregnene-3,20-dione
• 21-Hydroxyprogesterone, >=97% (HPLC)
• AS-77189
• SY272200
• HY-113414
• AB00490029
• CS-0059402
• Deoxycorticosterone; 11-Deoxy Corticosterone
• NS00005226
• (14beta)-21-hydroxypregn-4-ene-3,20-dione
• C03205
• D07792
• G60883
• T20302
• F866023
• Q948846
• SR-01000003106
• 21-HYDROXY-.DELTA.4-PREGNENE-3,20-DIONE
• SR-01000003106-2
• BRD-K98521173-001-03-8
• BRD-K98521173-001-19-4
• Desoxycorticosterone Solution in Acetonitrile, 1000ug/mL
• Desoxycorticosterone Solution in Acetonitrile, 100ug/mL
• BD5D7BC9-0CD8-404E-9BA0-F670962012F8
• 4-PREGNEN-21-OL-3,20-DIONE; DOC; 21-HYDROXYPROGESTERONE
• (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• (8S,10R,13S,17S)-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
• (8S,9S,10R,13S,14S,17S)-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
• (8S,9S,10R,13S,14S,17S)-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.8394	83.94%
Blood Brain Barrier	+	0.5168	51.68%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8619	86.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8496	84.96%
OATP1B3 inhibitior	+	0.9764	97.64%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.7045	70.45%
BSEP inhibitior	+	0.9071	90.71%
P-glycoprotein inhibitior	+	0.6485	64.85%
P-glycoprotein substrate	-	0.8418	84.18%
CYP3A4 substrate	+	0.7885	78.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8859	88.59%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9123	91.23%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9087	90.87%
CYP inhibitory promiscuity	-	0.8070	80.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6032	60.32%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9736	97.36%
Skin irritation	+	0.5816	58.16%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	-	0.8948	89.48%
Human Ether-a-go-go-Related Gene inhibition	-	0.5125	51.25%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8612	86.12%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8997	89.97%
Acute Oral Toxicity (c)	III	0.7315	73.15%
Estrogen receptor binding	+	0.9066	90.66%
Androgen receptor binding	+	0.8957	89.57%
Thyroid receptor binding	+	0.8141	81.41%
Glucocorticoid receptor binding	+	0.9265	92.65%
Aromatase binding	+	0.8434	84.34%
PPAR gamma	-	0.7991	79.91%
Honey bee toxicity	-	0.8906	89.06%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9843	98.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	25.1 nM	Potency	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	41.69 nM	Kd	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	98.11%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	97.53%	100.00%
CHEMBL1871	P10275	Androgen Receptor	93.82%	96.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.78%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.15%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.85%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.49%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	85.31%	95.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.77%	93.04%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.53%	94.78%
CHEMBL340	P08684	Cytochrome P450 3A4	82.09%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.95%	95.89%

Plants that contains it

• Alstonia congensis
• Alstonia scholaris
• Amsonia tomentosa
• Aspidosperma quebracho-blanco
• Gelsemium elegans
• Kopsia singapurensis
• Picralima nitida
• Strychnos potatorum
• Tabernaemontana ciliata

Cross-Links

• PubChem: 6166
• LOTUS: LTS0005882
• wikiData: Q105233584