Dehydroepiandrosterone sulfate

Details

• Internal ID: b4c9280d-eaf1-4b2f-a02d-934d876df601
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Sulfated steroids
• IUPAC Name: [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
• SMILES (Canonical): CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(C4)OS(=O)(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C
• InChI: InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
• InChI Key: CZWCKYRVOZZJNM-USOAJAOKSA-N
• Popularity: 4,262 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₅S
• Molecular Weight: 368.50 g/mol
• Exact Mass: 368.16574516 g/mol
• Topological Polar Surface Area (TPSA): 89.10 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• DEHYDROEPIANDROSTERONE SULFATE
• DHEA sulfate
• 651-48-9
• Dehydroisoandrosterone sulfate
• Dehydroepiandrosterone sulphate
• DHEAS
• Dehydroandrosterone sulfate
• Dehydroepiandrosterone 3-sulfate
• Dehydroepiandrosterone monosulfate
• 3-O-Sulfodehydroepiandrosterone
• DHEA-S
• Dehydroisoandrosterone-3-sulfate
• Prasterone sulphate
• 17-Ketoandrost-5-en-3beta-yl sulfate
• 3beta-Hydroxyandrost-5-en-17-one 3-sulfate
• Androst-5-en-17-on-3beta-yl sulfuric acid
• CCRIS 6746
• DHEA sulphate
• (3-beta)-3-(Sulfooxy)androst-5-en-17-one
• Mylis
• CHEBI:16814
• 17-oxoandrost-5-en-3beta-yl hydrogen sulfate
• 57B09Q7FJR
• CHEMBL259898
• 651-48-9 (free acid)
• 17-oxoandrost-5-en-3beta-yl hydrogen sulphate
• Androst-5-en-17-one, 3-(sulfooxy)-, (3beta)-
• Androst-5-en-17-one, 3-(sulfooxy)-, (3.beta.)-
• [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
• 10,13-DIMETHYL-17-OXO-3-SULFOOXY-1,2,3,4,7,8,9,11,12,14,15,16-DODECAHYDROCYCLOPENTA[A]PHENANTHRENE
• Prasterone-3-sulfate
• (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl hydrogen sulfate
• NSC72822
• Formylisoglutamic acid
• 5-Androsten-3beta-sulfate-17-one
• 1099-87-2
• 3-beta-hydroxyandrost-5-en-17-one 3-sulfate
• dehydroepiandrosterone-sulfate
• UNII-57B09Q7FJR
• Inflarest
• 3beta-Hydroxyandrost-5-en-17-one-3-sulfate
• Androst-5-en-17-one, 3-(sulfooxy)-, (3b)-
• 17-Oxoandrost-5-en-3-yl hydrogen sulfate
• GENAFLOW
• Prasterone-3-sulphate
• Mylis (*Sodium Salt*)
• Teloin (*Sodium salt*)
• Epitope ID:150912
• Lopac0_000379
• SCHEMBL27640
• Dehydroisoandrosterone sulphate
• Androst-5-en-17-one, 3-(sulfooxy)-, (3-beta)-
• PRASTERONE SULFURIC ACID
• KB60
• Dehydroepiandrosterone-3-sulfate
• Androst-5-en-17-one, 3-beta-hydroxy-, hydrogen sulfate
• dehydroepiandrosterone-3-sulphate
• DTXSID8040228
• Dehydroepiandrosterone 3-sulphate
• Androst-5-en-17-one, 3.beta.-hydroxy-, hydrogen sulfate
• CZWCKYRVOZZJNM-USOAJAOKSA-N
• PRASTERONE SULFATE [MART.]
• Dehydroepiandrosterone 3beta-sulfate
• PRASTERONE SULFATE [WHO-DD]
• 3beta-Sulfooxy-5-androsten-17-one
• 5-Androsten-3-beta-sulfate-17-one
• BDBM50375559
• CMC_13438
• LMST05020010
• PB-005
• AKOS027320789
• Androst-5-en-17-on-3beta-yl sulfate
• DB05804
• Androst-5-en-17-one-3beta-yl sulfate
• Androst-5-ene-17-one-3beta-yl-sulfate
• MS-25917
• 3b-hydroxyandrost-5-en-17-one 3-sulfate
• 3beta-Hydroxy-5-androsten-17-one sulfate
• DEHYDROEPIANDROSTERONE SULFATE [MI]
• 17-Oxoandrost-5-en-3-yl hydrogen sulphate
• 17-oxoandrost-5-en-3b-yl hydrogen sulfate
• 3-b-hydroxyandrost-5-en-17-one 3-sulfate
• 3b-Hydroxyandrost-5-en-17-one 3-sulphate
• HY-113416
• 17-Oxoandrost-5-en-3b-yl hydrogen sulphate
• 3-b-Hydroxyandrost-5-en-17-one 3-sulphate
• 3beta-Hydroxy-5-androsten-17-one 3-sulfate
• CS-0059419
• (3beta)-3-(sulfooxy)-Androst-5-en-17-one
• 3beta-Hydroxy-5-androsten-17-one monosulfate
• 3beta-hydroxyandrost-5-en-17-one 3-sulphate
• 3-beta-Hydroxyandrost-5-en-17-one 3-sulphate
• C04555
• 3b-hydroxy-Androst-5-en-17-one hydrogen sulfate
• 3b-Hydroxy-Androst-5-en-17-one hydrogen sulphate
• (3beta)-17-oxoandrost-5-en-3-yl hydrogen sulfate
• 3beta-hydroxy-Androst-5-en-17-one hydrogen sulfate
• Q2505402
• 3beta-hydroxy-Androst-5-en-17-one hydrogen sulphate
• Dehydroepiandrosterone sulfate; DHEA sulfate; DHEA-S
• Androst-5-en-17-one, 3-(sulfooxy)-, (3beta)- (9CI)
• Androst-5-en-17-one, 3beta-hydroxy-, hydrogen sulfate (6CI,8CI)
• 17-oxo-8alpha,10alpha,13alpha,14beta-androst-5-en-3alpha-yl hydrogen sulfate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9776	97.76%
Caco-2	-	0.6284	62.84%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4844	48.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9451	94.51%
OATP1B3 inhibitior	+	0.8874	88.74%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7073	70.73%
BSEP inhibitior	+	0.7676	76.76%
P-glycoprotein inhibitior	-	0.5440	54.40%
P-glycoprotein substrate	-	0.8167	81.67%
CYP3A4 substrate	+	0.6646	66.46%
CYP2C9 substrate	-	0.8017	80.17%
CYP2D6 substrate	-	0.7970	79.70%
CYP3A4 inhibition	-	0.9481	94.81%
CYP2C9 inhibition	-	0.8400	84.00%
CYP2C19 inhibition	-	0.8117	81.17%
CYP2D6 inhibition	-	0.8820	88.20%
CYP1A2 inhibition	-	0.8203	82.03%
CYP2C8 inhibition	+	0.4857	48.57%
CYP inhibitory promiscuity	-	0.7575	75.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5600	56.00%
Carcinogenicity (trinary)	Non-required	0.5880	58.80%
Eye corrosion	-	0.9721	97.21%
Eye irritation	-	0.9705	97.05%
Skin irritation	-	0.7092	70.92%
Skin corrosion	-	0.7983	79.83%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5393	53.93%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.7240	72.40%
skin sensitisation	-	0.7699	76.99%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7177	71.77%
Acute Oral Toxicity (c)	III	0.6077	60.77%
Estrogen receptor binding	+	0.9089	90.89%
Androgen receptor binding	+	0.8042	80.42%
Thyroid receptor binding	+	0.7505	75.05%
Glucocorticoid receptor binding	+	0.9085	90.85%
Aromatase binding	+	0.5808	58.08%
PPAR gamma	+	0.5754	57.54%
Honey bee toxicity	-	0.7757	77.57%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1937	Q92769	Histone deacetylase 2	96.07%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.68%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.85%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.74%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.49%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.95%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.50%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	86.02%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.96%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.26%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.72%	94.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.51%	96.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.17%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.81%	93.04%
CHEMBL1871	P10275	Androgen Receptor	82.23%	96.43%
CHEMBL255	P29275	Adenosine A2b receptor	81.79%	98.59%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.61%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	81.31%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 12594
• LOTUS: LTS0143733
• wikiData: Q2505402