Dehydroepiandrosterone

Details

• Internal ID: 757879b4-1994-474d-a092-633e03e403b6
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Androstane steroids > Androgens and derivatives
• IUPAC Name: (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• InChI: InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
• InChI Key: FMGSKLZLMKYGDP-USOAJAOKSA-N
• Popularity: 21,160 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₂
• Molecular Weight: 288.40 g/mol
• Exact Mass: 288.208930132 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.88
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• DHEA
• PRASTERONE
• 53-43-0
• Dehydroisoandrosterone
• Androstenolone
• trans-Dehydroandrosterone
• Psicosterone
• Diandrone
• Diandron
• 3beta-hydroxyandrost-5-en-17-one
• Prestara
• 17-Hormoforin
• 17-Chetovis
• Andrestenol
• Intrarosa
• 5-Dehydroepiandrosterone
• Siscelar plus
• 3-beta-Hydroxy-5-androsten-17-one
• Dehydro-epi-androsterone
• 5,6-Didehydroisoandrosterone
• Prasterona
• Prasteronum
• Vaginorm
• (+)-Dehydroisoandrosterone
• 5,6-Dehydroisoandrosterone
• Caswell No. 051F
• dehydroepiandrosterone (dhea)
• Epiandrosterone, 5-dehydro-
• 5,6-Dehydroisoandrostorone
• Biolaif
• CCRIS 3277
• 3beta-hydroxy-5-androsten-17-one
• (3-beta)-3-Hydroxyandrost-5-en-17-one
• EM-760
• GL 701
• Astenile
• Deandros
• 5-Androsten-3beta-ol-17-one
• EPA Pesticide Chemical Code 126510
• Androst-5-en-17-one, 3-hydroxy-, (3beta)-
• Prasteronum [INN-Latin]
• Prasterona [INN-Spanish]
• DEHYDROISOANDOSTERONE
• NSC 9896
• NSC-9896
• EINECS 200-175-5
• UNII-459AG36T1B
• BRN 2058110
• Androst-5-en-17-one, 3-beta-hydroxy-
• DTXSID4020379
• CHEBI:28689
• dehydroepiandrostenedione
• NSC9896
• 459AG36T1B
• 3-beta-hydroxyandrost-5-en-17-one
• Androst-5-en-17-one, 3-hydroxy-, (3.beta.)-
• Androst-5-en-17-one, 3beta-hydroxy-
• (3beta)-3-hydroxyandrost-5-en-17-one
• CHEMBL90593
• DTXCID40379
• D5-Androsten-3beta-ol-17-one
• Androst-5-ene-3beta-ol-17-one
• EC 200-175-5
• Androst-5-en-17-one, 3-hydroxy-, (3-beta)-
• 4-08-00-00994 (Beilstein Handbook Reference)
• 3beta-Hydroxy-D5-androsten-17-one
• (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• Prasteronum (INN-Latin)
• Prasterona (INN-Spanish)
• PRASTERONE (MART.)
• PRASTERONE [MART.]
• (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one
• AND
• Prasterone [INN]
• Fidelin
• CAS-53-43-0
• SMR000059075
• Androst-5-en-17-one, 3.beta.-hydroxy-
• SR-01000075815
• Prasterone [USAN:INN]
• 5-Androsten-3.beta.-ol-17-one
• Anastar
• Inflabloc
• Aslera
• Fidelin T
• Androst-5-en-17-one, 3-hydroxy-, (3b)-
• DHEA; Prasterone
• GL701
• NCGC00093802-04
• NCGC00093802-06
• dehydroepiandosterone
• Biolaif (TN)
• 5 Androsten 3 beta hydroxy 17 one
• 5-Androsten-3-beta-hydroxy-17-one
• 5-dehydro-Epiandrosterone
• Prasterone (USAN/INN)
• trans-de-hydroandrosterone
• PRASTERONE [INCI]
• PRASTERONE [USAN]
• bmse000665
• Androsten-3beta-ol-17-one
• PRASTERONE [WHO-DD]
• BIDD:PXR0080
• Lopac0_000368
• SCHEMBL24156
• MLS001066350
• MLS001333231
• MLS001333232
• MLS001424274
• 5-Androsten-3B-ol-17-one
• D5-Androsten-3b-ol-17-one
• GTPL2370
• Androst-5-ene-3b-ol-17-one
• PRASTERONE [ORANGE BOOK]
• 3b-Hydroxyandrost-5-en-17-one
• 5-Androsten-3-beta-ol-17-one
• BCPE00002
• A14AA07
• G03XX01
• 3b-Hydroxy-D5-androsten-17-one
• 3beta-Hyroxyandrost-5-en-17-one
• BCPP000260
• DEHYDROEPIANDROSTERONE [MI]
• EL-10
• HMS2052P11
• HMS2090C04
• HMS2232K11
• IM 28
• trans-Dehydroandrosterone, >=99%
• 3-beta-hydroxy-5-androsten-17-on
• AMY25708
• BCP02453
• IPL-1001
• 3beta-hydroxy-androst-5-en-17-one
• 3beta-Hydroxyandrost-5-ene-17-one
• Tox21_111222
• Tox21_201996
• Tox21_302761
• BDBM50223368
• CMC_13435
• Delta5-androsten-3-beta-ol-17-one
• DL-373
• GL-701
• LMST02020021
• PB-007
• s2604
• DEHYDROEPIANDROSTERONE [VANDF]
• 3.beta.-Hydroxyandrost-5-en-17-one
• 5-Androsten-3beta-ol-17-one; DHEA
• AKOS007930299
• AKOS015951378
• Tox21_111222_1
• BCP9000602
• CCG-101190
• CS-1667
• DB01708
• FD12003
• GS-0906
• IP-1001
• NC00440
• SH-K-04828
• NCGC00093802-09
• NCGC00256412-01
• NCGC00259545-01
• (1S,5S,11S,15S,2R,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0<2,7>.0<11,15> ]heptadec-7-en-14-one
• (3beta)-3-Hydroxyandrost-5-ene-17-one
• AC-28716
• HY-14650
• NCI60_042215
• Prasterone (DHEA; Dehydroepiandrosterone)
• (3beta)-3-hydroxy-Androst-5-en-17-one
• D0044
• EU-0100368
• Androst-5-en-17-one, 3beta-hydroxy- (8CI)
• C01227
• D 4000
• D-0340
• D08409
• (3alpha,8alpha)-3-hydroxyandrost-5-en-17-one
• AB00375810-06
• AB00375810_09
• Dehydroepiandrosterone (DHEA), 1mg/ml in Methanol
• Q408376
• SR-01000075815-1
• SR-01000075815-4
• BRD-K41256143-001-12-7
• (3beta,16alpha)-3,16-dihydroxy-androst-5-en-17-one
• Androst-5-en-17-one, 3-hydroxy-, (3beta)- (9CI)
• 1A9D2040-240C-427D-ADE4-0CB700B785CB
• Prasterone (DHEA; Dehydroepiandrosterone) 1.0 mg/ml in Acetonitrile
• (1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
• (3S,8R,10R,13S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one
• 105597-37-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8234	82.34%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7019	70.19%
OATP2B1 inhibitior	-	0.8667	86.67%
OATP1B1 inhibitior	+	0.9738	97.38%
OATP1B3 inhibitior	+	0.9847	98.47%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6401	64.01%
BSEP inhibitior	-	0.5981	59.81%
P-glycoprotein inhibitior	-	0.7391	73.91%
P-glycoprotein substrate	-	0.6331	63.31%
CYP3A4 substrate	+	0.6812	68.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7781	77.81%
CYP3A4 inhibition	-	0.8399	83.99%
CYP2C9 inhibition	-	0.9672	96.72%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.9313	93.13%
CYP2C8 inhibition	+	0.4705	47.05%
CYP inhibitory promiscuity	-	0.9013	90.13%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Warning	0.5238	52.38%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9615	96.15%
Skin irritation	+	0.6046	60.46%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6636	66.36%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.9400	94.00%
skin sensitisation	+	0.5585	55.85%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6544	65.44%
Acute Oral Toxicity (c)	IV	0.6180	61.80%
Estrogen receptor binding	+	0.8286	82.86%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.5344	53.44%
PPAR gamma	-	0.7693	76.93%
Honey bee toxicity	-	0.8685	86.85%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9830	98.30%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3305	P04278	Testis-specific androgen-binding protein	14.45 nM	Kd	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	158.5 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	94.92%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.91%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.82%	100.00%
CHEMBL2581	P07339	Cathepsin D	90.15%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.97%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.61%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.59%	93.04%
CHEMBL1937	Q92769	Histone deacetylase 2	85.73%	94.75%
CHEMBL1871	P10275	Androgen Receptor	85.67%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.47%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.10%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.06%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	81.24%	95.93%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5881
• LOTUS: LTS0146846
• wikiData: Q408376