Compound
androst-4-ene-3,17-dione
A delta-4 C19 steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C19H26O2
- Mass
- 286.415 g/mol
- Charge
- 0
- InChIKey
- AEMFNILZOJDQLW-QAGGRKNESA-N
- SMILES
- [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=O)CC[C@@]21[H]
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
25 entities
25 entities reached.
0 reported hops25 assembled from the scaffold
- CYP19A1ProteinUNIPROT:P11511metabolized byInferred only104 paths26 endpoints
- AKR1C3ProteinUNIPROT:P42330substrate ofInferred only97 paths33 endpoints
- CYP17A1ProteinUNIPROT:P05093metabolized byInferred only56 paths28 endpoints
- CYP3A4ProteinUNIPROT:P08684metabolized byInferred only53 paths53 endpoints
- HSD17B3ProteinUNIPROT:P37058substrate ofInferred only51 paths17 endpoints
- HSD17B1ProteinUNIPROT:P14061substrate ofInferred only45 paths15 endpoints
- SRD5A3ProteinUNIPROT:Q9H8P0substrate ofInferred only36 paths18 endpoints
- HSD17B7ProteinUNIPROT:P56937substrate ofInferred only34 paths17 endpoints
- AKR1D1ProteinUNIPROT:P51857substrate ofInferred only30 paths15 endpoints
- AKR1C1ProteinUNIPROT:Q04828substrate ofInferred only25 paths25 endpoints
- CYP2D6ProteinUNIPROT:P10635metabolized byInferred only24 paths24 endpoints
- HSD17B2ProteinUNIPROT:P37059substrate ofInferred only24 paths12 endpoints
Show the remaining 13
- SRD5A1ProteinUNIPROT:P18405substrate ofInferred only22 paths11 endpoints
- ABCB1ProteinUNIPROT:P08183transported byInferred only21 paths20 endpoints
- CYP11B1ProteinUNIPROT:P15538metabolized byInferred only21 paths21 endpoints
- AKR1C4ProteinUNIPROT:P17516substrate ofInferred only21 paths21 endpoints
- CYP3A5ProteinUNIPROT:P20815metabolized byInferred only18 paths18 endpoints
- AKR1C2ProteinUNIPROT:P52895substrate ofInferred only16 paths16 endpoints
- HSD17B12ProteinUNIPROT:Q53GQ0substrate ofInferred only13 paths13 endpoints
- SRD5A2ProteinUNIPROT:P31213substrate ofInferred only13 paths13 endpoints
- HSD17B6ProteinUNIPROT:O14756substrate ofInferred only12 paths4 endpoints
- HSD17B8ProteinUNIPROT:Q92506substrate ofInferred only10 paths5 endpoints
- testosteroneCompoundCHEBI:17347converted toInferred only8 paths2 endpoints
- HSD17B11ProteinUNIPROT:Q8NBQ5substrate ofInferred only8 paths5 endpoints
- AKR1B15ProteinUNIPROT:C9JRZ8substrate ofInferred only5 paths5 endpoints
What the reference databases state
Regulatory determinations
LiverTox likelihood score ALiverTox
LiverTox Likelihood Score A — well known, well described and well reported to cause liver injury. Chapter: "Androstenedione". Source: LiverTox Master List (NBK571102).
The document·Public Domain (NLM/NIH)·Transcribed, not assessed
Chemical structure
- 19-oxo-androst-4-ene-3,17-dione has the functional parent androst-4-ene-3,17-dioneCompoundChEBI CHEBI:799Inferred only
- 6beta-hydroxyandrost-4-ene-3,17-dione has the functional parent androst-4-ene-3,17-dioneCompoundChEBI CHEBI:87571Inferred only
Statements
61 statements
61 statements · 2 reference databases · Subject: androst-4-ene-3,17-dione · Sources: Human-GEM, Rhea
- androst-4-ene-3,17-dione is converted to 19-hydroxyandrost-4-ene-3,17-dioneCompoundHuman-GEM MAR02032Inferred only
- 3beta-hydroxyandrost-5-en-17-one is converted to androst-4-ene-3,17-dioneCompoundHuman-GEM MAR07954Inferred only
- androst-4-ene-3,17-dione is converted to 5alpha-androstan-3,17-dioneCompoundHuman-GEM MAR02015Inferred only
- 5alpha-androstan-3,17-dione is converted to androst-4-ene-3,17-dioneCompoundHuman-GEM MAR02014Inferred only
- 5alpha-androstan-3,17-dione is converted to androst-4-ene-3,17-dioneCompoundHuman-GEM MAR02015Inferred only
- androst-4-ene-3,17-dione is converted to 5alpha-androstan-3,17-dioneCompoundHuman-GEM MAR02014Inferred only
- androst-4-ene-3,17-dione is converted to 5alpha-androstan-3,17-dioneCompoundRhea RHEA:50816Inferred only
- 5alpha-androstan-3,17-dione is converted to androst-4-ene-3,17-dioneCompoundRhea RHEA:50816Inferred only
- androst-4-ene-3,17-dione is converted to 5beta-androstane-3,17-dioneCompoundRhea RHEA:46656Inferred only
- androst-5-ene-3,17-dione is converted to androst-4-ene-3,17-dioneCompoundHuman-GEM MAR01971Inferred only
- androst-5-ene-3,17-dione is converted to androst-4-ene-3,17-dioneCompoundHuman-GEM MAR01970Inferred only
- androst-5-ene-3,17-dione is converted to androst-4-ene-3,17-dioneCompoundRhea RHEA:43936Inferred only
Show the remaining 49
- androst-4-ene-3,17-dione is converted to testosteroneCompoundHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is converted to testosteroneCompoundHuman-GEM MAR07955Inferred only
- androst-4-ene-3,17-dione is converted to testosteroneCompoundHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is converted to testosteroneCompoundRhea RHEA:14981Inferred only
- testosterone is converted to androst-4-ene-3,17-dioneCompoundRhea RHEA:14929Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP11B1ProteinRhea RHEA:84071Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP17A1ProteinRhea RHEA:53228Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP17A1ProteinHuman-GEM MAR01987Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP19A1ProteinHuman-GEM MAR02032Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP19A1ProteinRhea RHEA:38195Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP19A1ProteinHuman-GEM MAR07940Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP19A1ProteinRhea RHEA:38199Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP2D6ProteinHuman-GEM MAR09937Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP3A4ProteinRhea RHEA:47256Inferred only
- androst-4-ene-3,17-dione is metabolised by CYP3A5ProteinRhea RHEA:47256Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1B15ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1C1ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1C2ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1C3ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1C3ProteinHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1C3ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1C4ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1D1ProteinHuman-GEM MAR02014Inferred only
- androst-4-ene-3,17-dione is a substrate of AKR1D1ProteinRhea RHEA:46656Inferred only
- androst-4-ene-3,17-dione is a substrate of DHRS1ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B1ProteinHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B1ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B1ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B11ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B11ProteinHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B12ProteinHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B2ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B2ProteinHuman-GEM MAR07955Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B3ProteinHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B3ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B3ProteinRhea RHEA:14981Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B6ProteinHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B6ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B6ProteinHuman-GEM MAR07955Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B7ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B7ProteinHuman-GEM MAR01974Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B8ProteinHuman-GEM MAR01973Inferred only
- androst-4-ene-3,17-dione is a substrate of HSD17B8ProteinHuman-GEM MAR07955Inferred only
- androst-4-ene-3,17-dione is a substrate of SRD5A1ProteinRhea RHEA:50816Inferred only
- androst-4-ene-3,17-dione is a substrate of SRD5A1ProteinHuman-GEM MAR02015Inferred only
- androst-4-ene-3,17-dione is a substrate of SRD5A2ProteinHuman-GEM MAR02015Inferred only
- androst-4-ene-3,17-dione is a substrate of SRD5A3ProteinHuman-GEM MAR02015Inferred only
- androst-4-ene-3,17-dione is a substrate of SRD5A3ProteinRhea RHEA:50816Inferred only
- androst-4-ene-3,17-dione is transported by ABCB1ProteinHuman-GEM MAR11757Inferred only
Reactions
39 reactions
androst-5-ene-3,17-dione+proton+NAD(+)androst-4-ene-3,17-dione+NADH(2-)
Reaction pageLeft to rightUnbalancedEC 5.3.3.1cytosol
Human-GEM MAR01970CC BY 4.0Reference data
androst-5-ene-3,17-dione+proton+NAD(+)androst-4-ene-3,17-dione+NADH(2-)
Reaction pageLeft to rightUnbalancedEC 5.3.3.1endoplasmic reticulum
Human-GEM MAR01971CC BY 4.0Reference data
androst-4-ene-3,17-dione+proton+NADPH(4-)NADP(3-)+testosterone
Catalysed by HSD17B6 or HSD17B2 or HSD17B1 or HSD17B3 or HSD17B7 or AKR1C3 or HSD17B11 or HSD17B8
Reaction pageLeft to rightBalancedEC 1.1.1.62, 1.1.1.64cytosol
Human-GEM MAR01973CC BY 4.0Reference data
androst-4-ene-3,17-dione+proton+NADPH(4-)NADP(3-)+testosterone
Catalysed by HSD17B6 or HSD17B1 or HSD17B3 or HSD17B7 or HSD17B12 or AKR1C3 or HSD17B11
Reaction pageLeft to rightBalancedEC 1.1.1.62, 1.1.1.64endoplasmic reticulum
Human-GEM MAR01974CC BY 4.0Reference data
17alpha-hydroxyprogesterone+NADPH(4-)+dioxygenandrost-4-ene-3,17-dione+acetate+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.99.-cytosol
Human-GEM MAR01985CC BY 4.0Reference data
17alpha-hydroxyprogesterone+NADPH(4-)+dioxygenandrost-4-ene-3,17-dione+acetate+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageReversibleBalancedEC 1.14.99.-endoplasmic reticulum
Human-GEM MAR01987CC BY 4.0Reference data
androst-4-ene-3,17-dione+proton+NADPH(4-)5alpha-androstan-3,17-dione+NADP(3-)
Catalysed by AKR1D1
Reaction pageReversibleBalancedEC 1.3.1.3, 1.3.99.6cytosol
Human-GEM MAR02014CC BY 4.0Reference data
androst-4-ene-3,17-dione+proton+NADPH(4-)5alpha-androstan-3,17-dione+NADP(3-)
Catalysed by SRD5A3 or SRD5A1 or SRD5A2
Reaction pageReversibleBalancedEC 1.3.1.22endoplasmic reticulum
Human-GEM MAR02015CC BY 4.0Reference data
androst-4-ene-3,17-dione+2proton+dioxygen19-hydroxyandrost-4-ene-3,17-dione+water
Catalysed by CYP19A1
Reaction pageLeft to rightUnbalancedEC 1.14.14.1cytosol
Human-GEM MAR02032CC BY 4.0Reference data
17alpha-hydroxyprogesterone+NADPH(4-)+dioxygenandrost-4-ene-3,17-dione+acetate+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 2.4.1.17mitochondrial matrix
Human-GEM MAR02723CC BY 4.0Reference data
17alpha-hydroxyprogesterone+proton+NADPH(4-)+0.5dioxygenandrost-4-ene-3,17-dione+acetaldehyde+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.14.19endoplasmic reticulum
Human-GEM MAR07938CC BY 4.0Reference data
androst-4-ene-3,17-dione+NADPH(4-)+2dioxygenestrone+formic acid+2water+NADP(3-)
Catalysed by CYP19A1
Reaction pageLeft to rightBalancedEC 1.14.14.14endoplasmic reticulum
Human-GEM MAR07940CC BY 4.0Reference data
On the label
Labelled products
4 products
Source: NIH DSLD · Ingredient: androst-4-ene-3,17-dione · 4 products · Declared amount per serving: 5–100 mg (3 products)
3 labels state an amount1 does not
- Douglas LaboratoriesAndrostenedione-2525 mgper 1 Tablet(s)DSLD:10177
- Douglas LaboratoriesAndrostenedione-55 mgper 1 Tablet(s)DSLD:10176
- Douglas LaboratoriesMorphos Stack100 mgper 3 Capsule(s)DSLD:10321
- iForce NutritionAnti-Aromatase Reversitol Testosteroneamount not statedper 1 Capsule(s)DSLD:27893
Label record: NIH Office of Dietary Supplements · CC0
Where it reaches
3 systems, 6 regions, 11 tissues, 11 transporter routes — routes, not measurements: transporters known to carry androst-4-ene-3,17-dione are expressed there, and no source reports it arriving.
Loading the model…
Other names
8 names
Resolves to: androst-4-ene-3,17-dione
- Also called
- 4-ANDROSTENE-3-17-DIONE4-Androstene-3,17-dioneAndrostenedioneDelta(4)-androsten-3,17-dioneDelta(4)-androstene-3,17-dioneST 19:3;O2Δ4-androsten-3,17-dioneΔ4-androstene-3,17-dione