Compound
17beta-hydroxy-5alpha-androstan-3-one
A potent androgenic metabolite of testosterone. It is produced by the action of the enzyme 3-oxo-5-alpha-steroid 4-dehydrogenase.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C19H30O2
- Mass
- 290.447 g/mol
- Charge
- 0
- InChIKey
- NVKAWKQGWWIWPM-ABEVXSGRSA-N
- SMILES
- [H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@@H](O)CC[C@@]34[H])[C@@]1(C)CCC(=O)C2
- 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
- CYP3A4ProteinUNIPROT:P08684metabolized byInferred only106 paths53 endpoints
- AKR1C3ProteinUNIPROT:P42330substrate ofInferred only103 paths35 endpoints
- HSD3B1ProteinUNIPROT:P14060substrate ofInferred only90 paths18 endpoints
- AKR1C4ProteinUNIPROT:P17516substrate ofInferred only84 paths21 endpoints
- AKR1C1ProteinUNIPROT:Q04828substrate ofInferred only75 paths25 endpoints
- HSD17B10ProteinUNIPROT:Q99714substrate ofInferred only64 paths32 endpoints
- HSD3B2ProteinUNIPROT:P26439substrate ofInferred only54 paths18 endpoints
- STSProteinUNIPROT:P08842substrate ofInferred only42 paths14 endpoints
- AKR1C2ProteinUNIPROT:P52895substrate ofInferred only32 paths16 endpoints
- CYP19A1ProteinUNIPROT:P11511metabolized byInferred only26 paths26 endpoints
- UGT1A1ProteinUNIPROT:P22309metabolized byInferred only25 paths25 endpoints
- SULT2A1ProteinUNIPROT:Q06520metabolized byInferred only24 paths24 endpoints
Show the remaining 13
- UGT1A8ProteinUNIPROT:Q9HAW9metabolized byInferred only22 paths11 endpoints
- DHRS9ProteinUNIPROT:Q9BPW9substrate ofInferred only18 paths9 endpoints
- HSD17B7ProteinUNIPROT:P56937substrate ofInferred only17 paths17 endpoints
- RDH5ProteinUNIPROT:Q92781substrate ofInferred only16 paths16 endpoints
- UGT1A10ProteinUNIPROT:Q9HAW8metabolized byInferred only14 paths14 endpoints
- HSD17B2ProteinUNIPROT:P37059substrate ofInferred only12 paths12 endpoints
- UGT2B4ProteinUNIPROT:P06133metabolized byInferred only11 paths11 endpoints
- UGT2B15ProteinUNIPROT:P54855metabolized byInferred only10 paths10 endpoints
- UGT2B17ProteinUNIPROT:O75795metabolized byInferred only9 paths9 endpoints
- HSD17B6ProteinUNIPROT:O14756substrate ofInferred only8 paths4 endpoints
- UGT2B28ProteinUNIPROT:Q9BY64metabolized byInferred only8 paths8 endpoints
- RDH16ProteinUNIPROT:O75452substrate ofInferred only7 paths7 endpoints
- HSD17B8ProteinUNIPROT:Q92506substrate ofInferred only5 paths5 endpoints
What the reference databases state
Chemical structure
- 17beta-hydroxy-3,19-dioxo-5alpha-androstanone has the functional parent 17beta-hydroxy-5alpha-androstan-3-oneCompoundChEBI CHEBI:137032Inferred only
Statements
65 statements
65 statements · 2 reference databases · Subject: 17beta-hydroxy-5alpha-androstan-3-one · Sources: Human-GEM, Rhea
- 5alpha-androstan-3,17-dione is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundRhea RHEA:42120Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to 5alpha-androstan-3,17-dioneCompoundRhea RHEA:41992Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to 5alpha-androstane-3alpha,17beta-diolCompoundRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to 5alpha-androstane-3alpha,17beta-diolCompoundRhea RHEA:42116Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to 5alpha-androstane-3alpha,17beta-diolCompoundHuman-GEM MAR01978Inferred only
- 5alpha-androstane-3alpha,17beta-diol is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundHuman-GEM MAR01978Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to 5alpha-dihydrotestosterone 17-O-(beta-D-glucuronate)CompoundHuman-GEM MAR07987Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to 5alpha-dihydrotestosterone 17-O-(beta-D-glucuronate)CompoundRhea RHEA:53000Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to 5alpha-dihydrotestosterone sulfateCompoundHuman-GEM MAR07974Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to androst-5-en-3beta,17beta-diolCompoundHuman-GEM MAR03400Inferred only
- androst-5-en-3beta,17beta-diol is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundHuman-GEM MAR02024Inferred only
- androst-5-en-3beta,17beta-diol is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundHuman-GEM MAR03400Inferred only
Show the remaining 53
- 17beta-hydroxy-5alpha-androstan-3-one is converted to androst-5-en-3beta,17beta-diolCompoundHuman-GEM MAR02024Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is converted to androst-5-en-3beta,17beta-diolCompoundHuman-GEM MAR02022Inferred only
- androst-5-en-3beta,17beta-diol is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundHuman-GEM MAR02022Inferred only
- testosterone is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundHuman-GEM MAR01976Inferred only
- testosterone is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundHuman-GEM MAR01977Inferred only
- testosterone is converted to 17beta-hydroxy-5alpha-androstan-3-oneCompoundRhea RHEA:50820Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by CYP19A1ProteinRhea RHEA:53200Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by CYP3A4ProteinRhea RHEA:53212Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by CYP3A4ProteinRhea RHEA:53200Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by SULT2A1ProteinHuman-GEM MAR07974Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT1A1ProteinHuman-GEM MAR07987Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT1A10ProteinHuman-GEM MAR07987Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT1A8ProteinRhea RHEA:53000Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT1A8ProteinHuman-GEM MAR07987Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT2B15ProteinRhea RHEA:53000Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT2B17ProteinRhea RHEA:53000Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT2B28ProteinHuman-GEM MAR07987Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is metabolised by UGT2B4ProteinHuman-GEM MAR07987Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C1ProteinRhea RHEA:42116Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C1ProteinRhea RHEA:16297Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C1ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C2ProteinRhea RHEA:42116Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C2ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C3ProteinRhea RHEA:16297Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C3ProteinRhea RHEA:42116Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C3ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C4ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C4ProteinHuman-GEM MAR01978Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C4ProteinRhea RHEA:16297Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of AKR1C4ProteinRhea RHEA:42116Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of DHRS7ProteinRhea RHEA:42116Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of DHRS9ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of DHRS9ProteinRhea RHEA:41992Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD17B10ProteinRhea RHEA:41992Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD17B10ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD17B2ProteinRhea RHEA:41992Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD17B6ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD17B6ProteinRhea RHEA:42184Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD17B7ProteinRhea RHEA:16297Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD17B8ProteinRhea RHEA:41992Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B1ProteinRhea RHEA:16297Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B1ProteinHuman-GEM MAR02022Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B1ProteinHuman-GEM MAR02024Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B1ProteinHuman-GEM MAR03400Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B1ProteinRhea RHEA:42184Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B2ProteinHuman-GEM MAR03400Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B2ProteinHuman-GEM MAR02024Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of HSD3B2ProteinHuman-GEM MAR02022Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of RDH16ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of RDH5ProteinRhea RHEA:42004Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of STSProteinHuman-GEM MAR03601Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of STSProteinHuman-GEM MAR02025Inferred only
- 17beta-hydroxy-5alpha-androstan-3-one is a substrate of STSProteinHuman-GEM MAR03600Inferred only
Reactions
24 reactions
proton+NADPH(4-)+testosterone17beta-hydroxy-5alpha-androstan-3-one+NADP(3-)
Catalysed by SRD5A3 or SRD5A1 or SRD5A2
Reaction pageLeft to rightBalancedEC 1.3.1.22cytosol
Human-GEM MAR01976CC BY 4.0Reference data
proton+NADPH(4-)+testosterone17beta-hydroxy-5alpha-androstan-3-one+NADP(3-)
Catalysed by SRD5A3 or SRD5A1 or SRD5A2
Reaction pageLeft to rightBalancedEC 1.3.1.22endoplasmic reticulum
Human-GEM MAR01977CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+proton+NADPH(4-)5alpha-androstane-3alpha,17beta-diol+NADP(3-)
Catalysed by AKR1C4
Reaction pageReversibleBalancedEC 1.1.1.50cytosol
Human-GEM MAR01978CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+NADH(2-)androst-5-en-3beta,17beta-diol+proton+NAD(+)
Reaction pageReversibleUnbalancedEC 1.1.1.145cytosol
Human-GEM MAR02022CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+NADH(2-)androst-5-en-3beta,17beta-diol+proton+NAD(+)
Reaction pageReversibleUnbalancedEC 1.1.1.145endoplasmic reticulum
Human-GEM MAR02024CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+proton+sulfate5alpha-dihydrotestosterone sulfate+water
Catalysed by STS
Reaction pageReversibleBalancedEC 3.1.6.2cytosol
Human-GEM MAR02025CC BY 4.0Reference data
androst-5-en-3beta,17beta-diol+proton+NAD(+)17beta-hydroxy-5alpha-androstan-3-one+NADH(2-)
Reaction pageReversibleUnbalancedEC 1.1.1.145mitochondrial matrix
Human-GEM MAR03400CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+proton+sulfate5alpha-dihydrotestosterone sulfate+water
Catalysed by STS
Reaction pageReversibleBalancedEC 3.1.6.2lysosome
Human-GEM MAR03600CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+proton+sulfate5alpha-dihydrotestosterone sulfate+water
Catalysed by STS
Reaction pageReversibleBalancedEC 3.1.6.2endoplasmic reticulum
Human-GEM MAR03601CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+3'-phospho-5'-adenylyl sulfate5alpha-dihydrotestosterone sulfate+proton+adenosine 3',5'-bismonophosphate
Catalysed by SULT2A1
Reaction pageLeft to rightBalancedEC 2.8.2.14cytosol
Human-GEM MAR07974CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one+UDP-alpha-D-glucuronate5alpha-dihydrotestosterone 17-O-(beta-D-glucuronate)+UDP
Catalysed by UGT2B28 or UGT2B4 or UGT1A1 or UGT1A8 or UGT1A10
Reaction pageLeft to rightBalancedEC 2.4.1.17endoplasmic reticulum
Human-GEM MAR07987CC BY 4.0Reference data
17beta-hydroxy-5alpha-androstan-3-one17beta-hydroxy-5alpha-androstan-3-one
Reaction pageReversibleBalancedcytosol, endoplasmic reticulum
Human-GEM MAR07988CC BY 4.0Reference data
Other names
14 names
Resolves to: 17beta-hydroxy-5alpha-androstan-3-one
- Also called
- 17beta-hydroxy-androstan-3-one17beta-Hydroxyandrostan-3-one4,5alpha-dihydrotestosterone4,5α-dihydrotestosterone5alpha-DHT5alpha-dihydrotesosterone5alpha-Dihydrotestosterone5α-DHTAndrostanoloneDHTDIHYDROTESTOSTERONEST 19:1;O2Stanolone
- Systematic name
- 17β-hydroxy-5α-androstan-3-one