Compound
17alpha-hydroxypregnenolone
A 21-carbon steroid that is converted from pregnenolone by steroid 17-alpha-hydroxylase. It is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids.
Structure
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- Class
- Organic compound
- Formula
- C21H32O3
- Mass
- 332.484 g/mol
- Charge
- 0
- InChIKey
- JERGUCIJOXJXHF-TVWVXWENSA-N
- SMILES
- [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1(O)C(C)=O
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
7 entities
7 entities reached.
0 reported hops7 assembled from the scaffold
- CYP17A1ProteinUNIPROT:P05093metabolized byInferred only168 paths28 endpoints
- HSD3B2ProteinUNIPROT:P26439substrate ofInferred only54 paths18 endpoints
- HSD3B1ProteinUNIPROT:P14060substrate ofInferred only54 paths18 endpoints
- STSProteinUNIPROT:P08842substrate ofInferred only42 paths14 endpoints
- ABCB1ProteinUNIPROT:P08183transported byInferred only21 paths20 endpoints
- CYP21A2ProteinUNIPROT:P08686metabolized byInferred only21 paths21 endpoints
- SULT2B1ProteinUNIPROT:O00204metabolized byInferred only5 paths5 endpoints
What the reference databases state
Statements
23 statements
23 statements · 2 reference databases · Subject: 17alpha-hydroxypregnenolone · Sources: Human-GEM, Rhea
- 17alpha-hydroxypregnenolone is converted to 17alpha-hydroxyprogesteroneCompoundHuman-GEM MAR07939Inferred only
- 17alpha-hydroxypregnenolone is converted to 17alpha-hydroxyprogesteroneCompoundHuman-GEM MAR07973Inferred only
- 17alpha-hydroxypregnenolone is converted to 17alpha,21-dihydroxypregnenoloneCompoundHuman-GEM MAR01948Inferred only
- pregnenolone is converted to 17alpha-hydroxypregnenoloneCompoundHuman-GEM MAR01944Inferred only
- pregnenolone is converted to 17alpha-hydroxypregnenoloneCompoundHuman-GEM MAR01945Inferred only
- 17alpha-hydroxypregnenolone is metabolised by CYP17A1ProteinHuman-GEM MAR01958Inferred only
- 17alpha-hydroxypregnenolone is metabolised by CYP17A1ProteinHuman-GEM MAR01960Inferred only
- 17alpha-hydroxypregnenolone is metabolised by CYP17A1ProteinRhea RHEA:50244Inferred only
- 17alpha-hydroxypregnenolone is metabolised by CYP17A1ProteinHuman-GEM MAR01959Inferred only
- 17alpha-hydroxypregnenolone is metabolised by CYP17A1ProteinHuman-GEM MAR02751Inferred only
- 17alpha-hydroxypregnenolone is metabolised by CYP17A1ProteinHuman-GEM MAR07936Inferred only
- 17alpha-hydroxypregnenolone is metabolised by CYP21A2ProteinHuman-GEM MAR01948Inferred only
Show the remaining 11
- 17alpha-hydroxypregnenolone is metabolised by SULT2B1ProteinHuman-GEM MAR01962Inferred only
- 17alpha-hydroxypregnenolone is a substrate of HSD3B1ProteinHuman-GEM MAR07973Inferred only
- 17alpha-hydroxypregnenolone is a substrate of HSD3B1ProteinHuman-GEM MAR07939Inferred only
- 17alpha-hydroxypregnenolone is a substrate of HSD3B1ProteinHuman-GEM MAR01982Inferred only
- 17alpha-hydroxypregnenolone is a substrate of HSD3B2ProteinHuman-GEM MAR07973Inferred only
- 17alpha-hydroxypregnenolone is a substrate of HSD3B2ProteinHuman-GEM MAR01982Inferred only
- 17alpha-hydroxypregnenolone is a substrate of HSD3B2ProteinHuman-GEM MAR07939Inferred only
- 17alpha-hydroxypregnenolone is a substrate of STSProteinHuman-GEM MAR02743Inferred only
- 17alpha-hydroxypregnenolone is a substrate of STSProteinHuman-GEM MAR02725Inferred only
- 17alpha-hydroxypregnenolone is a substrate of STSProteinHuman-GEM MAR02728Inferred only
- 17alpha-hydroxypregnenolone is transported by ABCB1ProteinHuman-GEM MAR11771Inferred only
Reactions
21 reactions
(20R)-17alpha,20-dihydroxycholesterol+4proton+2dioxygen+4reduced adrenodoxin17alpha-hydroxypregnenolone+3water+4-methylpentanal+4MAM02663c
Catalysed by CYP11A1
Reaction pageLeft to rightBalance undeterminableEC 1.14.15.6cytosol
Human-GEM MAR01934CC BY 4.0Reference data
proton+NADPH(4-)+dioxygen+pregnenolone17alpha-hydroxypregnenolone+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.14.19cytosol
Human-GEM MAR01944CC BY 4.0Reference data
proton+NADPH(4-)+dioxygen+pregnenolone17alpha-hydroxypregnenolone+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.14.19endoplasmic reticulum
Human-GEM MAR01945CC BY 4.0Reference data
17alpha-hydroxypregnenolone+proton+NADPH(4-)+dioxygen17alpha,21-dihydroxypregnenolone+water+NADP(3-)
Catalysed by CYP21A2
Reaction pageLeft to rightBalancedEC 1.14.14.16cytosol
Human-GEM MAR01948CC BY 4.0Reference data
17alpha-hydroxypregnenolone+2proton+2NADPH(4-)+dioxygenacetaldehyde+3beta-hydroxyandrost-5-en-17-one+2water+2NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.14.32cytosol
Human-GEM MAR01958CC BY 4.0Reference data
17alpha-hydroxypregnenolone+NADPH(4-)+dioxygenacetate+3beta-hydroxyandrost-5-en-17-one+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.99.-cytosol
Human-GEM MAR01959CC BY 4.0Reference data
17alpha-hydroxypregnenolone+NADPH(4-)+dioxygenacetate+3beta-hydroxyandrost-5-en-17-one+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageReversibleBalancedEC 1.14.99.-endoplasmic reticulum
Human-GEM MAR01960CC BY 4.0Reference data
17alpha-hydroxypregnenolone+3'-phospho-5'-adenylyl sulfateMAM00407c+proton+adenosine 3',5'-bismonophosphate
Catalysed by SULT2B1
Reaction pageLeft to rightBalancedEC 2.8.2.2cytosol
Human-GEM MAR01962CC BY 4.0Reference data
MAM00407c+water17alpha-hydroxypregnenolone+proton+sulfate
Catalysed by STS
Reaction pageLeft to rightBalancedEC 3.1.6.2cytosol
Human-GEM MAR01963CC BY 4.0Reference data
17alpha-hydroxypregnenolone+NAD(+)proton+NADH(2-)+MAM02761c
Reaction pageLeft to rightBalancedEC 1.1.1.145cytosol
Human-GEM MAR01982CC BY 4.0Reference data
MAM00407g+water17alpha-hydroxypregnenolone+proton+sulfate
Catalysed by STS
Reaction pageReversibleBalancedEC 3.1.6.2Golgi apparatus
Human-GEM MAR02725CC BY 4.0Reference data
MAM00407l+water17alpha-hydroxypregnenolone+proton+sulfate
Catalysed by STS
Reaction pageReversibleBalancedEC 3.1.6.2lysosome
Human-GEM MAR02728CC BY 4.0Reference data
Where it reaches
3 systems, 6 regions, 11 tissues, 11 transporter routes — routes, not measurements: transporters known to carry 17alpha-hydroxypregnenolone are expressed there, and no source reports it arriving.
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Other names
9 names
Resolves to: 17alpha-hydroxypregnenolone
- Also called
- (3beta)-3,17-dihydroxypregn-5-en-20-one(3β)-3,17-dihydroxypregn-5-en-20-one17-hydroxypregnenolone3beta,17alpha-dihydroxypregn-5-en-20-one5-pregnen-3beta,17alpha-diol-20-one5-pregnen-3β,17α-diol-20-oneST 21:2;O3
- Systematic name
- 3beta,17-dihydroxypregn-5-en-20-one3β,17-dihydroxypregn-5-en-20-one