Compound
17alpha-hydroxyprogesterone
A metabolite of progesterone with a hydroxyl group at the 17-alpha position. It serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones.
Structure
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- Class
- Organic compound
- Formula
- C21H30O3
- Mass
- 330.468 g/mol
- Charge
- 0
- InChIKey
- DBPWSSGDRRHUNT-CEGNMAFCSA-N
- SMILES
- [H][C@@]12CCC3=CC(=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
6 entities
6 entities reached.
0 reported hops6 assembled from the scaffold
- CYP17A1ProteinUNIPROT:P05093metabolized byInferred only168 paths28 endpoints
- CYP21A2ProteinUNIPROT:P08686metabolized byInferred only63 paths21 endpoints
- AKR1C1ProteinUNIPROT:Q04828substrate ofInferred only50 paths25 endpoints
- CYP11B2ProteinUNIPROT:P19099metabolized byInferred only24 paths24 endpoints
- ABCB1ProteinUNIPROT:P08183transported byInferred only21 paths20 endpoints
- CYP11B1ProteinUNIPROT:P15538metabolized byInferred only21 paths21 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: "Cyproterone". Source: LiverTox Master List (NBK571102).
The document·Public Domain (NLM/NIH)·Transcribed, not assessed
Chemical structure
- 17alpha-hydroxyprogesterone has the functional parent progesteroneCompoundChEBI CHEBI:17252Inferred only
Statements
24 statements
24 statements · 2 reference databases · Subject: 17alpha-hydroxyprogesterone · Sources: Human-GEM, Rhea
- (17R,20S)-17,20-dihydroxypregn-4-en-3-one is converted to 17alpha-hydroxyprogesteroneCompoundRhea RHEA:15853Inferred only
- 17alpha-hydroxyprogesterone is converted to (17R,20S)-17,20-dihydroxypregn-4-en-3-oneCompoundRhea RHEA:15853Inferred only
- 17alpha-hydroxyprogesterone is converted to (17R,20S)-17,20-dihydroxypregn-4-en-3-oneCompoundRhea RHEA:15857Inferred only
- (17R,20S)-17,20-dihydroxypregn-4-en-3-one is converted to 17alpha-hydroxyprogesteroneCompoundHuman-GEM MAR10072Inferred only
- 17alpha-hydroxyprogesterone is converted to 11-deoxycortisolCompoundHuman-GEM MAR01988Inferred only
- 17alpha-hydroxyprogesterone is converted to 11-deoxycortisolCompoundHuman-GEM MAR07928Inferred only
- 17alpha-hydroxypregnenolone is converted to 17alpha-hydroxyprogesteroneCompoundHuman-GEM MAR07939Inferred only
- 17alpha-hydroxypregnenolone is converted to 17alpha-hydroxyprogesteroneCompoundHuman-GEM MAR07973Inferred only
- progesterone is converted to 17alpha-hydroxyprogesteroneCompoundHuman-GEM MAR01981Inferred only
- progesterone is converted to 17alpha-hydroxyprogesteroneCompoundHuman-GEM MAR07937Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP11B1ProteinHuman-GEM MAR01989Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP11B2ProteinHuman-GEM MAR01989Inferred only
Show the remaining 12
- 17alpha-hydroxyprogesterone is metabolised by CYP17A1ProteinHuman-GEM MAR07938Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP17A1ProteinRhea RHEA:53216Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP17A1ProteinRhea RHEA:14753Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP17A1ProteinHuman-GEM MAR02723Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP17A1ProteinHuman-GEM MAR01987Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP17A1ProteinHuman-GEM MAR01985Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP21A2ProteinHuman-GEM MAR07928Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP21A2ProteinHuman-GEM MAR01988Inferred only
- 17alpha-hydroxyprogesterone is metabolised by CYP21A2ProteinRhea RHEA:50308Inferred only
- 17alpha-hydroxyprogesterone is a substrate of AKR1C1ProteinRhea RHEA:15857Inferred only
- 17alpha-hydroxyprogesterone is a substrate of AKR1C1ProteinRhea RHEA:15853Inferred only
- 17alpha-hydroxyprogesterone is transported by ABCB1ProteinHuman-GEM MAR11770Inferred only
Reactions
22 reactions
proton+NADPH(4-)+dioxygen+progesterone17alpha-hydroxyprogesterone+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.14.19cytosol
Human-GEM MAR01981CC BY 4.0Reference data
MAM02761c17alpha-hydroxyprogesterone
Reaction pageLeft to rightBalancedEC 5.3.3.1cytosol
Human-GEM MAR01983CC 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
17alpha-hydroxyprogesterone+proton+NADPH(4-)+dioxygen11-deoxycortisol+water+NADP(3-)
Catalysed by CYP21A2
Reaction pageLeft to rightBalancedEC 1.14.14.16cytosol
Human-GEM MAR01988CC BY 4.0Reference data
17alpha-hydroxyprogesterone+proton+NADPH(4-)+dioxygenMAM00603c+water+NADP(3-)
Catalysed by CYP11B1 or CYP11B2
Reaction pageLeft to rightBalancedEC 1.14.15.4cytosol
Human-GEM MAR01989CC 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-)+dioxygen11-deoxycortisol+water+NADP(3-)
Catalysed by CYP21A2
Reaction pageLeft to rightBalancedEC 1.14.14.16endoplasmic reticulum
Human-GEM MAR07928CC BY 4.0Reference data
proton+NADPH(4-)+dioxygen+progesterone17alpha-hydroxyprogesterone+water+NADP(3-)
Catalysed by CYP17A1
Reaction pageLeft to rightBalancedEC 1.14.14.19endoplasmic reticulum
Human-GEM MAR07937CC 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
17alpha-hydroxypregnenolone+NAD(+)17alpha-hydroxyprogesterone+proton+NADH(2-)
Reaction pageLeft to rightBalancedEC 5.3.3.1endoplasmic reticulum
Human-GEM MAR07939CC BY 4.0Reference data
17alpha-hydroxypregnenolone+NAD(+)17alpha-hydroxyprogesterone+proton+NADH(2-)
Reaction pageLeft to rightBalancedEC 5.3.3.1cytosol
Human-GEM MAR07973CC BY 4.0Reference data
Where it reaches
3 systems, 6 regions, 11 tissues, 11 transporter routes — routes, not measurements: transporters known to carry 17alpha-hydroxyprogesterone are expressed there, and no source reports it arriving.
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Other names
9 names
Resolves to: 17alpha-hydroxyprogesterone
- Also called
- 17-Hydroxypregn-4-en-3,20-dione17-hydroxyprogesterone17alpha-Hydroxy-4-pregnene-3,20-dione17alpha-Hydroxy-progesteronedelta(4)-Pregnene-17alpha-ol-3,20-dionehydroxyprogesteronePregn-4-ene-3,20-dione-17-olST 21:3;O3
- Systematic name
- 17-hydroxypregn-4-ene-3,20-dione