Compound
5alpha-pregnane-3,20-dione
A biologically active 5-alpha-reduced metabolite of plasma progesterone. It is the immediate precursor of 5-alpha-pregnan-3-alpha-ol-20-one (allopregnanolone), a neuroactive steroid that binds with gaba(A) receptor.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C21H32O2
- Mass
- 316.485 g/mol
- Charge
- 0
- InChIKey
- XMRPGKVKISIQBV-BJMCWZGWSA-N
- SMILES
- [H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@@H](C(C)=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
9 entities
9 entities reached.
0 reported hops9 assembled from the scaffold
- AKR1C4ProteinUNIPROT:P17516substrate ofInferred only84 paths21 endpoints
- AKR1C1ProteinUNIPROT:Q04828substrate ofInferred only75 paths25 endpoints
- AKR1C2ProteinUNIPROT:P52895substrate ofInferred only48 paths16 endpoints
- AKR1C3ProteinUNIPROT:P42330substrate ofInferred only35 paths35 endpoints
- ABCB1ProteinUNIPROT:P08183transported byInferred only21 paths20 endpoints
- SRD5A3ProteinUNIPROT:Q9H8P0substrate ofInferred only18 paths18 endpoints
- SRD5A2ProteinUNIPROT:P31213substrate ofInferred only13 paths13 endpoints
- SRD5A1ProteinUNIPROT:P18405substrate ofInferred only11 paths11 endpoints
- DHRS9ProteinUNIPROT:Q9BPW9substrate ofInferred only9 paths9 endpoints
What the reference databases state
Chemical structure
- 5alpha-pregnane-3,20-dione has the functional parent progesteroneCompoundChEBI CHEBI:28952Inferred only
Statements
27 statements
27 statements · 2 reference databases · Subject: 5alpha-pregnane-3,20-dione · Sources: Human-GEM, Rhea
- 20alpha-hydroxy-5alpha-pregnane-3-one is converted to 5alpha-pregnane-3,20-dioneCompoundHuman-GEM MAR10071Inferred only
- 5alpha-pregnane-3,20-dione is converted to 20alpha-hydroxy-5alpha-pregnane-3-oneCompoundRhea RHEA:84163Inferred only
- 3alpha-hydroxy-5alpha-pregnan-20-one is converted to 5alpha-pregnane-3,20-dioneCompoundRhea RHEA:41980Inferred only
- 5alpha-pregnane-3,20-dione is converted to 3alpha-hydroxy-5alpha-pregnan-20-oneCompoundHuman-GEM MAR02003Inferred only
- 5alpha-pregnane-3,20-dione is converted to 3alpha-hydroxy-5alpha-pregnan-20-oneCompoundHuman-GEM MAR02004Inferred only
- 5alpha-pregnane-3,20-dione is converted to 3alpha-hydroxy-5alpha-pregnan-20-oneCompoundRhea RHEA:84155Inferred only
- 3alpha-hydroxy-5alpha-pregnan-20-one is converted to 5alpha-pregnane-3,20-dioneCompoundHuman-GEM MAR02003Inferred only
- 3alpha-hydroxy-5alpha-pregnan-20-one is converted to 5alpha-pregnane-3,20-dioneCompoundHuman-GEM MAR02004Inferred only
- 5alpha-pregnane-3,20-dione is converted to progesteroneCompoundHuman-GEM MAR02002Inferred only
- progesterone is converted to 5alpha-pregnane-3,20-dioneCompoundHuman-GEM MAR02002Inferred only
- progesterone is converted to 5alpha-pregnane-3,20-dioneCompoundRhea RHEA:21952Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C1ProteinRhea RHEA:84163Inferred only
Show the remaining 15
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C1ProteinRhea RHEA:84155Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C1ProteinHuman-GEM MAR02003Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C2ProteinHuman-GEM MAR02003Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C2ProteinRhea RHEA:84163Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C2ProteinRhea RHEA:84155Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C3ProteinHuman-GEM MAR02003Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C4ProteinRhea RHEA:84155Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C4ProteinRhea RHEA:84163Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C4ProteinHuman-GEM MAR02003Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of AKR1C4ProteinHuman-GEM MAR02004Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of DHRS9ProteinRhea RHEA:41988Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of SRD5A1ProteinHuman-GEM MAR02002Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of SRD5A2ProteinHuman-GEM MAR02002Inferred only
- 5alpha-pregnane-3,20-dione is a substrate of SRD5A3ProteinHuman-GEM MAR02002Inferred only
- 5alpha-pregnane-3,20-dione is transported by ABCB1ProteinHuman-GEM MAR11772Inferred only
Reactions
13 reactions
5alpha-pregnane-3,20-dione+NADP(3-)proton+NADPH(4-)+progesterone
Catalysed by SRD5A3 or SRD5A1 or SRD5A2
Reaction pageReversibleBalancedEC 1.3.1.22cytosol
Human-GEM MAR02002CC BY 4.0Reference data
3alpha-hydroxy-5alpha-pregnan-20-one+NADP(3-)5alpha-pregnane-3,20-dione+proton+NADPH(4-)
Catalysed by AKR1C2 or AKR1C1 or AKR1C3 or AKR1C4
Reaction pageReversibleBalancedEC 1.1.1.213cytosol
Human-GEM MAR02003CC BY 4.0Reference data
5alpha-pregnane-3,20-dione+proton+NADH(2-)3alpha-hydroxy-5alpha-pregnan-20-one+NAD(+)
Catalysed by AKR1C4
Reaction pageReversibleBalancedEC 1.1.1.50cytosol
Human-GEM MAR02004CC BY 4.0Reference data
NADP(3-)+20alpha-hydroxy-5alpha-pregnane-3-one5alpha-pregnane-3,20-dione+proton+NADPH(4-)
Catalysed by AKR1C3
Reaction pageLeft to rightBalancedEC 1.1.1.-cytosol
Human-GEM MAR10071CC BY 4.0Reference data
5alpha-pregnane-3,20-dione+ATP+water5alpha-pregnane-3,20-dione+ADP+proton+phosphate(3-)
Transported by ABCB1
Reaction pageLeft to rightBalancedcytosol, extracellular space
Human-GEM MAR11772CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR11871CC BY 4.0Reference data
CHEBI:11909+NADP(3-)5alpha-pregnane-3,20-dione+NADPH(4-)+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:18137CC BY 4.0Reference data
5alpha-pregnane-3,20-dione+NADP(3-)progesterone+NADPH(4-)+hydron
Reaction pageRight to leftBalanced
Rhea RHEA:21952CC BY 4.0Reference data
3alpha-hydroxy-5alpha-pregnan-20-one+NAD(1-)5alpha-pregnane-3,20-dione+NADH(2-)+hydron
Catalysed by HSD17B6 or HSD17B10 or DHRS9
Reaction pageLeft to rightBalanced
Rhea RHEA:41980CC BY 4.0Reference data
CHEBI:11909+NAD(1-)5alpha-pregnane-3,20-dione+NADH(2-)+hydron
Catalysed by DHRS9
Reaction pageDirection not assertedBalanced
Rhea RHEA:41988CC BY 4.0Reference data
CHEBI:78594+NAD(1-)5alpha-pregnane-3,20-dione+NADH(2-)+hydron
Catalysed by HSD17B10
Reaction pageLeft to rightBalanced
Rhea RHEA:42008CC BY 4.0Reference data
5alpha-pregnane-3,20-dione+NADPH(4-)+hydron3alpha-hydroxy-5alpha-pregnan-20-one+NADP(3-)
Catalysed by AKR1C4 or AKR1C2 or AKR1C1
Reaction pageLeft to rightBalanced
Rhea RHEA:84155CC BY 4.0Reference data
Where it reaches
3 systems, 6 regions, 11 tissues, 11 transporter routes — routes, not measurements: transporters known to carry 5alpha-pregnane-3,20-dione are expressed there, and no source reports it arriving.
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Other names
9 names
Resolves to: 5alpha-pregnane-3,20-dione
- Also called
- 3,20-allopregnanedione3,20-dioxo-5alpha-pregnane3,20-dioxo-5α-pregnane5-alpha-dihydroprogesterone5-α-dihydroprogesterone5alpha-dihydroprogesterone5α-dihydroprogesteroneST 21:2;O2
- Systematic name
- 5α-pregnane-3,20-dione