Compound
all-trans-retinal
A diterpene derived from the carotenoid vitamin A which functions as the active component of the visual cycle. It is the prosthetic group of rhodopsin (i.e., covalently bonded to ROD opsin as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C20H28O
- Mass
- 284.443 g/mol
- Charge
- 0
- InChIKey
- NCYCYZXNIZJOKI-OVSJKPMPSA-N
- SMILES
- [H]C(=O)/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
22 entities
22 entities reached.
0 reported hops22 assembled from the scaffold
- CYP1A2ProteinUNIPROT:P05177metabolized byInferred only117 paths39 endpoints
- ALDH1A1ProteinUNIPROT:P00352metabolized byInferred only93 paths31 endpoints
- all-trans-retinolCompoundCHEBI:17336converted toInferred only51 paths22 endpoints
- RBP1ProteinUNIPROT:P09455substrate ofInferred only50 paths25 endpoints
- ALDH1A2ProteinUNIPROT:O94788metabolized byInferred only36 paths12 endpoints
- CYP1A1ProteinUNIPROT:P04798metabolized byInferred only32 paths32 endpoints
- CYP1B1ProteinUNIPROT:Q16678metabolized byInferred only30 paths30 endpoints
- ALDH1A3ProteinUNIPROT:P47895metabolized byInferred only30 paths15 endpoints
- AKR1B1ProteinUNIPROT:P15121substrate ofInferred only22 paths22 endpoints
- RBP2ProteinUNIPROT:P50120substrate ofInferred only16 paths8 endpoints
- RDH11ProteinUNIPROT:Q8TC12substrate ofInferred only13 paths13 endpoints
- RDH10ProteinUNIPROT:Q8IZV5substrate ofInferred only12 paths12 endpoints
Show the remaining 10
- RDH12ProteinUNIPROT:Q96NR8substrate ofInferred only12 paths12 endpoints
- ALDH1B1ProteinUNIPROT:P30837metabolized byInferred only11 paths11 endpoints
- DHRS3ProteinUNIPROT:O75911substrate ofInferred only8 paths8 endpoints
- AKR1B10ProteinUNIPROT:O60218substrate ofInferred only7 paths7 endpoints
- RDH13ProteinUNIPROT:Q8NBN7substrate ofInferred only5 paths5 endpoints
- RDH8ProteinUNIPROT:Q9NYR8substrate ofInferred only5 paths5 endpoints
- AKR1B15ProteinUNIPROT:C9JRZ8substrate ofInferred only5 paths5 endpoints
- RDH14ProteinUNIPROT:Q9HBH5substrate ofInferred only4 paths4 endpoints
- HSD17B13ProteinUNIPROT:Q7Z5P4substrate ofInferred only3 paths3 endpoints
- ABCA4ProteinUNIPROT:P78363transported byInferred only2 paths2 endpoints
What the reference databases state
Chemical structure
- all-trans-4-hydroxyretinal has the functional parent all-trans-retinalCompoundChEBI CHEBI:139346Inferred only
Statements
54 statements
54 statements · 2 reference databases · Subject: all-trans-retinal · Sources: Human-GEM, Rhea
- all-trans-retinal is converted to 11-cis-retinalCompoundHuman-GEM MAR06651Inferred only
- all-trans-retinal is converted to 13-cis-retinalCompoundHuman-GEM MAR06673Inferred only
- 13-cis-retinal is converted to all-trans-retinalCompoundHuman-GEM MAR06673Inferred only
- 13-cis-retinal is converted to all-trans-retinalCompoundHuman-GEM MAR06672Inferred only
- all-trans-retinal is converted to 13-cis-retinalCompoundHuman-GEM MAR06672Inferred only
- all-trans-retinal is converted to 9-cis-retinalCompoundHuman-GEM MAR08702Inferred only
- all-trans-retinal is converted to 9-cis-retinalCompoundHuman-GEM MAR06650Inferred only
- 9-cis-retinal is converted to all-trans-retinalCompoundHuman-GEM MAR08702Inferred only
- all-trans-beta-carotene is converted to all-trans-retinalCompoundHuman-GEM MAR08697Inferred only
- all-trans-beta-carotene is converted to all-trans-retinalCompoundRhea RHEA:32887Inferred only
- all-trans-retinal is converted to all-trans-retinoateCompoundRhea RHEA:42080Inferred only
- all-trans-retinoate is converted to all-trans-retinalCompoundRhea RHEA:22520Inferred only
Show the remaining 42
- all-trans-retinal is converted to all-trans-retinoateCompoundRhea RHEA:22520Inferred only
- all-trans-retinal is converted to all-trans-retinoic acidCompoundHuman-GEM MAR06647Inferred only
- all-trans-retinal is converted to all-trans-retinoic acidCompoundHuman-GEM MAR06646Inferred only
- all-trans-retinal is converted to all-trans-retinoic acidCompoundHuman-GEM MAR08698Inferred only
- all-trans-retinoic acid is converted to all-trans-retinalCompoundHuman-GEM MAR08698Inferred only
- all-trans-retinol is converted to all-trans-retinalCompoundHuman-GEM MAR06630Inferred only
- all-trans-retinol is converted to all-trans-retinalCompoundHuman-GEM MAR06631Inferred only
- all-trans-retinal is converted to all-trans-retinolCompoundRhea RHEA:25033Inferred only
- all-trans-retinol is converted to all-trans-retinalCompoundRhea RHEA:21284Inferred only
- all-trans-retinol is converted to all-trans-retinalCompoundHuman-GEM MAR06632Inferred only
- all-trans-retinol is converted to all-trans-retinalCompoundHuman-GEM MAR06633Inferred only
- all-trans-retinal is metabolised by ALDH1A1ProteinRhea RHEA:42080Inferred only
- all-trans-retinal is metabolised by ALDH1A1ProteinHuman-GEM MAR06647Inferred only
- all-trans-retinal is metabolised by ALDH1A1ProteinHuman-GEM MAR06646Inferred only
- all-trans-retinal is metabolised by ALDH1A2ProteinHuman-GEM MAR06646Inferred only
- all-trans-retinal is metabolised by ALDH1A2ProteinHuman-GEM MAR06647Inferred only
- all-trans-retinal is metabolised by ALDH1A2ProteinRhea RHEA:42080Inferred only
- all-trans-retinal is metabolised by ALDH1A3ProteinRhea RHEA:42080Inferred only
- all-trans-retinal is metabolised by ALDH1A3ProteinHuman-GEM MAR06646Inferred only
- all-trans-retinal is metabolised by ALDH1B1ProteinRhea RHEA:42080Inferred only
- all-trans-retinal is metabolised by CYP1A1ProteinRhea RHEA:42088Inferred only
- all-trans-retinal is metabolised by CYP1A2ProteinRhea RHEA:42088Inferred only
- all-trans-retinal is metabolised by CYP1A2ProteinHuman-GEM MAR06649Inferred only
- all-trans-retinal is metabolised by CYP1A2ProteinHuman-GEM MAR06648Inferred only
- all-trans-retinal is metabolised by CYP1B1ProteinRhea RHEA:42088Inferred only
- all-trans-retinal is a substrate of AKR1B1ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of AKR1B10ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of AKR1B15ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of DHRS3ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of DHRS7ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of HSD17B13ProteinRhea RHEA:42080Inferred only
- all-trans-retinal is a substrate of RBP1ProteinHuman-GEM MAR06650Inferred only
- all-trans-retinal is a substrate of RBP1ProteinHuman-GEM MAR06651Inferred only
- all-trans-retinal is a substrate of RBP2ProteinHuman-GEM MAR06651Inferred only
- all-trans-retinal is a substrate of RBP2ProteinHuman-GEM MAR06650Inferred only
- all-trans-retinal is a substrate of RDH10ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of RDH11ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of RDH12ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of RDH13ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of RDH14ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is a substrate of RDH8ProteinRhea RHEA:25033Inferred only
- all-trans-retinal is transported by ABCA4ProteinHuman-GEM MAR09903Inferred only
Reactions
28 reactions
NADP(3-)+all-trans-retinolproton+NADPH(4-)+all-trans-retinal
Catalysed by RDH11 or DHRS9 or RDH8 or RDH10 or RDH12 or DHRS3
Reaction pageLeft to rightBalancedEC 1.1.1.300cytosol
Human-GEM MAR06630CC BY 4.0Reference data
NAD(+)+all-trans-retinolproton+NADH(2-)+all-trans-retinal
Catalysed by HSD17B6 or RDH5 or SDR16C5 or ADH6 or ADH1A or ADH7 or ADH1B or ADH5 or ADH4 or ADH1C
Reaction pageLeft to rightBalancedEC 1.1.1.1, 1.1.1.105cytosol
Human-GEM MAR06631CC BY 4.0Reference data
NADP(3-)+all-trans-retinolproton+NADPH(4-)+all-trans-retinal
Catalysed by RDH11 or DHRS9 or RDH8 or RDH10 or RDH12 or DHRS3
Reaction pageLeft to rightBalancedEC 1.1.1.300endoplasmic reticulum
Human-GEM MAR06632CC BY 4.0Reference data
NAD(+)+all-trans-retinolproton+NADH(2-)+all-trans-retinal
Catalysed by HSD17B6 or RDH5 or SDR16C5 or ADH6 or ADH1A or ADH7 or ADH1B or ADH5 or ADH4 or ADH1C
Reaction pageLeft to rightBalancedEC 1.1.1.1, 1.1.1.105endoplasmic reticulum
Human-GEM MAR06633CC BY 4.0Reference data
water+NAD(+)+all-trans-retinal2proton+NADH(2-)+all-trans-retinoic acid
Catalysed by ALDH1A2 or ALDH1A1 or ALDH1A3
Reaction pageLeft to rightBalancedEC 1.2.1.36cytosol
Human-GEM MAR06646CC BY 4.0Reference data
water+NAD(+)+all-trans-retinal2proton+NADH(2-)+all-trans-retinoic acid
Catalysed by ALDH1A2 or ALDH1A1
Reaction pageLeft to rightBalancedEC 1.2.1.36endoplasmic reticulum
Human-GEM MAR06647CC BY 4.0Reference data
proton+NADPH(4-)+dioxygen+all-trans-retinalMAM01024c+water+NADP(3-)
Catalysed by CYP1A2
Reaction pageLeft to rightBalancedEC 1.14.14.1cytosol
Human-GEM MAR06648CC BY 4.0Reference data
proton+NADPH(4-)+dioxygen+all-trans-retinalMAM01024r+water+NADP(3-)
Catalysed by CYP1A2
Reaction pageLeft to rightBalancedEC 1.14.14.1endoplasmic reticulum
Human-GEM MAR06649CC BY 4.0Reference data
all-trans-retinal9-cis-retinal
Reaction pageLeft to rightBalancedendoplasmic reticulum
Human-GEM MAR06650CC BY 4.0Reference data
all-trans-retinal11-cis-retinal
Reaction pageLeft to rightBalancedcytosol
Human-GEM MAR06651CC BY 4.0Reference data
13-cis-retinalall-trans-retinal
Reaction pageReversibleBalancedcytosol
Human-GEM MAR06672CC BY 4.0Reference data
13-cis-retinalall-trans-retinal
Reaction pageReversibleBalancedendoplasmic reticulum
Human-GEM MAR06673CC BY 4.0Reference data
Where it reaches
1 system, 1 region, 1 tissue, 1 transporter route — routes, not measurements: transporters known to carry all-trans-retinal are expressed there, and no source reports it arriving.
Loading the model…
Other names
16 names
Resolves to: all-trans-retinal
- Also called
- all-E-retinalall-trans-retinaldehydeall-trans-retineneall-trans-vitamin A aldehydeaxerophthalE-retinalretinalretinaldehyderetineneretinene 1retinyl aldehydetrans-retinaltrans-vitamin A aldehydevitamin A aldehydevitamin A1 aldehyde
- Systematic name
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal