Compound
9-cis-retinol
A retinol in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration.
Definition from ChEBI (CHEBI:78272), read 2026-09-23. CC BY 4.0.
Structure
- Class
- Organic compound
- Formula
- C20H30O
- Mass
- 286.459 g/mol
- Charge
- 0
- InChIKey
- FPIPGXGPPPQFEQ-MKOSUFFBSA-N
- SMILES
- CC1=C(/C=C/C(C)=CC=CC(C)=CCO)C(C)(C)CCC1
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
15 entities
15 entities reached.
0 reported hops15 assembled from the scaffold
- ADH4ProteinUNIPROT:P08319metabolized byInferred only42 paths14 endpoints
- AWAT2ProteinUNIPROT:Q6E213substrate ofInferred only36 paths12 endpoints
- RDH5ProteinUNIPROT:Q92781substrate ofInferred only32 paths16 endpoints
- RDH16ProteinUNIPROT:O75452substrate ofInferred only14 paths7 endpoints
- RLBP1ProteinUNIPROT:P12271substrate ofInferred only13 paths13 endpoints
- RDH11ProteinUNIPROT:Q8TC12substrate ofInferred only13 paths13 endpoints
- SDR16C5ProteinUNIPROT:Q8N3Y7substrate ofInferred only12 paths6 endpoints
- RDH12ProteinUNIPROT:Q96NR8substrate ofInferred only12 paths12 endpoints
- ADH7ProteinUNIPROT:P40394metabolized byInferred only12 paths12 endpoints
- DHRS4ProteinUNIPROT:Q9BTZ2substrate ofInferred only7 paths7 endpoints
- RBP3ProteinUNIPROT:P10745substrate ofInferred only5 paths5 endpoints
- RDH13ProteinUNIPROT:Q8NBN7substrate ofInferred only5 paths5 endpoints
What the reference databases state
Chemical structure
- 9-cis-retinyl hexadecanoate has the functional parent 9-cis-retinolCompoundChEBI CHEBI:138725Inferred only
- 9-cis-retinyl tetradecanoate has the functional parent 9-cis-retinolCompoundChEBI CHEBI:138691Inferred only
Statements
32 statements
32 statements · 2 reference databases · Subject: 9-cis-retinol · Sources: Human-GEM, Rhea
- 11-cis-retinol is converted to 9-cis-retinolCompoundRhea RHEA:55360Inferred only
- 9-cis-retinol is converted to 9-cis-retinalCompoundHuman-GEM MAR06644Inferred only
- 9-cis-retinol is converted to 9-cis-retinalCompoundHuman-GEM MAR01690Inferred only
- 9-cis-retinol is converted to 9-cis-retinalCompoundHuman-GEM MAR20003Inferred only
- 9-cis-retinol is converted to 9-cis-retinalCompoundRhea RHEA:42052Inferred only
- 9-cis-retinal is converted to 9-cis-retinolCompoundHuman-GEM MAR06644Inferred only
- 9-cis-retinal is converted to 9-cis-retinolCompoundRhea RHEA:54916Inferred only
- all-trans-retinol is converted to 9-cis-retinolCompoundRhea RHEA:55348Inferred only
- all-trans-retinol is converted to 9-cis-retinolCompoundHuman-GEM MAR06643Inferred only
- 9-cis-retinol is metabolised by ADH4ProteinRhea RHEA:42052Inferred only
- 9-cis-retinol is metabolised by ADH4ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is metabolised by ADH4ProteinHuman-GEM MAR20003Inferred only
Show the remaining 20
- 9-cis-retinol is metabolised by ADH7ProteinRhea RHEA:42052Inferred only
- 9-cis-retinol is a substrate of AWAT2ProteinRhea RHEA:55276Inferred only
- 9-cis-retinol is a substrate of AWAT2ProteinRhea RHEA:78263Inferred only
- 9-cis-retinol is a substrate of AWAT2ProteinRhea RHEA:55328Inferred only
- 9-cis-retinol is a substrate of DHRS4ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of DHRS4L2ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of HSD17B6ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of RBP3ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of RDH11ProteinHuman-GEM MAR01690Inferred only
- 9-cis-retinol is a substrate of RDH12ProteinHuman-GEM MAR01690Inferred only
- 9-cis-retinol is a substrate of RDH13ProteinHuman-GEM MAR01690Inferred only
- 9-cis-retinol is a substrate of RDH14ProteinHuman-GEM MAR01690Inferred only
- 9-cis-retinol is a substrate of RDH16ProteinRhea RHEA:42052Inferred only
- 9-cis-retinol is a substrate of RDH16ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of RDH5ProteinRhea RHEA:42052Inferred only
- 9-cis-retinol is a substrate of RDH5ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of RDH8ProteinHuman-GEM MAR01690Inferred only
- 9-cis-retinol is a substrate of RLBP1ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of SDR16C5ProteinHuman-GEM MAR06644Inferred only
- 9-cis-retinol is a substrate of SDR16C5ProteinHuman-GEM MAR01690Inferred only
Reactions
15 reactions
11-cis-retinol+all-trans-18-hydroxyretinoate+all-trans-18-hydroxyretinoate+MAM01008c+MAM01008r+MAM01022c+MAM01022r+MAM01024c+MAM01024r+MAM01026r+MAM01028c+MAM01028r+MAM01030c+MAM01030r+all-trans-4-oxoretinoate+all-trans-4-oxoretinoate+all-trans-4-oxoretinol+MAM01060c+9-cis-retinol+MAM02624cMAM03139c
Reaction pageLeft to rightBalance undeterminablecytosol, endoplasmic reticulum
Human-GEM MAR00023CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR00693CC BY 4.0Reference data
9-cis-retinol+1,2-diacyl-sn-glycero-3-phosphocholine(1+)1-O-acyl-sn-glycero-3-phosphocholine(1+)+MAM03315c
Reaction pageLeft to rightBalance undeterminableEC 5.4.99.7cytosol
Human-GEM MAR01507CC BY 4.0Reference data
9-cis-retinol+NADP(3-)9-cis-retinal+proton+NADPH(4-)
Catalysed by RDH11 or RDH8 or RDH12 or RDH13 or SDR16C5 or RDH14
Reaction pageLeft to rightBalancedEC 1.1.1.105cytosol
Human-GEM MAR01690CC BY 4.0Reference data
all-trans-retinol9-cis-retinol
Reaction pageLeft to rightBalancedcytosol
Human-GEM MAR06643CC BY 4.0Reference data
9-cis-retinal+proton+NADH(2-)9-cis-retinol+NAD(+)
Catalysed by HSD17B6 or RDH5 or RDH16 or RLBP1 or DHRS4 or SDR16C5 or DHRS4L2 or ADH4 or RBP3
Reaction pageReversibleBalancedEC 1.1.1.105cytosol
Human-GEM MAR06644CC BY 4.0Reference data
0.034511-cis-retinol+0.0172all-trans-18-hydroxyretinoate+0.0172all-trans-18-hydroxyretinoate+0.0172MAM00611c+0.0172MAM00611m+0.0172MAM00622c+0.0172MAM00622m+0.0345MAM00766c+0.0172MAM01008c+0.0172MAM01008r+0.0172MAM01022c+0.0172MAM01022r+0.0172MAM01024c+0.0172MAM01024r+0.0345MAM01026r+0.0172MAM01028c+0.0172MAM01028r+0.0172MAM01030c+0.0172MAM01030r+0.0172all-trans-4-oxoretinoate+0.0172all-trans-4-oxoretinoate+0.0345all-trans-4-oxoretinol+0.0345MAM01060c+0.03459-cis-retinol+0.0345biotin+0.0345MAM01600m+0.0345FADH2+0.0345MAM01924c+0.0345heme b+0.0345(S)-carnitine+0.0345(R)-lipoate+0.0345MAM02624c+0.0345CHEBI:18405+0.0345riboflavin+0.03455,6,7,8-tetrahydrobiopterin+0.03455,6,7,8-tetrahydrofolic acid+0.0345thiamine(1+) diphosphate+0.0345ubiquinolMAM10012c
Reaction pageLeft to rightBalance undeterminablecytosol, endoplasmic reticulum, mitochondrial matrix
Human-GEM MAR10065CC BY 4.0Reference data
9-cis-retinol+NAD(+)9-cis-retinal+proton+NADH(2-)
Catalysed by ADH4
Reaction pageLeft to rightBalancedEC 1.1.1.315nucleus
Human-GEM MAR20003CC BY 4.0Reference data
9-cis-retinol+NAD(1-)9-cis-retinal+NADH(2-)+hydron
Catalysed by RDH16 or ADH4 or ADH7 or RDH5
Reaction pageLeft to rightBalanced
Rhea RHEA:42052CC BY 4.0Reference data
9-cis-retinol+NADP(3-)9-cis-retinal+NADPH(4-)+hydron
Catalysed by AKR1B15 or AKR1B10 or AKR1B1 or AKR1C3 or RDH11 or RDH12 or RDH14
Reaction pageRight to leftBalanced
Rhea RHEA:54916CC BY 4.0Reference data
9-cis-retinol+tetradecanoyl-CoA9-cis-retinyl tetradecanoate+coenzyme A(4-)
Catalysed by AWAT2
Reaction pageLeft to rightBalanced
Rhea RHEA:55276CC BY 4.0Reference data
9-cis-retinol+hexadecanoyl-CoA9-cis-retinyl hexadecanoate+coenzyme A(4-)
Catalysed by AWAT2
Reaction pageLeft to rightBalanced
Rhea RHEA:55328CC BY 4.0Reference data
Other names
3 names
Resolves to: 9-cis-retinol
- Also called
- (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol(9cis)-retinol9Z-retinol