Compound

11-cis-retinol

Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.

Definition from MeSH (D014801), National Library of Medicine, read 2026-09-23. NLM revises MeSH; this copy may not reflect its current record.

CHEBI:16302ChEBI

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Structure

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A generated conformer of 11-cis-retinol — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C20H30O
Mass: 286.459 g/mol
Charge: 0
InChIKey: FPIPGXGPPPQFEQ-IOUUIBBYSA-N
SMILES: CC1=C(/C=C/C(C)=C/C=CC(C)=CCO)C(C)(C)CCC1
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

19 entities

19 entities reached.

0 reported hops19 assembled from the scaffold

Show the remaining 7

What the reference databases state

Chemical structure

11-cis-retinyl hexadecanoate has the functional parent 11-cis-retinolCompoundChEBI CHEBI:16254Inferred only
11-cis-retinyl tetradecanoate has the functional parent 11-cis-retinolCompoundChEBI CHEBI:138676Inferred only

Statements

53 statements

53 statements · 2 reference databases · Subject: 11-cis-retinol · Sources: Human-GEM, Rhea

Order

11-cis-retinol is converted to 11-cis-retinalCompoundRhea RHEA:42060Inferred only
11-cis-retinol is converted to 11-cis-retinalCompoundRhea RHEA:54912Inferred only
11-cis-retinol is converted to 11-cis-retinalCompoundHuman-GEM MAR08709Inferred only
11-cis-retinol is converted to 11-cis-retinalCompoundHuman-GEM MAR06638Inferred only
11-cis-retinal is converted to 11-cis-retinolCompoundHuman-GEM MAR06638Inferred only
11-cis-retinal is converted to 11-cis-retinolCompoundHuman-GEM MAR08709Inferred only
11-cis-retinal is converted to 11-cis-retinolCompoundRhea RHEA:42060Inferred only
11-cis-retinal is converted to 11-cis-retinolCompoundRhea RHEA:54912Inferred only
11-cis-retinol is converted to 13-cis-retinolCompoundRhea RHEA:55356Inferred only
11-cis-retinol is converted to 9-cis-retinolCompoundRhea RHEA:55360Inferred only
11-cis-retinol is converted to all-trans-retinolCompoundHuman-GEM MAR08711Inferred only
all-trans-retinol is converted to 11-cis-retinolCompoundRhea RHEA:19141Inferred only

Show the remaining 41

11-cis-retinol is converted to all-trans-retinolCompoundRhea RHEA:19141Inferred only
all-trans-retinol is converted to 11-cis-retinolCompoundHuman-GEM MAR08711Inferred only
11-cis-retinol is a substrate of AWAT1ProteinHuman-GEM MAR06671Inferred only
11-cis-retinol is a substrate of AWAT1ProteinHuman-GEM MAR06639Inferred only
11-cis-retinol is a substrate of AWAT2ProteinRhea RHEA:55272Inferred only
11-cis-retinol is a substrate of AWAT2ProteinHuman-GEM MAR06671Inferred only
11-cis-retinol is a substrate of AWAT2ProteinRhea RHEA:55324Inferred only
11-cis-retinol is a substrate of AWAT2ProteinRhea RHEA:77767Inferred only
11-cis-retinol is a substrate of AWAT2ProteinHuman-GEM MAR06639Inferred only
11-cis-retinol is a substrate of DEGS1ProteinRhea RHEA:55360Inferred only
11-cis-retinol is a substrate of DEGS1ProteinRhea RHEA:19141Inferred only
11-cis-retinol is a substrate of DEGS1ProteinRhea RHEA:55356Inferred only
11-cis-retinol is a substrate of DGAT1ProteinHuman-GEM MAR06671Inferred only
11-cis-retinol is a substrate of DGAT1ProteinHuman-GEM MAR06639Inferred only
11-cis-retinol is a substrate of DGAT2ProteinHuman-GEM MAR06671Inferred only
11-cis-retinol is a substrate of DGAT2ProteinHuman-GEM MAR06639Inferred only
11-cis-retinol is a substrate of DHRS4ProteinHuman-GEM MAR08709Inferred only
11-cis-retinol is a substrate of DHRS4ProteinHuman-GEM MAR06638Inferred only
11-cis-retinol is a substrate of DHRS4L2ProteinHuman-GEM MAR08709Inferred only
11-cis-retinol is a substrate of DHRS4L2ProteinHuman-GEM MAR06638Inferred only
11-cis-retinol is a substrate of HSD17B6ProteinHuman-GEM MAR08709Inferred only
11-cis-retinol is a substrate of HSD17B6ProteinHuman-GEM MAR06638Inferred only
11-cis-retinol is a substrate of LRATProteinHuman-GEM MAR06671Inferred only
11-cis-retinol is a substrate of LRATProteinHuman-GEM MAR06639Inferred only
11-cis-retinol is a substrate of RBP1ProteinHuman-GEM MAR06639Inferred only
11-cis-retinol is a substrate of RBP2ProteinHuman-GEM MAR06639Inferred only
11-cis-retinol is a substrate of RBP3ProteinHuman-GEM MAR06638Inferred only
11-cis-retinol is a substrate of RBP3ProteinHuman-GEM MAR08709Inferred only
11-cis-retinol is a substrate of RDH11ProteinRhea RHEA:54912Inferred only
11-cis-retinol is a substrate of RDH12ProteinRhea RHEA:54912Inferred only
11-cis-retinol is a substrate of RDH14ProteinRhea RHEA:54912Inferred only
11-cis-retinol is a substrate of RDH16ProteinHuman-GEM MAR08709Inferred only
11-cis-retinol is a substrate of RDH16ProteinHuman-GEM MAR06638Inferred only
11-cis-retinol is a substrate of RDH16ProteinRhea RHEA:42060Inferred only
11-cis-retinol is a substrate of RDH5ProteinHuman-GEM MAR08709Inferred only
11-cis-retinol is a substrate of RDH5ProteinHuman-GEM MAR06638Inferred only
11-cis-retinol is a substrate of RDH5ProteinRhea RHEA:42060Inferred only
11-cis-retinol is a substrate of RLBP1ProteinHuman-GEM MAR08709Inferred only
11-cis-retinol is a substrate of RLBP1ProteinHuman-GEM MAR06638Inferred only
11-cis-retinol is a substrate of RPE65ProteinRhea RHEA:31775Inferred only
11-cis-retinol is a substrate of RPE65ProteinRhea RHEA:31771Inferred only

Reactions

21 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
11-cis-retinol
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR00694CC BY 4.0Reference data
11-cis-retinol+1,2-diacyl-sn-glycero-3-phosphocholine(1+)1-O-acyl-sn-glycero-3-phosphocholine(1+)+an all-trans-retinyl ester
Reaction pageLeft to rightBalance undeterminableEC 1.14.14.1cytosol
Human-GEM MAR01506CC BY 4.0Reference data
water+an all-trans-retinyl ester11-cis-retinol+proton+fatty acid
Catalysed by RPE65
Reaction pageLeft to rightBalance undeterminableEC 3.1.1.64cytosol
Human-GEM MAR06637CC BY 4.0Reference data
11-cis-retinal+proton+NADH(2-)11-cis-retinol+NAD(+)
Catalysed by HSD17B6 or RDH5 or RDH16 or RLBP1 or DHRS4 or DHRS4L2 or RBP3
Reaction pageReversibleBalancedEC 1.1.1.105cytosol
Human-GEM MAR06638CC BY 4.0Reference data
11-cis-retinol+1,2-diacyl-sn-glycero-3-phosphocholine(1+)MAM00535c+an all-trans-retinyl ester
Catalysed by DGAT2 or RBP2 or RBP1 or LRAT or AWAT2 or DGAT1 or AWAT1
Reaction pageLeft to rightBalance undeterminableEC 2.3.1.135, 2.3.1.75cytosol
Human-GEM MAR06639CC BY 4.0Reference data
11-cis-retinol+palmitoyl-CoA11-cis-retinyl hexadecanoate+CHEBI:1146900
Catalysed by DGAT2 or LRAT or AWAT2 or DGAT1 or AWAT1
Reaction pageReversibleBalancedEC 2.3.1.75, 2.3.1.76, 2.3.1.135cytosol
Human-GEM MAR06671CC BY 4.0Reference data
11-cis-retinal+proton+NADPH(4-)11-cis-retinol+NADP(3-)
Catalysed by HSD17B6 or RDH5 or RDH16 or RLBP1 or DHRS4 or DHRS4L2 or RBP3
Reaction pageReversibleBalancedEC 1.1.1.105cytosol
Human-GEM MAR08709CC BY 4.0Reference data
11-cis-retinolall-trans-retinol
Reaction pageReversibleBalancedcytosol
Human-GEM MAR08711CC 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
all-trans-retinol11-cis-retinol
Catalysed by DEGS1
Reaction pageReversibleBalanced
Rhea RHEA:19141CC BY 4.0Reference data
11-cis-retinyl hexadecanoate+water11-cis-retinol+hexadecanoate+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:19697CC BY 4.0Reference data

Show the remaining 9

Other names

2 names

Resolves to: 11-cis-retinol

Also called: 11Z-retinol
Systematic name: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol