all-trans-retinol (CHEBI:17336)

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CHEBI:17336 - all-trans-retinol

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ChEBI Name	all-trans-retinol

ChEBI ID	CHEBI:17336

ChEBI ASCII Name	all-trans-retinol

Definition	A retinol in which all four exocyclic double bonds have E- (trans-) geometry.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:8816, CHEBI:12783, CHEBI:22349

Supplier Information	ChemicalBook:CB8194893, ChemicalBook:CB3512063, eMolecules:485716, eMolecules:6760397, ZINC000003831417

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

RTL - Ideal conformer

Mrv1927 07282109493D

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Time for openFile(RTL - Ideal conformer

Mrv1927 07282109493D

51 51 0 0 0 0 999 V2000

-4.4350 0.9020 -0.4080 C 0 0 2 0 0 0 0 0 0 0 0 0

-5.5830 0.1420 -1.0750 C 0 0 1 0 0 0 0 0 0 0 0 0

-6.0840 -0.9340 -0.1030 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.9930 -1.9970 0.0490 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.6750 -1.3450 0.3490 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.4270 -0.0640 0.1430 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0950 0.4420 0.4700 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9980 -0.1250 -0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2880 0.3340 0.2570 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3880 -0.2340 -0.3060 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6740 0.2250 0.0420 C 0 0 0 0 0 0 0 0 0 0 0 0

3.7720 -0.3410 -0.5190 C 0 0 0 0 0 0 0 0 0 0 0 0

5.1060 0.1350 -0.1580 C 0 0 0 0 0 0 0 0 0 0 0 0

6.1860 -0.4230 -0.7110 C 0 0 0 0 0 0 0 0 0 0 0 0

7.5610 0.0680 -0.3380 C 0 0 1 0 0 0 0 0 0 0 0 0

8.4180 -1.0510 -0.1020 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.9890 1.7620 0.7300 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.7590 1.8070 -1.4410 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5720 -2.2000 0.9170 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4450 1.4550 1.2520 C 0 0 0 0 0 0 0 0 0 0 0 0

5.2620 1.2550 0.8370 C 0 0 0 0 0 0 0 0 0 0 0 0

-6.3950 0.8320 -1.3060 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.2280 -0.3290 -1.9910 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.2930 -0.4830 0.8670 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.9890 -1.3930 -0.5000 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.2570 -2.6710 0.8640 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.9130 -2.5670 -0.8760 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9840 1.2670 1.1580 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1100 -0.9280 -0.8050 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2760 -1.0370 -1.0190 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7870 1.0280 0.7560 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6590 -1.1440 -1.2320 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0740 -1.2260 -1.4240 H 0 0 0 0 0 0 0 0 0 0 0 0

7.9650 0.6690 -1.1530 H 0 0 0 0 0 0 0 0 0 0 0 0

7.4980 0.6740 0.5650 H 0 0 0 0 0 0 0 0 0 0 0 0

9.3220 -0.8090 0.1420 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.4770 1.1210 1.4650 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1730 2.3050 1.2060 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.7130 2.4720 0.3300 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.5070 2.4520 -1.9030 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0050 2.4200 -0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2850 1.1930 -2.2070 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9540 -3.2010 1.1150 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7520 -2.2590 0.2010 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2120 -1.7580 1.8470 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5200 1.0400 2.2570 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3480 2.0200 1.0240 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4210 2.1150 1.1950 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3370 0.8400 1.8430 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1660 1.8210 0.6090 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3960 1.9150 0.7810 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 6 1 0 0 0 0

1 17 1 0 0 0 0

1 18 1 0 0 0 0

2 3 1 0 0 0 0

2 22 1 0 0 0 0

2 23 1 0 0 0 0

3 4 1 0 0 0 0

3 24 1 0 0 0 0

3 25 1 0 0 0 0

4 5 1 0 0 0 0

4 26 1 0 0 0 0

4 27 1 0 0 0 0

5 6 2 0 0 0 0

5 19 1 0 0 0 0

6 7 1 0 0 0 0

7 8 2 0 0 0 0

7 28 1 0 0 0 0

8 9 1 0 0 0 0

8 29 1 0 0 0 0

9 10 2 0 0 0 0

9 20 1 0 0 0 0

10 11 1 0 0 0 0

10 30 1 0 0 0 0

11 12 2 0 0 0 0

11 31 1 0 0 0 0

12 13 1 0 0 0 0

12 32 1 0 0 0 0

13 14 2 0 0 0 0

13 21 1 0 0 0 0

14 15 1 0 0 0 0

14 33 1 0 0 0 0

15 16 1 0 0 0 0

15 34 1 0 0 0 0

15 35 1 0 0 0 0

16 36 1 0 0 0 0

17 37 1 0 0 0 0

17 38 1 0 0 0 0

17 39 1 0 0 0 0

18 40 1 0 0 0 0

18 41 1 0 0 0 0

18 42 1 0 0 0 0

19 43 1 0 0 0 0

19 44 1 0 0 0 0

19 45 1 0 0 0 0

20 46 1 0 0 0 0

20 47 1 0 0 0 0

20 48 1 0 0 0 0

21 49 1 0 0 0 0

21 50 1 0 0 0 0

21 51 1 0 0 0 0

M END): 18 ms

reading 51 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

51 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

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Molfile expand

Wikipedia	License
Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family that is found in food and used as a dietary supplement. Retinol or other forms of vitamin A are needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development. Dietary sources include fish, dairy products, and meat. As a supplement it is used to treat and prevent vitamin A deficiency, especially that which results in xerophthalmia. It is taken by mouth or by injection into a muscle. As an ingredient in skin-care products, it is used to reduce wrinkles and other effects of skin aging. Retinol at normal doses is well tolerated. High doses may cause enlargement of the liver, dry skin, and hypervitaminosis A. High doses during pregnancy may harm the fetus. The body converts retinol to retinal and retinoic acid, through which it acts. Retinol was discovered in 1909, isolated in 1931, and first made in 1947. It is on the World Health Organization's List of Essential Medicines. Retinol is available as a generic medication and over the counter. In 2021, vitamin A was the 298th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.
Read full article at Wikipedia

Formula

C20H30O

Net Charge

Average Mass

286.459

Monoisotopic Mass

286.22967

InChI

InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChIKey

FPIPGXGPPPQFEQ-OVSJKPMPSA-N

SMILES

C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Taxus chinensis (NCBI:txid29808)	See: PubMed
Pandanus tectorius (NCBI:txid4726)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606)	Found in saliva (UBERON:0001836). See: Dame, ZT. et al. (2014) The Human Saliva Metabolome (manuscript in preparation)

Roles Classification
Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via retinol ) plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via vitamin A ) fat-soluble vitamin (role) Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess. (via vitamin A )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	all-trans-retinol (CHEBI:17336) has role human metabolite (CHEBI:77746) all-trans-retinol (CHEBI:17336) has role mouse metabolite (CHEBI:75771) all-trans-retinol (CHEBI:17336) has role plant metabolite (CHEBI:76924) all-trans-retinol (CHEBI:17336) is a retinol (CHEBI:50211) all-trans-retinol (CHEBI:17336) is a vitamin A (CHEBI:12777)

Incoming	all-trans-3,4-didehydroretinol (CHEBI:132246) has functional parent all-trans-retinol (CHEBI:17336) all-trans-3-hydroxyretinol (CHEBI:156530) has functional parent all-trans-retinol (CHEBI:17336) all-trans-4-hydroxyretinol (CHEBI:132259) has functional parent all-trans-retinol (CHEBI:17336) all-trans-4-oxoretinol (CHEBI:44597) has functional parent all-trans-retinol (CHEBI:17336) all-trans-retinyl ester (CHEBI:63410) has functional parent all-trans-retinol (CHEBI:17336) all-trans-retinyl linoleate (CHEBI:70762) has functional parent all-trans-retinol (CHEBI:17336) all-trans-retinyl oleate (CHEBI:70760) has functional parent all-trans-retinol (CHEBI:17336) all-trans-retinyl palmitate (CHEBI:17616) has functional parent all-trans-retinol (CHEBI:17336) all-trans-retinyl stearate (CHEBI:70761) has functional parent all-trans-retinol (CHEBI:17336) retinyl acetate (CHEBI:32095) has functional parent all-trans-retinol (CHEBI:17336)

IUPAC Name

all-trans-retinol

INNs	Sources
retinol	WHO MedNet
rétinol	WHO MedNet
retinol	WHO MedNet
retinolum	WHO MedNet

Synonyms	Sources
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol	IUPAC
(all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol	HMDB
all-trans retinol	ChemIDplus
all-trans-Retinol	KEGG COMPOUND
all-trans-retinol	UniProt
all-trans-retinyl alcohol	ChemIDplus
all-trans-vitamin A	ChemIDplus
all-trans-vitamin A alcohol	NIST Chemistry WebBook
retinol (vit A)	DrugCentral
trans-retinol	HMDB
vitamin A	KEGG COMPOUND
vitamin A alcohol	ChemIDplus
Vitamin A1	KEGG COMPOUND
vitamin A₁	ChEBI
vitamin A1 alcohol	ChemIDplus

Brand Names	Sources
Alphalin	ChemIDplus
Aquasol A	KEGG DRUG
Chocola A	ChemIDplus

Manual Xrefs	Databases
2831	DrugCentral
393012	ChemSpider
C00031437	KNApSAcK
C00473	KEGG COMPOUND
C17276	KEGG COMPOUND
CPD-13524	MetaCyc
D00069	KEGG DRUG
D06543	KEGG DRUG
DB00162	DrugBank
HMDB0000305	HMDB
LMPR01090001	LIPID MAPS
Retinol	Wikipedia
RTL	PDBeChem
View more database links

Registry Numbers	Types	Sources
11103-57-4	CAS Registry Number	ChemIDplus
247497	Gmelin Registry Number	Gmelin
403040	Beilstein Registry Number	Beilstein
68-26-8	CAS Registry Number	ChemIDplus
68-26-8	CAS Registry Number	NIST Chemistry WebBook

Citations

Moschetta A, vanBerge-Henegouwen GP, Portincasa P, Renooij WL, Groen AK, van Erpecum KJ (2001)
Hydrophilic bile salts enhance differential distribution of sphingomyelin and phosphatidylcholine between micellar and vesicular phases: potential implications for their effects in vivo.
Journal of hepatology 34, 492-499 [PubMed:11394647]
[show Abstract]

Last Modified

28 July 2021

ChEBI

CHEBI:17336 - all-trans-retinol

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