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	No supplier information found for this compound.

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

1 2 1 0 0 0 0

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): 19 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

Jmol script terminated

Molfile expand

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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

Dawson MI (2000)
The importance of vitamin A in nutrition.
Current pharmaceutical design 6, 311-325 [PubMed:10637381]
[show Abstract]

Kieu NT, Yurie K, Hung NT, Yamamoto S, Chuyen NV (2002)
Simultaneous analysis of retinol, beta-carotene and tocopherol levels in serum of Vietnamese populations with different incomes.
Asia Pacific journal of clinical nutrition 11, 92-97 [PubMed:12074187]
[show Abstract]

Last Modified

28 July 2021

CHEBI:17336 - all-trans-retinol

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