all-trans-retinal (CHEBI:17898)

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CHEBI:17898 - all-trans-retinal

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ChEBI Name	all-trans-retinal

ChEBI ID	CHEBI:17898

ChEBI ASCII Name	all-trans-retinal

Definition	A retinal 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:8814, CHEBI:22348, CHEBI:12776

Supplier Information	ZINC000066103386

Download	Molfile XML SDF

more structures >>

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RET - Ideal conformer

Mrv1927 07282110383D

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Time for openFile(RET - Ideal conformer

Mrv1927 07282110383D

49 49 0 0 0 0 999 V2000

-4.3270 0.9090 -0.4800 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.4660 0.1320 -1.1430 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.9980 -0.9010 -0.1420 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.9210 -1.9660 0.0750 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.6040 -1.3140 0.3800 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.3400 -0.0420 0.1310 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0510 0.4500 0.4580 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9440 -0.1450 -0.0590 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3340 0.3150 0.3000 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4460 -0.2830 -0.2200 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7200 0.1760 0.1380 C 0 0 0 0 0 0 0 0 0 0 0 0

3.8420 -0.4270 -0.3870 C 0 0 0 0 0 0 0 0 0 0 0 0

5.1150 0.0310 -0.0300 C 0 0 0 0 0 0 0 0 0 0 0 0

6.2380 -0.5730 -0.5550 C 0 0 0 0 0 0 0 0 0 0 0 0

7.5100 -0.1150 -0.1980 C 0 0 0 0 0 0 0 0 0 0 0 0

8.5000 -0.6480 -0.6610 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.6200 1.7680 -1.5310 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.8990 1.8160 0.6110 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5220 -2.1550 1.0060 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4780 1.4690 1.2590 C 0 0 0 0 0 0 0 0 0 0 0 0

5.2590 1.1850 0.9290 C 0 0 0 0 0 0 0 0 0 0 0 0

-6.2660 0.8190 -1.4190 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.0930 -0.3770 -2.0320 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.2250 -0.4110 0.8040 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.8980 -1.3680 -0.5420 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.2090 -2.6060 0.9100 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.8240 -2.5720 -0.8250 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9490 1.2980 1.1190 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0470 -0.9720 -0.7470 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3430 -1.1090 -0.9080 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8230 1.0030 0.8250 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7400 -1.2540 -1.0740 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1350 -1.4000 -1.2420 H 0 0 0 0 0 0 0 0 0 0 0 0

7.6130 0.7120 0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3510 2.4010 -2.0350 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8720 2.3940 -1.0450 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1340 1.1220 -2.2620 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.4090 1.2090 1.3590 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0890 2.3710 1.0840 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.6080 2.5160 0.1670 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9170 -3.1450 1.2340 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6860 -2.2480 0.3120 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1790 -1.6810 1.9260 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5280 1.0890 2.2790 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3910 2.0190 1.0310 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3810 2.1330 1.1600 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3090 0.8050 1.9500 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1720 1.7350 0.7010 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4000 1.8490 0.8300 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 2 0 0 0 0

15 34 1 0 0 0 0

17 35 1 0 0 0 0

17 36 1 0 0 0 0

17 37 1 0 0 0 0

18 38 1 0 0 0 0

18 39 1 0 0 0 0

18 40 1 0 0 0 0

19 41 1 0 0 0 0

19 42 1 0 0 0 0

19 43 1 0 0 0 0

20 44 1 0 0 0 0

20 45 1 0 0 0 0

20 46 1 0 0 0 0

21 47 1 0 0 0 0

21 48 1 0 0 0 0

21 49 1 0 0 0 0

M END): 18 ms

reading 49 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

49 atoms created

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

Script completed

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Wikipedia	License
Retinal (also known as retinaldehyde) is a polyene chromophore. Retinal, bound to proteins called opsins, is the chemical basis of visual phototransduction, the light-detection stage of visual perception (vision). Some microorganisms use retinal to convert light into metabolic energy. One study suggests that approximately three billion years ago, most living organisms on Earth used retinal, rather than chlorophyll, to convert sunlight into energy. Because retinal absorbs mostly green light and transmits purple light, this gave rise to the Purple Earth hypothesis. Retinal itself is considered to be a form of vitamin A when eaten by an animal. There are many forms of vitamin A, all of which are converted to retinal, which cannot be made without them. The number of different molecules that can be converted to retinal varies from species to species. Retinal was originally called retinene, and was renamed after it was discovered to be vitamin A aldehyde. Vertebrate animals ingest retinal directly from meat, or they produce retinal from carotenoids – either from α-carotene or β-carotene – both of which are carotenes. They also produce it from β-cryptoxanthin, a type of xanthophyll. These carotenoids must be obtained from plants or other photosynthetic organisms. No other carotenoids can be converted by animals to retinal. Some carnivores cannot convert any carotenoids at all. The other main forms of vitamin A – retinol and a partially active form, retinoic acid – may both be produced from retinal. Invertebrates such as insects and squid use hydroxylated forms of retinal in their visual systems, which derive from conversion from other xanthophylls.
Read full article at Wikipedia

Formula

C20H28O

Net Charge

Average Mass

284.443

Monoisotopic Mass

284.21402

InChI

InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChIKey

NCYCYZXNIZJOKI-OVSJKPMPSA-N

SMILES

[H]C(=O)\C=C(/C)\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
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.

Roles Classification
Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via retinal ) mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). gap junctional intercellular communication inhibitor An inhibitor that interferes with the process of gap junctional intercellular communication. 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-retinal (CHEBI:17898) has role gap junctional intercellular communication inhibitor (CHEBI:67195) all-trans-retinal (CHEBI:17898) has role human metabolite (CHEBI:77746) all-trans-retinal (CHEBI:17898) has role mouse metabolite (CHEBI:75771) all-trans-retinal (CHEBI:17898) is a retinal (CHEBI:15035) all-trans-retinal (CHEBI:17898) is a vitamin A (CHEBI:12777)

Incoming	(3R)-all-trans-3-hydroxyretinal (CHEBI:52228) has functional parent all-trans-retinal (CHEBI:17898) (3S)-all-trans-3-hydroxyretinal (CHEBI:52229) has functional parent all-trans-retinal (CHEBI:17898) all-trans-4-hydroxyretinal (CHEBI:139346) has functional parent all-trans-retinal (CHEBI:17898) all-trans-4-oxoretinal (CHEBI:139347) has functional parent all-trans-retinal (CHEBI:17898) N-retinylidenephosphatidylethanolamine (CHEBI:71063) has functional parent all-trans-retinal (CHEBI:17898)

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Synonyms	Sources
all-E-retinal	ChemIDplus
all-trans-retinal	KEGG COMPOUND
all-trans-retinal	UniProt
all-trans-retinaldehyde	NIST Chemistry WebBook
all-trans-retinene	KEGG COMPOUND
all-trans-vitamin A aldehyde	KEGG COMPOUND
axerophthal	MetaCyc
E-retinal	ChemIDplus
retinal	KEGG COMPOUND
retinaldehyde	ChemIDplus
retinene	KEGG COMPOUND
retinene 1	ChemIDplus
retinyl aldehyde	ChemIDplus
trans-retinal	ChemIDplus
trans-vitamin A aldehyde	HMDB
vitamin A aldehyde	KEGG COMPOUND
vitamin A1 aldehyde	ChemIDplus

Manual Xrefs	Databases
553582	ChemSpider
C00376	KEGG COMPOUND
FDB030668	FooDB
HMDB0001358	HMDB
LMPR01090002	LIPID MAPS
RET	PDBeChem
Retinal	Wikipedia
RETINAL	MetaCyc
View more database links

Registry Numbers	Types	Sources
116-31-4	CAS Registry Number	NIST Chemistry WebBook
116-31-4	CAS Registry Number	ChemIDplus
1914183	Reaxys Registry Number	Reaxys

Citations

Last Modified

28 July 2021

CHEBI:17898 - all-trans-retinal

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