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	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

RET - Ideal conformer

Mrv1927 07282110383D

starting HoverWatcher_5

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): 31 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

Jmol script terminated

Molfile expand

Wikipedia	License
γ-Butyrolactone (GBL) or gamma-butyrolactone is an organic compound with the formula O=CO(CH2)3. It is a hygroscopic, colorless, water-miscible liquid with a weak characteristic odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone. In humans, GBL acts as a prodrug for gamma-hydroxybutyric acid (GHB) and is often used as a recreational drug. GHB acts as a central nervous system (CNS) depressant with effects similar to those of barbiturates.
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	Types	Sources
12168520	PubMed citation	Europe PMC
15500295	PubMed citation	Europe PMC
15686550	PubMed citation	Europe PMC
15724104	PubMed citation	Europe PMC
16004575	PubMed citation	Europe PMC
16054134	PubMed citation	Europe PMC
16128572	PubMed citation	Europe PMC
17326003	PubMed citation	Europe PMC
21447403	PubMed citation	Europe PMC
21995425	PubMed citation	Europe PMC
22162152	PubMed citation	Europe PMC
22198730	PubMed citation	Europe PMC
22220722	PubMed citation	Europe PMC
22417174	PubMed citation	Europe PMC
22428905	PubMed citation	Europe PMC
22431612	PubMed citation	Europe PMC
22515697	PubMed citation	Europe PMC
22529810	PubMed citation	Europe PMC
22559266	PubMed citation	Europe PMC
22621924	PubMed citation	Europe PMC
22841964	PubMed citation	Europe PMC
22879987	PubMed citation	Europe PMC
26568132	PubMed citation	Europe PMC
28780307	PubMed citation	Europe PMC
31931077	PubMed citation	Europe PMC
32212312	PubMed citation	Europe PMC
32371567	PubMed citation	Europe PMC
32492112	PubMed citation	Europe PMC
33034385	PubMed citation	Europe PMC
33334878	PubMed citation	Europe PMC

Last Modified

28 July 2021

CHEBI:17898 - all-trans-retinal

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