Showing Compound all-trans-retinal (FDB030668)

Record Information

Version

1.0

Creation date

2015-05-07 19:45:12 UTC

Update date

2019-11-26 03:21:51 UTC

Primary ID

FDB030668

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

all-trans-retinal

Description

13-cis-retinal, also known as vitamin a aldehyde or retinaldehyde, is a member of the class of compounds known as retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Thus, 13-cis-retinal is considered to be an isoprenoid lipid molecule. 13-cis-retinal is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 13-cis-retinal can be found primarily in blood, as well as throughout most human tissues. Within the cell, 13-cis-retinal is primarily located in the cytoplasm and in the membrane (predicted from logP). It can also be found in the extracellular space. 13-cis-retinal exists in all living organisms, ranging from bacteria to humans. In humans, 13-cis-retinal is involved in the retinol metabolism. 13-cis-retinal is also involved in vitamin A deficiency, which is a metabolic disorder.

CAS Number

116-31-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
11 cis Retinal	HMDB
11-cis-Retinal	HMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal	HMDB
Aldehyde, vitamin a	HMDB
all-e-Retinal	HMDB
all-epsilon-Retinal	HMDB
all-trans-Retinal	Kegg
all-trans-Retinaldehyde	ChEBI
all-trans-Retinene	ChEBI
all-trans-Vitamin a aldehyde	ChEBI

Showing 1 to 10 of 21 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	6.62	ALOGPS
logP	4.86	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.87 m³·mol⁻¹	ChemAxon
Polarizability	35.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H28O

IUPAC name

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

InChI Identifier

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+

InChI Key

NCYCYZXNIZJOKI-OVSJKPMPSA-N

Isomeric SMILES

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

Average Molecular Weight

284.4357

Monoisotopic Molecular Weight

284.214015518

Classification

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoid skeleton
Diterpenoid
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinal (CHEBI:17898 )
Retinoids (C00376 )
Retinoids (LMPR01090002 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Retinal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2290000000-df9d2aa7545cc60a54f9	Spectrum
Predicted GC-MS	Retinal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9700000000-c2e22000dfae0765c367	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03g0-0950000000-bccf87de037f98873f41	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-1910000000-5fe7643c395769c68286	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9700000000-fca532f917595376d653	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0490000000-f543f08fbaf94a2e3f8e	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3940000000-74f087cc812b3715e7ac	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fri-9830000000-72a5d01c6181340ad986	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-bad35938b77f181c29b9	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-1aadad0770df07f98436	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ko-4690000000-f624d342f88456375b9c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00n3-1960000000-43f8c66f164764c37361	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0609-3920000000-dbeab0a82b306761cf6a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-7900000000-d2bb7c1aeeb87d8833d2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a59-0090000000-2ec2f8f314943441fa15	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-0190000000-312cebb17ccd0189ab4d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1590000000-b2551eac481c0c930a4d	2021-09-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

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Old DFC IDS

Not Available

Associated Foods

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

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Metabolism

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Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Files

MSDS

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References

Synthesis Reference

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General Reference

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Content Reference

Showing Compound all-trans-retinal (FDB030668)

Structure for FDB030668 (all-trans-retinal)