CAS 514-85-2|(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal|9-顺式视黄醛|9-cis-retinal|维生素 A 醛|9-cis-Retinal|Isoretinene a|9-cis-Retinaldehyde|9-cis-Vitam...

General Information

Structure

Molecular Formula

C₂₀H₂₈O

Molecular Mass

284.43572

Exact Mass

284.21401552

Charge

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-MKOSUFFBSA-N

Canonic Smiles

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

Isomeric Smiles

CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C=O)\C)/C

Calculated Properties

JChem

LogD (pH = 7.4)

4.86

LogD (pH = 5.5)

4.86

Log P

4.86

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-4.06

Polar Surface Area

17.07

Polarizability

35.03

Molar Refractivity

96.87

LOG S

-6.99

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC name

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

IUPAC Traditional name

9-cis-retinal tocopherol, α

Synonyms

9-顺式视黄醛维生素 A 醛9-cis-RetinalIsoretinene a9-cis-Retinaldehyde9-cis-Vitamin A Aldehyde9-Z-Retinal9-cis-Retinalisoretinene A9-cis-7,11,13-trans-retinal9-C-retinal9-cis-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal9-cis-retinal(9cis)-retinal9-cis-retinaldehyde(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal9-cis-vitamin A aldehyde9-cis-retinal

Names and Identifiers

Registration numbers

PubChem SID

24899382162228582223443640

CAS Number

MDL Number

EC Number

PubChem CID

BRENDA Ligand Database

131432897

BRENDA Database

1.2.3.11.1.1.11.1.1.1051.1.1.21.2.1.31.1.1.3001.13.11.631.1.1.1841.2.1.361.1.1.315

Reactom Database

R-HSA-5696101

SABIO-RK Database

101836784803913600

MetaboLights Database

MTBLS2406MTBLS1411MTBLS4820MTBLS334MTBLS1622

MetaCyc Database

CPD-13536

PubMed Citation Links

2209031320837787475042517003450118826551038963710064560

BKMS React Database

131432897

Rhea Database

RHEA:54916RHEA:42084RHEA:42052RHEA:65524

KEGG ID

CHEBI ID

CompTox Database

LIPID MAPS Instance

CHEMBL

HMDB Database

Reaxys Registry

SureChEMBL Database

Registration numbers

Properties

Product Information

Shipped in

dry ice

Certificate of Analysis

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

TRC

R239850

9-cis-Retinal is an isomer of all-trans-Retinal (R240000).

Sigma Aldrich

R5754

Biochem/physiol Actions
Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.9-cis retinal is a natural ligand (chromophore) of the vertebrate rod visual pigment. 9-cis retinal is used in studies on the mechanisms of visual function.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R5754.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

ChEBI

CHEBI:78273

A retinal in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration.

Molecule Details

References

PubChem Literature

From Data Sources

• Yan, E., et al.: Biochemistry, 43, 10867 (2004)

• Kukura, P., et al.: Science, 310, 1006 (2004)

• Ridge, K., et al.: J. Biol. Chem., 282, 9297 (2004)

References

Bioactivity