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

ID: ALA257381

Chembl Id: CHEMBL257381

Cas Number: 514-85-2

PubChem CID: 6436082

Product Number: C135945

Max Phase: Preclinical

Molecular Formula: C20H28O

Molecular Weight: 284.44

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: 9-Cis-Retinal | Iso Rhodopsin | 9-cis-Retinal|514-85-2|9-cis-Retinaldehyde|Isoretinene A|9-cis-Vitamin A aldehyde|9-C-Retinal|Iso Rhodopsin|Retinal, 9-cis-|9-cis-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal|(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal|CHEBI:78273|EINECS 208-188-8|BRN 1914180|9-cis Retinal|cis-9-Retinal|Retinal #|(9cis)-retinal|4-07-00-01254 (Beilstein Handbook Reference)|CHEMBL257381|GTPL6673|DTXSID00891233|9-Show More

Canonical SMILES:  CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=O)C(C)(C)CCC1

Standard 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+

Standard InChI Key:  NCYCYZXNIZJOKI-MKOSUFFBSA-N

Alternative Forms

  1. Parent:

    ALA257381

    ISO RHODOPSIN

Associated Targets(Human)

AKR1B1 Tclin Aldose reductase (1404 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RHO Tbio Rhodopsin (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

RHO Rhodopsin (27 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 284.44Molecular Weight (Monoisotopic): 284.2140AlogP: 5.72#Rotatable Bonds: 5
Polar Surface Area: 17.07Molecular Species: NEUTRALHBA: 1HBD:
#RO5 Violations: 1HBA (Lipinski): 1HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 4.86CX LogD: 4.86
Aromatic Rings: Heavy Atoms: 21QED Weighted: 0.36Np Likeness Score: 2.31

References

1. Gallego O, Ruiz FX, Ardèvol A, Domínguez M, Alvarez R, de Lera AR, Rovira C, Farrés J, Fita I, Parés X..  (2007)  Structural basis for the high all-trans-retinaldehyde reductase activity of the tumor marker AKR1B10.,  104  (52): [PMID:18087047] [10.1073/pnas.0705659105]
2. Ohgane K, Dodo K, Hashimoto Y..  (2010)  Retinobenzaldehydes as proper-trafficking inducers of folding-defective P23H rhodopsin mutant responsible for retinitis pigmentosa.,  18  (19): [PMID:20805032] [10.1016/j.bmc.2010.08.014]
3. deGrip WJ, Bovee-Geurts PH, Wang Y, Verhoeven MA, Lugtenburg J..  (2011)  Cyclopropyl and isopropyl derivatives of 11-cis and 9-cis retinals at C-9 and C-13: subtle steric differences with major effects on ligand efficacy in rhodopsin.,  74  (3): [PMID:21309593] [10.1021/np100744v]

Source