Showing Compound Card for Safranal (CDB000084)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (2) Show 7 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:24:10 UTC
Updated at2020-12-07 19:07:04 UTC
CannabisDB IDCDB000084
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSafranal
DescriptionSafranal belongs to the class of organic compounds known as organic oxides which contain an oxide group. Safranal is a neutral compound. Safranal is a component of saffron (PMID: 28705037 ), the spice made from drying the stigmas and styles of crocus flowers (Crocus sativus). Safranal, the constituent primarily responsible for the aroma of saffron, has a sweet, fresh, and herbal taste and is a flavouring ingredient. Safranal has been detected in cauliflowers, cumin seeds, elderberry, figs, lemon, rooibos, saffrons, wolfberry, and tea leaf making safranal a potential biomarker for the consumption of these foods. Safranal is found in cannabis plants (PMID:6991645 ). Safranal is an effective anticonvulsant (PMID: 29609687 ) shown to act as an agonist at the gamma aminobutyric acid (GABA)A-benzodiazepine receptor complex (PMID: 16707256 ). Safranal also exhibits high antioxidant and free radical scavenging activity (PMID: 16317646 ), along with cytotoxicity towards cancer cells in vitro (PMID: 8620447 ). It has also been shown to have antidepressant properties (PMID: 15341662 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2,6,6-Trimethylcyclohexa-1,3-dienyl)methanalChEBI
1,1,3-Trimethyl-2-formylcyclohexa-2,4-dieneChEBI
2,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehydeChEBI
2,6,6-Trimethylcyclohexa-1,3-dienyl methanalChEBI
Dehydro-beta-cyclocitralChEBI
Dehydro-b-cyclocitralGenerator
Dehydro-β-cyclocitralGenerator
1-Formyl-2,6,6-trimethyl-1,3-cyclohexadieneHMDB
2,3-dihydro-2,2,6-TrimethylbenzaldehydeHMDB
2,6,6-Trimethyl-1,3-cyclohexadienalHMDB
2,6,6-Trimethyl-1,3-cyclohexadiene-1-carbaldehydeHMDB
2,6,6-Trimethyl-1,3-cyclohexadienecarboxaldehyde, 9ciHMDB
FEMA 3389HMDB
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde
Traditional Namesafranal
CAS Registry Number116-26-7
SMILES
CC1=C(C=O)C(C)(C)CC=C1
InChI Identifier
InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3
InChI KeySGAWOGXMMPSZPB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxides
Sub ClassNot Available
Direct ParentOrganic oxides
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point70 °C at 1 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.93ALOGPS
logP2.05ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.22 m³·mol⁻¹ChemAxon
Polarizability17.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSafranal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kg9-2900000000-b082ebe4ee4447dc7980Spectrum
Predicted GC-MSSafranal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSafranal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-b34ca14deaad2e3be8c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-9700000000-317a87cd8595a79b42d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-2993b4b7b24364148faf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e83c23e4fe0dedd738e72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-648f823a03c6712751e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ng-8900000000-b0e87ace4983e8eca5152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b7cb4601ae2fb08997c12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-0900000000-449dca9897e0f32093242021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-861947f0491f909a25882021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-4900000000-f591f9acd9c148c93dd02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9800000000-066e7f2d59fb906577f82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-9300000000-c8eb85059ddf025ee54a2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Gamma-aminobutyric acid receptor subunit alpha-2GABRA24p12P47869 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Gamma-aminobutyric acid type B receptor subunit 1GABBR16p21.31Q9UBS5 details
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Gamma-aminobutyric acid receptor subunit alpha-2GABRA24p12P47869 details
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0036061
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014884
KNApSAcK IDC00035737
Chemspider ID55000
KEGG Compound IDC17062
BioCyc IDCPD-8669
BiGG IDNot Available
Wikipedia LinkSafranal
METLIN IDNot Available
PubChem Compound61041
PDB IDNot Available
ChEBI ID53169
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Rameshrad M, Razavi BM, Hosseinzadeh H: Saffron and its derivatives, crocin, crocetin and safranal: a patent review. Expert Opin Ther Pat. 2018 Feb;28(2):147-165. doi: 10.1080/13543776.2017.1355909. Epub 2017 Jul 18. [PubMed:28705037 ]
  3. Bo-Qiang L, Si-Tong Z, Zu-Yuan L, Wan-Yun N, Bin C, Yuan L, Xuyun L, Liangen M, You-Chao C, Xin-Zhen Y, Zhong C, Xiao-Ying Y, Wei-Wei H: Safranal carried by nanostructured lipid vehicles inhibits generalized epilepsy in mice. Pharmazie. 2018 Apr 2;73(4):207-212. doi: 10.1691/ph.2018.7310. [PubMed:29609687 ]
  4. Hosseinzadeh H, Sadeghnia HR: Protective effect of safranal on pentylenetetrazol-induced seizures in the rat: involvement of GABAergic and opioids systems. Phytomedicine. 2007 Apr;14(4):256-62. doi: 10.1016/j.phymed.2006.03.007. Epub 2006 May 16. [PubMed:16707256 ]
  5. Assimopoulou AN, Sinakos Z, Papageorgiou VP: Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents. Phytother Res. 2005 Nov;19(11):997-1000. doi: 10.1002/ptr.1749. [PubMed:16317646 ]
  6. Escribano J, Alonso GL, Coca-Prados M, Fernandez JA: Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro. Cancer Lett. 1996 Feb 27;100(1-2):23-30. doi: 10.1016/0304-3835(95)04067-6. [PubMed:8620447 ]
  7. Akhondzadeh S, Fallah-Pour H, Afkham K, Jamshidi AH, Khalighi-Cigaroudi F: Comparison of Crocus sativus L. and imipramine in the treatment of mild to moderate depression: a pilot double-blind randomized trial [ISRCTN45683816]. BMC Complement Altern Med. 2004 Sep 2;4:12. doi: 10.1186/1472-6882-4-12. [PubMed:15341662 ]

Transporters

Enzyme Details
1. Gamma-aminobutyric acid receptor subunit alpha-1
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
Enzyme Details
2. Gamma-aminobutyric acid receptor subunit alpha-2
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular weight:
51325.9