Details of the Drug

General Information of Drug (ID: DMZDUXG)

Drug Name
cinnamaldehyde
Synonyms cinnamic aldehyde
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 132.16
Topological Polar Surface Area (xlogp) 1.9
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 1
ADMET Property
Elimination
After oral or intraperitoneal administration to rats and mice, 69C98% of the dose of cinnamaldehyde was recovered in the urine and feces within 24 h [2]
Chemical Identifiers
Formula
C9H8O
IUPAC Name
(E)-3-phenylprop-2-enal
Canonical SMILES
C1=CC=C(C=C1)/C=C/C=O
InChI
InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
InChIKey
KJPRLNWUNMBNBZ-QPJJXVBHSA-N
Cross-matching ID
PubChem CID
637511
ChEBI ID
CHEBI:16731
CAS Number
104-55-2
DrugBank ID
DB14184
TTD ID
D0PJ3M

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Transformation-sensitive protein p120 (TRPA1) TTELV3W TRPA1_HUMAN Activator [3]
Transient receptor potential cation channel V3 (TRPV3) TT946IA TRPV3_HUMAN Activator [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Transient receptor potential cation channel V3 (TRPV3) DTT TRPV3 7.58E-01 5.28E-03 0.05
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2423).
2 Belsito D, Bickers D, Bruze M, Calow P, Greim H, Hanifin JM, Rogers AE, Saurat JH, Sipes IG, Tagami H: A toxicologic and dermatologic assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol when used as fragrance ingredients. Food Chem Toxicol. 2007;45 Suppl 1:S1-23. doi: 10.1016/j.fct.2007.09.087. Epub 2007 Sep 18.
3 Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57.
4 More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43.
5 Pharmacological profiling of the TRPV3 channel in recombinant and native assays. Br J Pharmacol. 2014 May;171(10):2631-44.
6 2-aminoethoxydiphenyl borate activates and sensitizes the heat-gated ion channel TRPV3. J Neurosci. 2004 Jun 2;24(22):5177-82.
7 Biphasic currents evoked by chemical or thermal activation of the heat-gated ion channel, TRPV3. J Biol Chem. 2005 Apr 22;280(16):15928-41.
8 Citral sensing by Transient [corrected] receptor potential channels in dorsal root ganglion neurons. PLoS One. 2008 May 7;3(5):e2082.
9 17(R)-resolvin D1 specifically inhibits transient receptor potential ion channel vanilloid 3 leading to peripheral antinociception. Br J Pharmacol. 2012 Feb;165(3):683-92.
10 Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels. Nat Neurosci. 2006 May;9(5):628-35.
11 Monoterpenoid agonists of TRPV3. Br J Pharmacol. 2007 Jun;151(4):530-40.
12 Cannabinoid actions at TRPV channels: effects on TRPV3 and TRPV4 and their potential relevance to gastrointestinal inflammation. Acta Physiol (Oxf). 2012 Feb;204(2):255-66.
13 TRPV1-mediated itch in seasonal allergic rhinitis. Allergy. 2009 May;64(5):807-10.
14 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
15 NPPB structure-specifically activates TRPA1 channels. Biochem Pharmacol. 2010 Jul 1;80(1):113-21.
16 Transient receptor potential A1 mediates acetaldehyde-evoked pain sensation. Eur J Neurosci. 2007 Nov;26(9):2516-23.
17 Resolvin D1 attenuates activation of sensory transient receptor potential channels leading to multiple anti-nociception. Br J Pharmacol. 2010 Oct;161(3):707-20.
18 An ion channel essential for sensing chemical damage. J Neurosci. 2007 Oct 17;27(42):11412-5.
19 ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29.
20 Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress. J Neurosci. 2008 Mar 5;28(10):2485-94.
21 TRPA1 and TRPV1 activation is a novel adjuvant effect mechanism in contact hypersensitivity. J Neuroimmunol. 2009 Feb 15;207(1-2):66-74.
22 Cox-dependent fatty acid metabolites cause pain through activation of the irritant receptor TRPA1. Proc Natl Acad Sci U S A. 2008 Aug 19;105(33):12045-50.