You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 14:17:55 UTC
Update Date2017-03-02 21:27:03 UTC
HMDB IDHMDB02511
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,4,5-Trimethoxycinnamic acid
Description3,4,5-Trimethoxycinnamic acid is an organic acid found in normal human urine. (PMID: 6992730 , 6511847 ). Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID: 16313198 ).
Structure
Thumb
Synonyms
ValueSource
3,4,5-Trimethoxy cinnamateHMDB
3,4,5-Trimethoxy cinnamic acidHMDB
3,4,5-TrimethoxycinnamateHMDB
3,4,5-TrimethoxyphenylacrylateHMDB
3,4,5-Trimethoxyphenylacrylic acidHMDB
O-MethylsinapateHMDB
O-Methylsinapic acidHMDB
Chemical FormulaC12H14O5
Average Molecular Weight238.2366
Monoisotopic Molecular Weight238.084123558
IUPAC Name(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
Traditional Name3,4,5-trimethoxycinnamic acid
CAS Registry Number90-50-6
SMILES
COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC
InChI Identifier
InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+
InChI KeyYTFVRYKNXDADBI-SNAWJCMRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point126 - 128 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 mg/mLALOGPS
logP2.24ALOGPS
logP1.66ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.71ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.45 m3·mol-1ChemAxon
Polarizability24.17 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0019-5980000000-481902850188a4b983e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0890000000-73d378c5d062a4380537View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014r-0900000000-7d415b23b8c22936e972View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b27641d2926e1d3e69edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0190000000-a53a43c16d61d22ba5fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-0970000000-e99d426adbbcf08b402bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ox-0910000000-eb35950d925bbd52e2e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c166d05b1d38a4369d13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-8e02e6181e389f2fce58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-b96acc7d851ea2cbe471View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c690fb44764739147531View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0690000000-37f50a89d80a7d8e7b7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0790000000-a0f7d5eacf28002d6c1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0590000000-5e15df23e1760f95e514View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0490000000-528be5b0367f05c60956View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-2900000000-a43198a76493a4d0f488View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01vo-0920000000-f5f28fbcb7e0a5bb9b80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0950000000-6278f1b12421863b19afView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.046 +/- 0.009 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023019
KNApSAcK IDNot Available
Chemspider ID642910
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02511
Metagene LinkHMDB02511
METLIN ID6705
PubChem Compound735755
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72. [PubMed:15721987 ]
  2. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]
  3. Kissling E: [The detection of Azotobacter and its significance in criminal technical soil examinations]. Arch Kriminol. 1980;165(1-2):27-34. [PubMed:6992730 ]
  4. Kumar S, Arya P, Mukherjee C, Singh BK, Singh N, Parmar VS, Prasad AK, Ghosh B: Novel aromatic ester from Piper longum and its analogues inhibit expression of cell adhesion molecules on endothelial cells. Biochemistry. 2005 Dec 6;44(48):15944-52. [PubMed:16313198 ]