3,4,5-Trimethoxycinnamic acid
PubChem CID: 735755
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| Compound Synonyms | 3,4,5-TRIMETHOXYCINNAMIC ACID, 90-50-6, 20329-98-0, O-Methylsinapic acid, 3,4,5-Trimethoxyphenylacrylic acid, 3-(3,4,5-trimethoxyphenyl)acrylic acid, (E)-3-(3,4,5-trimethoxyphenyl)acrylic acid, SINAPIC ACID METHYL ETHER, NSC 66175, 3,4,5-Trimethoxy-trans-cinnamic acid, (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid, (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid, 3-(3,4,5-Trimethoxyphenyl)-2-propenoic acid, 3,4,5-Trimethoxy cinnamic acid, 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, (2E)-, 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, Cinnamic acid, 3,4,5-trimethoxy-, EINECS 201-999-8, MFCD00004388, BRN 1537834, NSC-66175, trans-3,4,5-Trimethoxycinnamic acid, C9096D920O, Cinnamic acid, 3,4,5-trimethoxy-, (E)-, CHEBI:566519, 2-10-00-00354 (Beilstein Handbook Reference), NSC66175, (e)-3,4,5-trimethoxycinnamic acid, 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, (E)-, 3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid, SMR000371917, (2E)-3-(3,4,5-trimethoxyphenyl)acrylic acid, DTXSID7059010, O-Methylsinapate, Spectrum5_000448, bmse010224, 3,5-Trimethoxycinnamic acid, 3,4,5-Trimethoxy cinnamate, BSPBio_002796, SPECTRUM290032, MLS000757621, MLS002207275, SCHEMBL207441, CHEMBL501235, Cinnamic acid,4,5-trimethoxy-, 3,4,5-Trimethoxyphenylacrylate, DTXCID4048692, UNII-C9096D920O, MSK2650, CHEBI:228320, BDBM232204, DTXSID701298647, HMS2232E22, HMS3886I07, 3, 4, 5-Trimethoxycinnamic Acid, ALBB-007558, BBL011951, CCG-39479, s4961, STK500969, AKOS000120453, 1ST2650, 3,4,5-Trimethoxycinnamic acid, 97%, BS-4465, CS-W012839, FT71389, HY-W012123, SDCCGMLS-0066950.P001, 3,4,5-Trimethoxycinnamic acid (TMCA), NCGC00095563-01, NCGC00095563-02, 2-Propenoic acid,4,5-trimethoxyphenyl)-, AC-16693, AC-24565, AC-34784, AS-11999, DA-60204, 3-(3,4,5-Trimethoxyphenyl)propenoic acid, (E)-3-(3,4,5-trimethoxyphenyl)acrylicacid, 3,4,5-Trimethoxycinnamic acid, pred. trans, 3-(3,5-Trimethoxyphenyl)-2-propenoic acid, NS00039362, T1104, EN300-16919, (E)-3-(3,4,5-trimethoxyphenyl) acrylic acid, A10221, EN300-832999, AS-871/13102032, SR-01000773278, 3,4,5-Trimethoxycinnamic acid, predominantly trans, SR-01000773278-2, BRD-K63758740-001-02-3, Q30061098, F3284-8534, Z2315575393, 646E4CC1-F441-40D8-B1BB-87A43D1B3600, 3,4,5-Trimethoxycinnamic acid, analytical reference material, 201-999-8 |
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| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 65.0 |
| Hydrogen Bond Donor Count | 1.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | C1CCCCC1 |
| Np Classifier Class | Cinnamic acids and derivatives |
| Deep Smiles | COccc/C=C/C=O)O))))ccc6OC)))OC |
| Heavy Atom Count | 17.0 |
| Classyfire Class | Cinnamic acids and derivatives |
| Description | 3,4,5-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) [HMDB] |
| Scaffold Graph Node Level | C1CCCCC1 |
| Classyfire Subclass | Hydroxycinnamic acids and derivatives |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 262.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | Q99714, B2RXH2, P00352, P15428, Q9Y6L6, Q9NPD5, P27695, P08908, P28223, P28335, P50406, P34969, P31645, P59534, n.a. |
| Iupac Name | (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid |
| Prediction Hob | 1.0 |
| Class | Cinnamic acids and derivatives |
| Veber Rule | True |
| Classyfire Superclass | Phenylpropanoids and polyketides |
| Target Id | NPT149, NPT48, NPT94, NPT151, NPT92, NPT292 |
| Xlogp | 1.4 |
| Superclass | Phenylpropanoids and polyketides |
| Subclass | Hydroxycinnamic acids and derivatives |
| Gsk 4 400 Rule | True |
| Molecular Formula | C12H14O5 |
| Scaffold Graph Node Bond Level | c1ccccc1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | YTFVRYKNXDADBI-SNAWJCMRSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.25 |
| Logs | -3.021 |
| Rotatable Bond Count | 5.0 |
| State | Solid |
| Logd | 1.379 |
| Synonyms | 3,4,5-Trimethoxy cinnamate, 3,4,5-Trimethoxy cinnamic acid, 3,4,5-Trimethoxycinnamate, 3,4,5-Trimethoxyphenylacrylate, 3,4,5-Trimethoxyphenylacrylic acid, O-Methylsinapate, O-Methylsinapic acid, 3-(3,4,5-Trimethoxyphenyl)-2-propenoic acid, (2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoate, 3,4,5-Trimethoxycinnamic acid, 3,4,5-trimethoxycinnamate, 3,4,5-trimethoxycinnamic-acid |
| Substituent Name | Coumaric acid or derivatives, Cinnamic acid, Phenylpropene, Methoxybenzene, Styrene, Phenol ether, Anisole, Alkyl aryl ether, Benzenoid, Monocyclic benzene moiety, Monocarboxylic acid or derivatives, Ether, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aromatic homomonocyclic compound |
| Esol Class | Soluble |
| Functional Groups | c/C=C/C(=O)O, cOC |
| Compound Name | 3,4,5-Trimethoxycinnamic acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 238.084 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 238.084 |
| Hydrogen Bond Acceptor Count | 5.0 |
| Molecular Weight | 238.24 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 1.0 |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | -2.3444582705882353 |
| Inchi | 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+ |
| Smiles | COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)O |
| Nring | 1.0 |
| Np Classifier Biosynthetic Pathway | Shikimates and Phenylpropanoids |
| Defined Bond Stereocenter Count | 1.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Coumaric acids and derivatives |
| Np Classifier Superclass | Phenylpropanoids (C6-C3) |
- 1. Outgoing r'ship
FOUND_INto/from Descurainia Sophia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Erythroxylum Monogynum (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279 - 3. Outgoing r'ship
FOUND_INto/from Hansenia Forbesii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Hansenia Weberbaueriana (Plant) Rel Props:Source_db:cmaup_ingredients - 5. Outgoing r'ship
FOUND_INto/from Lepidium Apetalum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Ostericum Grosseserratum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Polygala Senega (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279 - 8. Outgoing r'ship
FOUND_INto/from Polygala Sibirica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Polygala Tenuifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all