Sinapic acid

  • GreenMolBD CID : 2833
  • Molecular Formula : C11H12O5
  • Molecular Weight : 224.212
  • Exact Molecular Mass : 224.068
  • IUPAC Name : (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
  • InChI : InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
  • InChI Key : PCMORTLOPMLEFB-ONEGZZNKSA-N
  • Canonical SMILES : COC1=CC(=CC(=C1O)OC)C=CC(=O)O
  • Isomeric SMILES : COc1cc(cc(c1O)OC)/C=C/C(=O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

1.3. Alternative Parent

Coumaric acids and derivatives; Cinnamic acids; Methoxyphenols; Dimethoxybenzenes; Styrenes; Phenoxy compounds; Anisoles; Alkyl aryl ethers; Monocarboxylic acids and derivatives; Carboxylic acids; Organic oxides; Hydrocarbon derivatives; Carbonyl compounds;

1.4. Molecular Framework

Aromatic homomonocyclic compounds

1.5. Substituents

Cinnamic acid; Coumaric acid or derivatives; Hydroxycinnamic acid; M-dimethoxybenzene; Dimethoxybenzene; Methoxyphenol; Phenoxy compound; Anisole; Methoxybenzene; Styrene; Phenol ether; Alkyl aryl ether; Phenol; 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

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
1.5072 75.99 2 5 16 4 6 6 5.78806 284.66 238.719 0.787648

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-170.635826 0.68 -4.745 -8.69392 -0.79641 3.949

4. Compound Reactivity

DLP nRFG nLMR
0 1 3

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Toxic 1.19351 3254.56 0.0511262 None Strong Mild Degradable 0.0075719 6.90945

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes Yes Yes Yes Yes Yes

7. Synonyms

Name
SINAPIC ACID
3,5-Dimethoxy-4-hydroxycinnamic acid
Sinapinic acid
530-59-6
SINAPINATE
Sinapate
4-Hydroxy-3,5-dimethoxycinnamic acid
Synapoic acid
trans-sinapic acid
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
UNII-P0I60993EC
7362-37-0
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylic acid
3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
2-Propenoic acid, 3-(4-hydroxy-3,5-dimethoxyphenyl)-
CHEMBL109341
3,5-dimethoxy-4-hydroxy-trans-cinnamic acid
CHEBI:15714
PCMORTLOPMLEFB-ONEGZZNKSA-N
P0I60993EC
Cinnamic acid, 4-hydroxy-3,5-dimethoxy-, (E)-
NSC59261
(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylic acid
MFCD00004401
4-Hydroxy-3,5-dimethoxy-cinnamic acid
AK-29344
2-Propenoic acid, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (E)-
trans-3,5-Dimethoxy-4-hydroxycinnamic acid
SXX
W-105777
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid
3-(4-hydroxy-3,5-dimethoxyphenyl)-(E)-2-propenoic acid
2-propenoic acid, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-
3-(4-hydroxy-3,5-dimethoxyphenyl)acrylic acid
(E)-Sinapic acid
Sinapic acid, trans-
3,5-DIMETHOXY-4-HYDROXY CINNAMIC ACID
AC1LCUXW
bmse000318
bmse000594
bmse010209
AC1Q47EG
SCHEMBL37312
MLS001066354
Sinapic acid, >=98%, powder
STOCK1N-17013
CHEBI:77131
BIS8112
MolPort-000-154-620
MolPort-019-904-823
ZX-AFC000604
HMS2230P08
ZINC153654
ZX-AT021035
4-Hydroxy-3,5-dimethoxycinnamicacid
BDBM50341142
NSC-59261
OR1178
SBB061895
AKOS015851820
3, 5-dimethoxy-4-hydroxycinnamic acid
CCG-214595
CD-1325
DB08587
MS-8962
RP27516
RTX-012048
trans-Sinapic acid, analytical standard
NCGC00247028-01
AJ-13047
AK500433
AN-45615
OR005400
OR138104
OR279185
SC-13259
SMR000471879
ST098710
SY018287
Cinnamic acid, 4-hydroxy-3,5-dimethoxy-
SBI-0206696.P002
3,5-DIMETHOXY-4-HYDROXYCINNAMICACID
AB0020603
AB1009201
KB-179658
4-Hydroxy-3,5-dimethoxy-(E)-Cinnamic acid
ST24041243
V1546
EN300-93177
C00482
J10227
K-9641
3-(4-hydroxy-3,5-dimethoxy-phenyl)-acrylic acid
I01-5955
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-Propenoic acid
(E)-3-(4-Hydroxy-3,5-dimethoxy-phenyl)-acrylic acid
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid #
(E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)prop-2-enoic acid
(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(2E)-2-Propenoic acid
4-Hydroxy-3,5-dimethoxycinnamic Acid, Predominantly trans
7AE78999-D500-492B-9651-46622E8DAA71
Sinapic acid, matrix substance for MALDI-MS, >=99.0% (T)
UNII-68A28V6010 component PCMORTLOPMLEFB-ONEGZZNKSA-N
Sinapic acid, matrix substance for MALDI-MS, >=99.5%, Ultra pure
InChI=1/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Sinapic acid
Ichnocarpus frutescens Leaf 8
Juglans regia Fruit 6 , 17
Phaseolus vulgaris Seed 1 , 2

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
112 Cyclooxygenase Homo sapiens 1WB4,4Q8B 28000 10.1016/j.bmcl.2012.02.002 22386242
113 Cyclooxygenase-1 (COX-1) 1WB4,4Q8B 39200 10.1016/j.bmcl.2012.02.002 22386242
43 glutaminase GLS Homo sapiens 15.8489 624170
678 sphingomyelin phosphodiesterase 1 SMPD1 Homo sapiens 25.1189 504937
78 Tyrosinase Agaricus bisporus >351000 10.1016/j.bmcl.2011.02.028 21377874

10. Chemical Vendors

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293113327Aurora Fine Chemicals LLCSource URLSource DetailA02.235.835Source Record URL
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