3,4-Dimethoxycinnamic acid

Details

• Internal ID: 8a86d5ec-d858-4ff2-b691-064688dbf229
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC(=O)O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C(=O)O)OC
• InChI: InChI=1S/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13)/b6-4+
• InChI Key: HJBWJAPEBGSQPR-GQCTYLIASA-N
• Popularity: 195 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21 g/mol
• Exact Mass: 208.07355886 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 2316-26-9
• 14737-89-4
• Dimethylcaffeic acid
• (E)-3-(3,4-dimethoxyphenyl)acrylic acid
• Caffeic acid dimethyl ether
• (E)-3,4-dimethoxycinnamic acid
• o-Methylferulic acid
• 3,4-Dimethoxycinnamic acid, predominantly trans
• (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid
• Dimethyl caffeic acid
• 3-(3,4-Dimethoxyphenyl)-2-propenoic Acid
• 3-(3,4-Dimethoxyphenyl)propenoic acid
• (E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid
• 3,4-Dimethoxycinnamicacid
• (2E)-3-(3,4-dimethoxyphenyl)acrylic acid
• 2-Propenoic acid, 3-(3,4-dimethoxyphenyl)-, (2E)-
• (E)-3',4'-Dimethoxycinnamic acid
• 3,4-Dimethoxycinnamic acid, (E)-
• UNII-BVZ841PVJL
• MFCD00004387
• BVZ841PVJL
• 3,4-Dimethoxyphenyl-2-propenoic acid
• 3-(3,4-dimethoxyphenyl)acrylic acid
• 3, 4-Dimethoxycinnamic acid
• CHEMBL320295
• CHEBI:86549
• NSC4323
• (e)-3-(3,4-dimethoxyphenyl)-2-propenoic acid
• 3,4-dimethoxy-trans-cinnamic acid
• NSC-4323
• EINECS 238-801-4
• NSC-43569
• Cinnamic acid,4-dimethoxy-
• (2E)-3-(3,4-Dimethoxyphenyl)-2-propenoic acid
• 2-Propenoic acid, 3-(3,4-dimethoxyphenyl)-, (E)-
• (E)-O-Methylferulic acid
• trans-3,4-Dimethoxycinnamic acid
• 2-Propenoic acid,4-dimethoxyphenyl)-
• SMR000112198
• 2-Propenoic acid, 3-(3,4-dimethoxyphenyl)-
• Cinnamic acid, 3,4-dimethoxy-
• NSC 4323
• EINECS 219-025-5
• NSC 43569
• 3-(3,4-dimethoxy-phenyl)-acrylic acid
• 1185241-38-6
• AI3-24427
• Spectrum5_000142
• bmse010210
• O,O'-Dimethylcaffeic Acid
• 3,4-dimethoxy-cinnamic acid
• SCHEMBL81317
• BSPBio_001672
• SPECTRUM210567
• MLS000570053
• MLS002695959
• BIDD:ER0423
• SPECTRUM1505130
• 3',4'-dimethoxycinnamic acid
• E)-3,4-Dimethoxycinnamic acid
• 3,4-Dimethoxybenzeneacrylic acid
• 3,4-Dimethoxycinnamic acid, 8CI
• DTXSID501016475
• HMS2268F17
• AMY32184
• HY-N1778
• NSC43569
• AC7547
• BBL009859
• BDBM50341141
• CCG-38678
• s9341
• STK298625
• AKOS000119628
• AC-8314
• CS-W020726
• SDCCGMLS-0066525.P001
• NCGC00095522-01
• NCGC00095522-02
• NCGC00095522-03
• NCGC00095522-06
• D1728
• (E)-3-(3,4-Dimethoxy-phenyl)-acrylic acid
• EN300-16808
• A21728
• CINNAMIC ACID, 3,4-DIMETHOXY-, (E)-
• EN300-367322
• 3-(3,4-Dimethoxyphenyl)-(E)-2-Propenoic acid
• 3,4-Dimethoxycinnamic acid (O-Methylferulic acid)
• 3-(3,4-Dimethoxyphenyl)-2-propenoic acid, 9CI
• 7R-0613
• A884433
• SR-01000712420
• 2-Propenoic acid,3-(3,4-dimethoxyphenyl)-,(2E)-
• 2-Propenoic acid,3-(3,4-dimethoxyphenyl)-,(E)-
• J-010506
• SR-01000712420-2
• W-107420
• (2E)-(3,4-DIMETHOXYPHENYL)-2-PROPENOIC ACID
• 3,4-Dimethoxycinnamic acid, predominantly trans, 99%
• BRD-K96256403-001-05-0
• Q15410159
• 49C7DB89-C3D8-411B-B043-A8335FDDD98E
• F3095-1806
• TRANS-3-(3,4-DIMETHOXYPHENYL)-2-PROPENOIC ACID
• Z2573653932
• InChI=1/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13)/b6-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.8672	86.72%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8623	86.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9550	95.50%
OATP1B3 inhibitior	+	0.9798	97.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7411	74.11%
P-glycoprotein inhibitior	-	0.9827	98.27%
P-glycoprotein substrate	-	0.9502	95.02%
CYP3A4 substrate	-	0.6619	66.19%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8567	85.67%
CYP3A4 inhibition	-	0.8604	86.04%
CYP2C9 inhibition	-	0.9282	92.82%
CYP2C19 inhibition	-	0.8081	80.81%
CYP2D6 inhibition	-	0.9417	94.17%
CYP1A2 inhibition	-	0.8629	86.29%
CYP2C8 inhibition	+	0.5267	52.67%
CYP inhibitory promiscuity	-	0.8081	80.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7197	71.97%
Carcinogenicity (trinary)	Non-required	0.6339	63.39%
Eye corrosion	+	0.4560	45.60%
Eye irritation	+	0.9716	97.16%
Skin irritation	+	0.7105	71.05%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6263	62.63%
Micronuclear	+	0.5507	55.07%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8309	83.09%
Respiratory toxicity	-	0.9111	91.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.7461	74.61%
Acute Oral Toxicity (c)	III	0.6244	62.44%
Estrogen receptor binding	+	0.5624	56.24%
Androgen receptor binding	+	0.6652	66.52%
Thyroid receptor binding	-	0.7050	70.50%
Glucocorticoid receptor binding	-	0.7530	75.30%
Aromatase binding	-	0.6244	62.44%
PPAR gamma	-	0.7912	79.12%
Honey bee toxicity	-	0.9562	95.62%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6207	62.07%
Fish aquatic toxicity	+	0.9647	96.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	22387.2 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM; 35481.3 nM; 28183.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	446.7 nM; 446.7 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.34%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.07%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.42%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.20%	95.56%
CHEMBL1255126	O15151	Protein Mdm4	86.68%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.11%	99.17%
CHEMBL3194	P02766	Transthyretin	85.74%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.61%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.96%	91.11%
CHEMBL4208	P20618	Proteasome component C5	83.76%	90.00%
CHEMBL2535	P11166	Glucose transporter	82.51%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.76%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.74%	89.62%

Plants that contains it

• Acorus calamus
• Acorus calamus var. angustatus
• Acorus gramineus
• Actaea simplex
• Anodendron affine
• Bacopa monnieri
• Buddleja asiatica
• Cedrela salvadorensis
• Chrysosplenium americanum
• Eriocapitella tomentosa
• Eritrichium sericeum
• Euphorbia tithymaloides
• Galium latoramosum
• Garcinia gummi-gutta
• Hertia cheirifolia
• Laggera alata
• Licaria chrysophylla
• Olea europaea
• Ormosia hosiei
• Ornithoglossum viride
• Petasites radiatus
• Phlogacanthus tubiflorus
• Phlomoides rotata
• Polygala tenuifolia
• Populus nigra
• Rugelia nudicaulis
• Sabia japonica
• Schizanthus tricolor
• Selenicereus undatus
• Sibiraea angustata
• Sphaeranthus confertifolius
• Verbesina gigantea
• Woodsia manchuriensis

Cross-Links

• PubChem: 717531
• NPASS: NPC294941
• ChEMBL: CHEMBL320295
• LOTUS: LTS0059066
• wikiData: Q15410159