3-(3,4,5-Trimethoxyphenyl)propanoic acid

Details

• Internal ID: a89c50f9-d219-48de-add4-b2c3e53168bf
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: 3-(3,4,5-trimethoxyphenyl)propanoic acid
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)CCC(=O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)CCC(=O)O
• InChI: InChI=1S/C12H16O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h6-7H,4-5H2,1-3H3,(H,13,14)
• InChI Key: ZCYXGVJUZBKJAI-UHFFFAOYSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.25 g/mol
• Exact Mass: 240.09977361 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 3-(3,4,5-Trimethoxyphenyl)propanoic acid
• 3-(3,4,5-Trimethoxyphenyl)propionic acid
• Benzenepropanoic acid, 3,4,5-trimethoxy-
• 3,4,5-trimethoxydihydrocinnamic acid
• 3,4,5-Trimethoxyhydrocinnamic acid
• 3,4,5-Trimethoxyphenylpropionic acid
• CHEBI:583580
• MFCD00002775
• 3,4,5-trimethoxy-benzenepropanoic acid
• 3,4,5-Trimethoxybenzenepropanoic acid
• EINECS 246-706-4
• NSC169988
• NSC 169988
• AI3-38431
• Maybridge1_005958
• Oprea1_083965
• SCHEMBL429622
• CHEMBL484645
• MEGxp0_002067
• ACon1_001226
• HMS558G18
• DTXSID60179842
• CCG-52269
• AKOS000119417
• DS-6653
• HY-W022390
• NSC-169988
• Benzenepropanoic acid,3,4,5-trimethoxy-
• NCGC00169556-01
• 3-(3,4,5-Trimethoxyphenyl)propionicacid
• PD099450
• SY109418
• 3-(3,4,5-trimethoxyphenyl) propionic acid
• CS-0041622
• FT-0613601
• 3-(3,4,5-Trimethoxy-phenyl)-propionic acid
• beta-(3,4,5-Trimethoxy phenyl)propionic acid
• EN300-17346
• 3-(3',4',5'-trimethoxyphenyl)propionic acid
• beta -(3,4,5-Trimethoxy phenyl)propionic acid
• D78077
• .beta.-(3,4,5-Trimethoxy phenyl)propionic acid
• A817683
• 3-(3,4,5-Trimethoxyphenyl)propionic acid, >=98%
• J-015850
• SR-01000641513-1
• BRD-K95734889-001-01-9
• Q27225779
• Z56922108
• NCGC00169556-02!3-(3,4,5-trimethoxyphenyl)propanoic acid
• InChI=1/C12H16O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h6-7H,4-5H2,1-3H3,(H,13,14

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9824	98.24%
Caco-2	+	0.8987	89.87%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8803	88.03%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.9259	92.59%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7866	78.66%
P-glycoprotein inhibitior	-	0.9632	96.32%
P-glycoprotein substrate	-	0.9358	93.58%
CYP3A4 substrate	-	0.5898	58.98%
CYP2C9 substrate	+	0.5512	55.12%
CYP2D6 substrate	-	0.7906	79.06%
CYP3A4 inhibition	-	0.9594	95.94%
CYP2C9 inhibition	-	0.9637	96.37%
CYP2C19 inhibition	-	0.8788	87.88%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.8494	84.94%
CYP2C8 inhibition	+	0.5564	55.64%
CYP inhibitory promiscuity	-	0.9463	94.63%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7715	77.15%
Carcinogenicity (trinary)	Non-required	0.7281	72.81%
Eye corrosion	-	0.9255	92.55%
Eye irritation	+	0.9162	91.62%
Skin irritation	-	0.6004	60.04%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4760	47.60%
Micronuclear	-	0.6908	69.08%
Hepatotoxicity	-	0.6305	63.05%
skin sensitisation	-	0.8461	84.61%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.8870	88.70%
Acute Oral Toxicity (c)	III	0.6719	67.19%
Estrogen receptor binding	-	0.6813	68.13%
Androgen receptor binding	-	0.8239	82.39%
Thyroid receptor binding	-	0.5994	59.94%
Glucocorticoid receptor binding	-	0.7244	72.44%
Aromatase binding	-	0.7558	75.58%
PPAR gamma	-	0.7536	75.36%
Honey bee toxicity	-	0.9506	95.06%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7904	79.04%
Fish aquatic toxicity	+	0.6545	65.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.63%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.36%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	93.35%	90.20%
CHEMBL2581	P07339	Cathepsin D	93.19%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.83%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.19%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.55%	91.11%
CHEMBL2535	P11166	Glucose transporter	82.83%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.06%	95.50%
CHEMBL4208	P20618	Proteasome component C5	80.89%	90.00%

Plants that contains it

• Piper crassinervium
• Piper longum
• Piper retrofractum

Cross-Links

• PubChem: 64860
• LOTUS: LTS0219755
• wikiData: Q27225779