Methyl 4-hydroxy-3-methoxy-cinnamate

Details

• Internal ID: 65a8e6e2-8054-495f-aa41-a4ffb74a5c23
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C=CC(=O)OC)O
• InChI: InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3
• InChI Key: AUJXJFHANFIVKH-UHFFFAOYSA-N
• Popularity: 37 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): 1.59
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• AUJXJFHANFIVKH-UHFFFAOYSA-N
• DTXSID801347441
• methyl 3-methoxy-4-hydroxycinnamate
• methyl 4-hydroxy-3-methoxy-cinnamate
• METHYL-4-HYDROXY-3-METHOXYCINNAMATE
• FT-0698057
• FT-0772817

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.8438	84.38%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8623	86.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9597	95.97%
OATP1B3 inhibitior	+	0.9798	97.98%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7154	71.54%
P-glycoprotein inhibitior	-	0.9786	97.86%
P-glycoprotein substrate	-	0.9604	96.04%
CYP3A4 substrate	-	0.6169	61.69%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.8380	83.80%
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	+	0.5404	54.04%
CYP inhibitory promiscuity	-	0.8081	80.81%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7197	71.97%
Carcinogenicity (trinary)	Non-required	0.6339	63.39%
Eye corrosion	+	0.4560	45.60%
Eye irritation	+	0.9866	98.66%
Skin irritation	+	0.7105	71.05%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6784	67.84%
Micronuclear	+	0.5507	55.07%
Hepatotoxicity	-	0.7876	78.76%
skin sensitisation	-	0.8309	83.09%
Respiratory toxicity	-	0.8111	81.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.7214	72.14%
Acute Oral Toxicity (c)	III	0.6244	62.44%
Estrogen receptor binding	+	0.8008	80.08%
Androgen receptor binding	+	0.6566	65.66%
Thyroid receptor binding	-	0.7265	72.65%
Glucocorticoid receptor binding	-	0.7404	74.04%
Aromatase binding	-	0.5159	51.59%
PPAR gamma	-	0.7754	77.54%
Honey bee toxicity	-	0.9508	95.08%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9647	96.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.54%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.80%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.33%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.86%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.34%	96.09%
CHEMBL3194	P02766	Transthyretin	90.21%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.17%	99.17%
CHEMBL4208	P20618	Proteasome component C5	87.01%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.80%	89.62%
CHEMBL2535	P11166	Glucose transporter	84.74%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.85%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	82.45%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.33%	94.45%

Plants that contains it

• Actaea racemosa
• Allium cepa
• Aristolochia kaempferi
• Artemisia capillaris
• Aster indicus
• Atalantia buxifolia
• Brickellia longifolia
• Brucea javanica
• Bupleurum rigidum
• Calamus draco
• Carpesium longifolium
• Cestrum parqui
• Citrus medica
• Cochlearia officinalis
• Coelogyne nitida
• Coreopsis grandiflora
• Crocus corsicus
• Dichotomanthes tristaniicarpa
• Dracontium spruceanum
• Euphorbia micractina
• Excoecaria acerifolia
• Frullania brasiliensis
• Garrya laurifolia
• Goupia glabra
• Heptapleurum venulosum
• Hibiscus taiwanensis
• Homalium laurifolium
• Houttuynia cordata
• Iris milesii
• Laggera alata
• Ligularia fischeri
• Lychnis coronata
• Matsumurella chinensis
• Medinilla magnifica
• Mesua ferrea
• Moringa oleifera
• Murraya paniculata
• Neomirandea parasitica
• Onobrychis bobrovii
• Palisota barteri
• Papaver persicum
• Petteria ramentacea
• Phellodendron chinense
• Phellodendron chinense var. glabriusculum
• Phyllanthus oligospermus
• Piper lhotzkyanum
• Piper retrofractum
• Pisonia umbellifera
• Retrophyllum minus
• Sabia japonica
• Senecio cathcartensis
• Sequoia sempervirens
• Spiraea formosana
• Stereospermum acuminatissimum
• Syncarpha gnaphaloides
• Taraxacum mongolicum
• Tetragonia tetragonoides
• Verbesina virginica

Cross-Links

• PubChem: 16830
• NPASS: NPC53773
• LOTUS: LTS0047572
• wikiData: Q104918972