O-Methoxycinnamaldehyde, (E)-

Details

• Internal ID: 850c1b44-e7c2-401f-92d7-38343c7088ca
• Taxonomy: Phenylpropanoids and polyketides > Cinnamaldehydes
• IUPAC Name: (E)-3-(2-methoxyphenyl)prop-2-enal
• SMILES (Canonical): COC1=CC=CC=C1C=CC=O
• SMILES (Isomeric): COC1=CC=CC=C1/C=C/C=O
• InChI: InChI=1S/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+
• InChI Key: KKVZAVRSVHUSPL-GQCTYLIASA-N
• Popularity: 169 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.18 g/mol
• Exact Mass: 162.068079557 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.91
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• O-Methoxycinnamaldehyde, (E)-
• UNII-3GG2B2MUHB
• 3GG2B2MUHB
• 2-propenal, 3-(2-methoxyphenyl)-, (2E)-
• (2E)-3-(2-Methoxyphenyl)-2-propenal
• TRANS-O-METHOXYCINNAMALDEHYDE
• O-METHOXYCINNAMALDEHYDE, (2E)-
• 2-PROPENAL, 3-(2-METHOXYPHENYL)-, (E)-
• RefChem:43988
• 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM CASSIA BARK)
• 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM VERUM BARK)
• 2-Methoxycinnamaldehyde
• 1504-74-1
• 60125-24-8
• O-METHOXYCINNAMALDEHYDE
• (E)-3-(2-Methoxyphenyl)acrylaldehyde
• o-Methoxycinnamic aldehyde
• FEMA 3181
• Cinnamaldehyde, o-methoxy-
• (E)-3-(2-methoxyphenyl)prop-2-enal
• Cassiastearoptene
• 3-(2-Methoxyphenyl)acrylaldehyde
• (2E)-3-(2-Methoxyphenyl)Prop-2-Enal
• 2'-Methoxycinnamaldehyde
• trans-2-Methoxycinnamaldehyde
• 3-O-Methoxyphenyl-2-propenal
• beta-(o-Methoxyphenyl)acrolein
• o-Methoxycinnamicaldehyde crystals
• 3-(2-Methoxyphenyl)-2-propenal
• Ortho-Methoxycinnamaldehyde
• MFCD00007001
• o-Methoxy cinnamaldehyde
• 2-Methoxy Cinnamaldehyde
• 2-Methoxycinnamic aldehyde
• (2E)-3-(2-methoxyphenyl)acrylaldehyde
• CHEMBL83159
• Ortho methoxy cinnamic aldehyde
• DTXSID4047206
• 3-(2-methoxyphenyl)prop-2-enal
• A1D6H
• FEMA No. 3181
• CCRIS 3196
• O-Methoxyphenyl acrolein, beta-
• o-Methoxycinnamaldehyde (natural)
• (E)-O-methoxycinnamaldehyde
• Methoxycinnamaldehyde, o-
• EINECS 216-131-3
• DTXSID2025551
• NSC 114599
• .beta.-(o-Methoxyphenyl)acrolein
• BRN 2436856
• UNII-4940G3R6HE
• 2-Methoxycinnamaldehyde, predominantly trans
• 2-Methoxycimnamaldehyde
• O-Methoxy-Cinnamaldehyde
• beta-O-Methoxyphenyl acrolein
• 2-08-00-00149 (Beilstein Handbook Reference)
• SCHEMBL228813
• DTXCID405551
• orb2893305
• SCHEMBL2118830
• beta -(O-methoxyphenyl)acrolein
• SCHEMBL31004887
• DTXCID90809802
• 2-Propenyl-3-(2-methoxyphenol)
• CHEBI:180713
• 4940G3R6HE
• 2-Methoxycinnamaldehyde (Standard)
• HY-W046353R
• Tox21_202885
• Tox21_303635
• 3-(2-Methoxyphenyl)-2-propenal #
• BDBM50240642
• MSK157143
• s9482
• SBB040240
• (E)-3-(2-Methoxy-phenyl)-propenal
• AKOS000120956
• o-Methoxycinnamaldehyde, >=96%, FG
• FM71230
• HY-W046353
• 3-(2-Methoxyphenyl)-(2E)-2-propenal
• NCGC00256699-01
• NCGC00260431-01
• AS-15726
• DA-76420
• SY410145
• CAS-1504-74-1
• CAS-60125-24-8
• 2-Methoxycinnamaldehyde, natural, 98%, FG
• CS-0065992
• CS-0201507
• NS00012820
• ST50213399
• EN300-19948
• PK04_181244
• O10862
• EN300-6729490
• 2-Methoxycinnamaldehyde, predominantly trans, 96%
• F552129
• F610010
• BRD-K20078988-001-01-1
• Q27257183
• Z2573655488
• 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
• 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
• InChI=1/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8681	86.81%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8858	88.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9322	93.22%
OATP1B3 inhibitior	+	0.9904	99.04%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8940	89.40%
P-glycoprotein inhibitior	-	0.9858	98.58%
P-glycoprotein substrate	-	0.9612	96.12%
CYP3A4 substrate	-	0.6194	61.94%
CYP2C9 substrate	+	0.5954	59.54%
CYP2D6 substrate	-	0.7817	78.17%
CYP3A4 inhibition	-	0.9092	90.92%
CYP2C9 inhibition	-	0.8403	84.03%
CYP2C19 inhibition	+	0.6641	66.41%
CYP2D6 inhibition	-	0.9569	95.69%
CYP1A2 inhibition	+	0.8572	85.72%
CYP2C8 inhibition	-	0.8088	80.88%
CYP inhibitory promiscuity	+	0.5693	56.93%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6676	66.76%
Carcinogenicity (trinary)	Non-required	0.5004	50.04%
Eye corrosion	+	0.9497	94.97%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.7735	77.35%
Skin corrosion	-	0.9003	90.03%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5928	59.28%
Micronuclear	-	0.6437	64.37%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	+	0.7929	79.29%
Respiratory toxicity	-	0.8556	85.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	+	0.6967	69.67%
Acute Oral Toxicity (c)	III	0.8804	88.04%
Estrogen receptor binding	-	0.8466	84.66%
Androgen receptor binding	-	0.7752	77.52%
Thyroid receptor binding	-	0.8915	89.15%
Glucocorticoid receptor binding	-	0.8221	82.21%
Aromatase binding	-	0.7515	75.15%
PPAR gamma	-	0.8363	83.63%
Honey bee toxicity	-	0.8901	89.01%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9186	91.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.72%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.19%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.93%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.48%	91.11%
CHEMBL1255126	O15151	Protein Mdm4	81.57%	90.20%
CHEMBL2581	P07339	Cathepsin D	81.50%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.17%	95.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.08%	89.62%

Plants that contains it

• Cinnamomum aromaticum
• Cinnamomum verum
• Elettaria cardamomum
• Illicium verum
• Neolitsea cassia

Cross-Links

• PubChem: 641298
• NPASS: NPC84325
• ChEMBL: CHEMBL83159
• LOTUS: LTS0195380
• wikiData: Q27257183