3,4-Methylenedioxycinnamic acid

Details

• Internal ID: 8512a025-6f52-454b-b582-fc93ac531a41
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (E)-3-(1,3-benzodioxol-5-yl)prop-2-enoic acid
• SMILES (Canonical): C1OC2=C(O1)C=C(C=C2)C=CC(=O)O
• SMILES (Isomeric): C1OC2=C(O1)C=C(C=C2)/C=C/C(=O)O
• InChI: InChI=1S/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H,6H2,(H,11,12)/b4-2+
• InChI Key: QFQYZMGOKIROEC-DUXPYHPUSA-N
• Popularity: 43 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈O₄
• Molecular Weight: 192.17 g/mol
• Exact Mass: 192.04225873 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 3,4-(METHYLENEDIOXY)CINNAMIC ACID
• 38489-76-8
• X8H0WPJ08Y
• NSC-5953
• 2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-, (E)-
• 3,4-METHYLENEDIOXYCINNAMIC ACID, (E)-
• 3,4-METHYLENEDIOXYCINNAMIC ACID [WHO-DD]
• (2E)-3-(1,3-dioxaindan-5-yl)prop-2-enoic acid
• RefChem:486416
• 2Propenoic acid, 3(1,3benzodioxol5yl)
• 3,4(Methylenedioxy)cinnamic acid, predominantly trans
• 349541-65-7
• 887-122-5
• 2373-80-0
• 3-(Benzo[d][1,3]dioxol-5-yl)acrylic acid
• (2E)-3-(1,3-Benzodioxol-5-yl)-2-propenoic acid
• (E)-3-(1,3-benzodioxol-5-yl)prop-2-enoic acid
• (2e)-3-(1,3-benzodioxol-5-yl)acrylic acid
• MFCD00005837
• 3-(1,3-benzodioxol-5-yl)acrylic acid
• 2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-
• CHEBI:81482
• (2E)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid
• Methylenedioxycinnamic acid
• (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylic acid
• CHEMBL1173153
• 3,4-Methylenedioxy Cinnamic Acid
• 3,4-(Methylenedioxy)cinnamic acid, predominantly trans
• 2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-, (2E)-
• 3-(1,3-benzodioxol-5-yl)-2-propenoic acid
• Acetic acid, piperonylidene-
• (2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoic acid
• UNII-X8H0WPJ08Y
• 3-benzo[1,3]dioxol-5-yl-acrylic acid
• 3,4-Methylenedioxybenzene-3-acrylic acid
• 3-(3,4-Methylenedioxyphenyl)propenoic acid
• piperonyl acrylic acid
• Cinnamic acid, 3,4-(methylenedioxy)-
• 3-Piperonylacrylic Acid
• SCHEMBL79427
• 3,4-methylendioxycinnamic acid
• orb1296888
• SCHEMBL29690600
• (E)-Piperonylprop-2-enoic acid
• DTXSID80901400
• HMS1397A21
• ALBB-011737
• BBL012089
• BDBM50486070
• SBB042499
• STK020097
• AKOS000120493
• CS-W010709
• FM71196
• HY-W009993
• JS-3011
• (E)-3,4-(Methylenedioxy)cinnamic acid
• s11884
• NCGC00182231-01
• 3-(1,3-Benzodioxol-5-yl)propenoic acid
• TS-09982
• Cinnamic acid, 3,4-(methylenebis(oxy))-
• 3-(3,4-methylenedioxyphenyl) acrylic acid
• 3-(1,3-dioxaindan-5-yl)prop-2-enoic acid
• M0634
• NS00049336
• ST45026880
• EN300-16833
• 3,4-(Methylenedioxy)cinnamic acid, pred.trans
• C18077
• EN300-331721
• (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylicacid
• (e)-3-(1,3-benzodioxol-5-yl)-2-propenoic acid
• 373M800
• CS-002/03843060
• F019262
• F554574
• (2E)a3a(2Ha1,3aBenzodioxola5ayl)propa2aenoic acid
• Q27155410
• Z56789057
• F2191-0041
• 3,4-(METHYLENEDIOXY)CINNAMIC ACID predominantly trans
• (2E)-3-(2H-benzo[d]1,3-dioxolen-5-yl)prop-2-enoic acid
• 3,4-(Methylenedioxy)cinnamic acid, predominantly trans, 99%
• (2E)-3-(2H-benzo[3,4-d]1,3-dioxolen-5-yl)prop-2-enoic acid
• (E)-3-(1,3-Benzodioxol-5-yl)prop-2-enoic acid; Piperonyl acrylic acid
• InChI=1/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H,6H2,(H,11,12)/b4-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.7989	79.89%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7000	70.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9628	96.28%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7878	78.78%
P-glycoprotein inhibitior	-	0.9898	98.98%
P-glycoprotein substrate	-	0.9867	98.67%
CYP3A4 substrate	-	0.7421	74.21%
CYP2C9 substrate	-	0.5947	59.47%
CYP2D6 substrate	-	0.8760	87.60%
CYP3A4 inhibition	-	0.5678	56.78%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8893	88.93%
CYP inhibitory promiscuity	-	0.6379	63.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4513	45.13%
Eye corrosion	-	0.9328	93.28%
Eye irritation	+	0.9819	98.19%
Skin irritation	+	0.7303	73.03%
Skin corrosion	-	0.8192	81.92%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7919	79.19%
Micronuclear	+	0.5495	54.95%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	+	0.7089	70.89%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6881	68.81%
Acute Oral Toxicity (c)	III	0.7117	71.17%
Estrogen receptor binding	-	0.5925	59.25%
Androgen receptor binding	+	0.9141	91.41%
Thyroid receptor binding	-	0.6278	62.78%
Glucocorticoid receptor binding	-	0.8758	87.58%
Aromatase binding	-	0.6911	69.11%
PPAR gamma	+	0.6893	68.93%
Honey bee toxicity	-	0.9462	94.62%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7652	76.52%
Fish aquatic toxicity	+	0.9099	90.99%

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	96.97%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.85%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	92.21%	94.80%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.99%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.37%	96.00%
CHEMBL2039	P27338	Monoamine oxidase B	90.84%	92.51%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.69%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.61%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.52%	94.45%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.18%	85.30%
CHEMBL4208	P20618	Proteasome component C5	80.79%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.26%	99.17%

Plants that contains it

• Asplenium adiantum-nigrum
• Brombya platynema
• Distemonanthus benthamianus
• Helichrysum arenarium
• Piper kwashoense

Cross-Links

• PubChem: 643181
• NPASS: NPC57501
• ChEMBL: CHEMBL1173153
• LOTUS: LTS0236790
• wikiData: Q27155410