Piperic acid

Details

• Internal ID: a08af686-d584-4179-8e85-e891f740ef2c
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
• SMILES (Canonical): C1OC2=C(O1)C=C(C=C2)C=CC=CC(=O)O
• SMILES (Isomeric): C1OC2=C(O1)C=C(C=C2)/C=C/C=C/C(=O)O
• InChI: InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1+,4-2+
• InChI Key: RHBGITBPARBDPH-ZPUQHVIOSA-N
• Popularity: 50 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.20 g/mol
• Exact Mass: 218.05790880 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• (E,E)-piperic acid
• 136-72-1
• Piperonic acid
• 5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoic acid
• Piperic acid (E,E)-form
• Piperinic Acid
• (2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
• GFG3FLA9UR
• NSC129538
• trans,trans-piperinic acid
• NSC-129538
• 5285-18-7
• CHEBI:37316
• (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
• (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoic acid
• 5-(1,3-benzodioxol-5-yl)-2,4-pentadienoic acid
• NSC 129538
• 2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)-, (E,E)-
• (E,E)-Piperonic Acid
• SR-01000309042
• UNII-GFG3FLA9UR
• Piperinsaure
• PIPERIC ACID [MI]
• SCHEMBL447578
• CHEMBL332122
• PIPERIC ACID, (E,E)-
• DTXSID801016979
• BDBM50381226
• CCG-37574
• NCI129538
• 2, 5-(1,3-benzodioxol-5-yl)-
• AKOS005084354
• EN300-7461567
• 1X-0937
• J-006896
• Q1111585
• SR-01000309042-1
• SR-01000309042-2
• 5-(Benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoicacid
• (2E,4E)-5-(1,3-dioxaindan-5-yl)penta-2,4-dienoic acid
• 5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoic acid, 97%
• 5-(3,4-METHYLENEDIOXYPHENYL)-2,4-PENTADIENOICACID
• (E,E)-5-(3,4-METHYLENEDIOXYPHENYL)-2,4-PENTADIENOIC ACID

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.7624	76.24%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7000	70.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9583	95.83%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5873	58.73%
P-glycoprotein inhibitior	-	0.9732	97.32%
P-glycoprotein substrate	-	0.9799	97.99%
CYP3A4 substrate	-	0.6703	67.03%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.8907	89.07%
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	-	0.8837	88.37%
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	+	0.9217	92.17%
Skin irritation	+	0.7303	73.03%
Skin corrosion	-	0.8192	81.92%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7403	74.03%
Micronuclear	+	0.5495	54.95%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	+	0.7089	70.89%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6458	64.58%
Acute Oral Toxicity (c)	III	0.7117	71.17%
Estrogen receptor binding	+	0.6548	65.48%
Androgen receptor binding	+	0.9021	90.21%
Thyroid receptor binding	-	0.4949	49.49%
Glucocorticoid receptor binding	-	0.6852	68.52%
Aromatase binding	+	0.8662	86.62%
PPAR gamma	+	0.6454	64.54%
Honey bee toxicity	-	0.9402	94.02%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6752	67.52%
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
CHEMBL2039	P27338	Monoamine oxidase B	98.12%	92.51%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.86%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.88%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.08%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.75%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.40%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.98%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.40%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.99%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.53%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	80.51%	94.73%

Plants that contains it

• Piper tuberculatum

Cross-Links

• PubChem: 5370536
• LOTUS: LTS0215880
• wikiData: Q1111585