Piperonal

Details

• Internal ID: e862fd9b-af08-463c-b699-a9120fb1c3a0
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: 1,3-benzodioxole-5-carbaldehyde
• SMILES (Canonical): C1OC2=C(O1)C=C(C=C2)C=O
• SMILES (Isomeric): C1OC2=C(O1)C=C(C=C2)C=O
• InChI: InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
• InChI Key: SATCULPHIDQDRE-UHFFFAOYSA-N
• Popularity: 1,352 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₆O₃
• Molecular Weight: 150.13 g/mol
• Exact Mass: 150.031694049 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 120-57-0
• Piperonyl aldehyde
• Heliotropine
• Heliotropin
• 1,3-Benzodioxole-5-carbaldehyde
• Piperonaldehyde
• Piperonylaldehyde
• 3,4-Methylenedioxybenzaldehyde
• Geliotropin
• 1,3-Benzodioxole-5-carboxaldehyde
• 3,4-(Methylenedioxy)benzaldehyde
• 5-Formyl-1,3-benzodioxole
• Protocatechuic aldehyde methylene ether
• 3,4-Bis(methylenedioxy)benzaldehyde
• 3,4-Dihydroxybenzaldehyde methylene ketal
• Dioxymethylene-protocatechuic aldehyde
• 3,4-Dimethylenedioxybenzaldehyde
• Benzo[D][1,3]Dioxole-5-Carbaldehyde
• Heliotropin (natural)
• 3,4-Methylene-dihydroxybenzaldehyde
• FEMA No. 2911
• benzo[1,3]dioxole-5-carbaldehyde
• Dioxymethylene protocatechuic aldehyde
• NSC 26826
• Benzaldehyde, 3,4-(methylenedioxy)-
• CCRIS 5928
• HSDB 581
• EINECS 204-409-7
• UNII-KE109YAK00
• 5-Formylbenzodioxole
• CHEBI:8240
• KE109YAK00
• DTXSID7025924
• AI3-01198
• NSC-26826
• 2H-1,3-Benzodioxole-5-Carbaldehyde
• DTXCID505924
• 3,4-methylenedioxy-benzaldehyde
• EC 204-409-7
• 3,4-METHYLEN-DIOXY-BENZALDEHYDE
• 1,3-BENZODIOXOLE-6-CARBOXALDEHYDE
• DIOXYMETHYLENEPROTOCATECHUIC ALDEHYDE
• PIPERONAL (MART.)
• PIPERONAL [MART.]
• 2H-BENZO(3,4-D)-1,3-DIOXOLAN-5-YLFORMALDEHYDE
• heliotrin
• Piperonale
• Piperanal
• Pperonyl aldehyde
• Blue P
• Piperonal, 8CI
• Piperonal (8CI)
• 5-Formilbenzodioxole
• Piperonal, 99%
• PIPERONAL [FCC]
• Heliotropine (piperonal)
• PIPERONAL [MI]
• PIPERONAL [FHFI]
• PIPERONAL [HSDB]
• 4-methylenedioxybenzaldehyde
• 5-formil-1,3-benzodioxol
• HELIOTROPINE [INCI]
• PIPERONAL [WHO-DD]
• 5-Formyl-1 3-benzodioxole
• SCHEMBL29318
• 5-formil-1,3-benzodioxolane
• 5-Formyl-1 3-benzodioxolane
• HELIOTROPINE, PIPERONAL
• Piperonal, analytical standard
• 3,4-Methylendioxy-benzaldehyde
• 3,4-Dimetilenodioxibenzaldehido
• CHEMBL271663
• 3,4 -methylenedioxybenzaldehyde
• 3,4-methylene-dioxybenzaldehyde
• 3,4-methylenedioxy benzaldehyde
• 1,3-benzodioxol-5-carbaldehyde
• 3 4-Dimethylenedioxybenzaldehyde
• Piperonal, natural, 98%, FG
• 13-Benzodioxol-5-carboxaldehyde
• FEMA 2911
• 3 4-(Methylenedioxy)benzaldehyde
• 3,4-(Metilendioxi) benzaldehido
• Benzaldehyde,4-(methylenedioxy)-
• benzo[1,3]dioxol-5-carbaldehyde
• 3,4-methylenedihydroxybenzaldehyde
• 3,4-(methylenedioxy)-benzaldehyde
• BDBM153298
• benzo-1,3-dioxole-5-carbaldehyde
• Benzo[1 3]dioxole-5-carbaldehyde
• Piperonal, >=99%, FCC, FG
• WLN: T56 BO DO CHJ GVH
• 1,3-Benzodiolole-5-carboxaldehyde
• 3, 4-(Methylenedioxy)benzaldehyde
• NSC26826
• 1,3-Benzodioxole-5-carbaldehyde #
• benzo[1,3]dioxole-5-carboxaldehyde
• Tox21_200120
• 5-FORMYL-1,3-BENZODIOXOLANE
• BBL007668
• LS-631
• STK188426
• 3, 4-Bis(methylenedioxy)benzaldehyde
• AKOS002662846
• Benzo[d][1 3]dioxole-5-carboxaldehyde
• NCGC00091137-01
• NCGC00091137-02
• NCGC00257674-01
• 1,3-Benzodioxole-5-carboxaldehyde, 9CI
• 3 4-Dihydroxybenzaldehyde methylene ketal
• AC-11587
• benzo[d]-1,3-dioxolane-5-carboxaldehyde
• CAS-120-57-0
• 3,4-Methylenedioxybenzaldehyde (Piperonal)
• benzo [d] [1,3] dioxole-5-carboxaldehida
• P0456
• PIPERONAL (CONSTITUENT OF BLACK PEPPER)
• 2H-benzo [3,4-d]-1,3-dioxolan-5-ylformaldehido
• 2H-Benzo[3 4-d]-1 3-dioxolan-5-ylformaldehyde
• Q418985
• J-523977
• PIPERONAL (CONSTITUENT OF BLACK PEPPER) [DSC]
• InChI=1/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H
• 5XC

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8885	88.85%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7395	73.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9490	94.90%
OATP1B3 inhibitior	+	0.9566	95.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9266	92.66%
P-glycoprotein inhibitior	-	0.9833	98.33%
P-glycoprotein substrate	-	0.9920	99.20%
CYP3A4 substrate	-	0.7613	76.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7662	76.62%
CYP3A4 inhibition	-	0.6551	65.51%
CYP2C9 inhibition	-	0.7487	74.87%
CYP2C19 inhibition	-	0.6684	66.84%
CYP2D6 inhibition	-	0.5956	59.56%
CYP1A2 inhibition	+	0.8959	89.59%
CYP2C8 inhibition	-	0.9770	97.70%
CYP inhibitory promiscuity	+	0.5270	52.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4879	48.79%
Eye corrosion	-	0.7825	78.25%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.7966	79.66%
Skin corrosion	-	0.7319	73.19%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6683	66.83%
Micronuclear	+	0.5095	50.95%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	+	0.8137	81.37%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.6366	63.66%
Acute Oral Toxicity (c)	III	0.8039	80.39%
Estrogen receptor binding	-	0.7874	78.74%
Androgen receptor binding	+	0.5228	52.28%
Thyroid receptor binding	-	0.7546	75.46%
Glucocorticoid receptor binding	-	0.9251	92.51%
Aromatase binding	-	0.8231	82.31%
PPAR gamma	-	0.7281	72.81%
Honey bee toxicity	-	0.8931	89.31%
Biodegradation	+	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8060	80.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	2818.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.50%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.16%	95.56%
CHEMBL2039	P27338	Monoamine oxidase B	95.08%	92.51%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.79%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.57%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.37%	94.45%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	90.45%	85.30%
CHEMBL1951	P21397	Monoamine oxidase A	89.75%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.07%	86.33%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	85.80%	80.96%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.88%	96.00%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	84.27%	93.24%
CHEMBL3401	O75469	Pregnane X receptor	83.86%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.08%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.70%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.13%	100.00%

Plants that contains it

• Achillea grandifolia
• Asplenium adiantum-nigrum
• Brickellia longifolia
• Bupleurum rigidum
• Carpesium longifolium
• Cinnamomum parthenoxylon
• Cochlearia officinalis
• Coelogyne nitida
• Crocus corsicus
• Dichotomanthes tristaniicarpa
• Distemonanthus benthamianus
• Dracontium spruceanum
• Euphorbia micractina
• Frullania brasiliensis
• Galium verum
• Heliotropium lasiocarpum
• Heptapleurum venulosum
• Homalium laurifolium
• Lychnis coronata
• Matsumurella chinensis
• Palisota barteri
• Piper kwashoense
• Piper nigrum
• Piper retrofractum
• Retrophyllum minus
• Robinia pseudoacacia
• Rostrinucula dependens
• Verbesina virginica

Cross-Links

• PubChem: 8438
• NPASS: NPC120066
• ChEMBL: CHEMBL271663
• LOTUS: LTS0194867
• wikiData: Q418985