Isosafrole

Details

• Internal ID: 92ec4afe-3c27-45d1-804b-8117b644dcde
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: 5-[(E)-prop-1-enyl]-1,3-benzodioxole
• SMILES (Canonical): CC=CC1=CC2=C(C=C1)OCO2
• SMILES (Isomeric): C/C=C/C1=CC2=C(C=C1)OCO2
• InChI: InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+
• InChI Key: VHVOLFRBFDOUSH-NSCUHMNNSA-N
• Popularity: 486 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): 18.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.45
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• beta-Isosafrole
• 120-58-1
• Izosafrol
• (E)-Isosafrole
• Isosafrol
• trans-Isosafrole
• RCRA waste number U141
• Isosafrole (TGMX)
• 4043-71-4
• 5-(1-Propenyl)-1,3-benzodioxole
• 4-Propenyl-1,2-methylenedioxybenzene
• 1,3-Benzodioxole, 5-(1-propenyl)-
• 4-Propenylcatechol methylene ether
• 5-Prop-1-enyl-1,3-benzodioxole
• 5-[(E)-prop-1-enyl]-1,3-benzodioxole
• 5-[(E)-prop-1-enyl]benzo[1,3]dioxole
• NSC 4884
• 6-(1-Propenyl)-1,3-benzodioxole
• Benzene, 1,2-(methylenedioxy)-4-propenyl-
• .beta.-Isosafrole
• 1,2-Methylenedioxy-4-propenylbenzene
• 1,3-Benzodioxole, 5-(1-propenyl)-, (E)-
• CCRIS 353
• 3,4-(Methylenedioxy)-1-propenylbenzene
• Benzene, 1,2-(methylenedioxy)-4-propenyl-, (E)-
• HSDB 2862
• trans-1,2-(Methylenedioxy)-4-propenylbenzene
• EINECS 204-410-2
• RCRA waste no. U141
• 3,4-Methylenedioxy-1-propenyl benzene
• BRN 0082640
• UNII-94BY31ALL6
• AI3-02068
• MLS001055464
• 94BY31ALL6
• CHEBI:6054
• UNII-W6337429LF
• 5-[(1E)-prop-1-en-1-yl]-1,3-benzodioxole
• SMR001227197
• 1,3-Benzodioxole, 5-(1-propen-1-yl)-
• 5-19-01-00552 (Beilstein Handbook Reference)
• DTXCID00767
• Isosafrole (6CI)
• 1,2-(Methylenedioxy)-4-propenylbenzene
• CAS-120-58-1
• DTXSID2020767
• 6-(1-propenil)-1,3-benzodioxol
• 6-(1-Propenyl)-1 3-benzodioxole
• 1,3-benzodioxol,5-(1-propenil)-
• 5-(propen-1-il)-1,3-benzodioxol
• NSC 59192
• NSC 92436
• 1,3-benzodioxol, 5-(1-propenil)-
• 5-(Propen-1-yl)-1 3-benzodioxole
• 3,4-(Metilendioxi)-1-propenilbenceno
• 1 2-(Methylenedioxy)-4-propenylbenzene
• 3 4-(Methylenedioxy)-1-propenylbenzene
• 5-(1-Propen-1-yl)-1,3-benzodioxole
• Isosafrole Delisted December 8, 2006
• benceno,1,2-(Metilendioxi)-4-propenil-
• 1,3-benzodioxol, 5-(1-propen-1-il)-
• 13-Benzodioxole 5-(1-propenyl)-(9CI)
• benceno, 1,2-(Metilendioxi)-4-propenil-
• 1,2-METHYLENEDIOXY-4-PROPENYL-BENZENE
• Benzene12-(methylenedioxy)-4-propenyl-(8CI)
• Isosafrol, 1,2-(Metilendioxi)-4-propenilbenceno
• 5-((1E)-1-propenyl)-1,3-benzodioxole
• Spectrum5_000388
• ISOSAFROLE, TRANS-
• 1,3-Benzodioxole, 5-(1E)-1-propen-1-yl-
• BSPBio_002813
• SPECTRUM300533
• SCHEMBL266169
• CHEMBL487603
• cid_637796
• BDBM74206
• VHVOLFRBFDOUSH-NSCUHMNNSA-N
• DTXSID201316597
• HMS1373B16
• ISOSAFROLE TRANS-FORM [MI]
• Tox21_201783
• Tox21_302946
• 5-trans-propenyl-benzo-1,3-dioxole
• BBL027540
• CCG-38570
• STK801280
• AKOS001684145
• LS-7468
• SDCCGMLS-0066561.P001
• W6337429LF
• NCGC00090700-01
• NCGC00090700-02
• NCGC00090700-03
• NCGC00090700-04
• NCGC00090700-05
• NCGC00090700-06
• NCGC00256538-01
• NCGC00259332-01
• LS-30877
• BB 0261403
• (E)-5-(prop-1-enyl)benzo[d][1,3]dioxole
• 5-[(1E)-1-Propenyl]-1,3-benzodioxole #
• SR-05000002391
• 5-[(1E)-prop-1-en-1-yl]-2H-1,3-benzodioxole
• Q1088741
• SR-05000002391-1
• BRD-K44005821-001-07-4
• InChI=1/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9240	92.40%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5450	54.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9457	94.57%
OATP1B3 inhibitior	+	0.9640	96.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8080	80.80%
P-glycoprotein inhibitior	-	0.9914	99.14%
P-glycoprotein substrate	-	0.9465	94.65%
CYP3A4 substrate	-	0.7355	73.55%
CYP2C9 substrate	+	0.5556	55.56%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	-	0.7814	78.14%
CYP2C9 inhibition	-	0.5646	56.46%
CYP2C19 inhibition	+	0.6222	62.22%
CYP2D6 inhibition	-	0.5173	51.73%
CYP1A2 inhibition	+	0.9098	90.98%
CYP2C8 inhibition	-	0.9390	93.90%
CYP inhibitory promiscuity	+	0.7883	78.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Warning	0.5444	54.44%
Eye corrosion	-	0.8854	88.54%
Eye irritation	+	0.9897	98.97%
Skin irritation	+	0.8623	86.23%
Skin corrosion	-	0.6935	69.35%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5491	54.91%
Micronuclear	-	0.5379	53.79%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	+	0.8309	83.09%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.5706	57.06%
Acute Oral Toxicity (c)	III	0.8737	87.37%
Estrogen receptor binding	-	0.6975	69.75%
Androgen receptor binding	+	0.7743	77.43%
Thyroid receptor binding	-	0.7649	76.49%
Glucocorticoid receptor binding	-	0.9018	90.18%
Aromatase binding	-	0.8533	85.33%
PPAR gamma	-	0.7539	75.39%
Honey bee toxicity	-	0.9231	92.31%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.8333	83.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	10000 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2039	P27338	Monoamine oxidase B	99.08%	92.51%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.36%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.50%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.15%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.30%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.15%	86.33%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	90.49%	80.96%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	90.41%	85.30%
CHEMBL1951	P21397	Monoamine oxidase A	89.90%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.63%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.56%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.29%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.26%	89.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.05%	90.24%
CHEMBL2581	P07339	Cathepsin D	83.19%	98.95%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	82.21%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.94%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.00%	90.00%

Plants that contains it

• Angelica acutiloba
• Angelica sinensis
• Artemisia rupestris
• Asarum heterotropoides
• Asarum sieboldii
• Lantana camara
• Murraya koenigii
• Myristica fragrans
• Nectandra hihua
• Piper sanctum
• Sassafras albidum

Cross-Links

• PubChem: 637796
• NPASS: NPC127326
• ChEMBL: CHEMBL487603
• LOTUS: LTS0096972
• wikiData: Q1088741