gamma-Asarone

Details

• Internal ID: 2e68c6ae-2176-4b9a-9a90-bb14f2c67be9
• Taxonomy: Benzenoids > Phenol ethers > Anisoles
• IUPAC Name: 1,2,4-trimethoxy-5-prop-2-enylbenzene
• SMILES (Canonical): COC1=CC(=C(C=C1CC=C)OC)OC
• SMILES (Isomeric): COC1=CC(=C(C=C1CC=C)OC)OC
• InChI: InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5,7-8H,1,6H2,2-4H3
• InChI Key: AUNAUZZQBAIQFJ-UHFFFAOYSA-N
• Popularity: 287 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25 g/mol
• Exact Mass: 208.109944368 g/mol
• Topological Polar Surface Area (TPSA): 27.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 5353-15-1
• 1,2,4-trimethoxy-5-prop-2-enylbenzene
• 1-allyl-2,4,5-trimethoxybenzene
• 2,4,5-Trimethoxy-1-allylbenzene
• 2,4,5-Trimethoxyallylbenzene
• isoasarone
• Euasarone
• Sekishon
• Benzene, 1,2,4-trimethoxy-5-(2-propenyl)-
• 1,2,4-trimethoxy-5-(prop-2-en-1-yl)benzene
• BENZENE,1,2,4-TRIMETHOXY-5-(2-PROPENYL)-
• D4G4B8R48N
• 1-allyl-2,4,5-trimethoxy-benzene
• 1,2,4-Trimethoxy-5-(2-propenyl)benzene
• Benzene, 1,2,4-trimethoxy-5-(2-propen-1-yl)-
• Sekishone
• g-Asarone
• .gamma.-Asarone
• starbld0004187
• UNII-D4G4B8R48N
• SCHEMBL942820
• CHEBI:81353
• DTXSID10201743
• 2-Allyl-1,4,5-trimethoxybenzene
• HY-N7937
• AKOS034170705
• Benzene, 1-allyl-2,4,5-trimethoxy-
• AS-79279
• 1,2,4-Trimethoxy-5-(2-propenyl)-Benzene
• CS-0138838
• C17821
• E88991
• EN300-1721796
• 1,2,4-TRIMETHOXY-5-(2-PROPEN-1-YL)BENZENE
• Q27155291
• Z3178023286
• InChI=1/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5,7-8H,1,6H2,2-4H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.8039	80.39%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7279	72.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7577	75.77%
OATP1B3 inhibitior	+	0.9700	97.00%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7637	76.37%
P-glycoprotein inhibitior	-	0.9555	95.55%
P-glycoprotein substrate	-	0.9216	92.16%
CYP3A4 substrate	-	0.6903	69.03%
CYP2C9 substrate	+	0.6000	60.00%
CYP2D6 substrate	+	0.4914	49.14%
CYP3A4 inhibition	-	0.6828	68.28%
CYP2C9 inhibition	-	0.9587	95.87%
CYP2C19 inhibition	-	0.6414	64.14%
CYP2D6 inhibition	-	0.9204	92.04%
CYP1A2 inhibition	+	0.5354	53.54%
CYP2C8 inhibition	-	0.7046	70.46%
CYP inhibitory promiscuity	+	0.7026	70.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7421	74.21%
Carcinogenicity (trinary)	Non-required	0.5471	54.71%
Eye corrosion	-	0.6042	60.42%
Eye irritation	+	0.8836	88.36%
Skin irritation	-	0.6498	64.98%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4108	41.08%
Micronuclear	-	0.7108	71.08%
Hepatotoxicity	+	0.7659	76.59%
skin sensitisation	-	0.5419	54.19%
Respiratory toxicity	-	0.9556	95.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.5255	52.55%
Acute Oral Toxicity (c)	III	0.8438	84.38%
Estrogen receptor binding	-	0.8497	84.97%
Androgen receptor binding	-	0.8967	89.67%
Thyroid receptor binding	-	0.7469	74.69%
Glucocorticoid receptor binding	-	0.8983	89.83%
Aromatase binding	-	0.7286	72.86%
PPAR gamma	-	0.8831	88.31%
Honey bee toxicity	-	0.7605	76.05%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9609	96.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.72%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.57%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.40%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.91%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.14%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.59%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.85%	95.56%
CHEMBL4208	P20618	Proteasome component C5	80.80%	90.00%

Plants that contains it

• Acanthosyris paulo-alvinii
• Aconitum episcopale
• Acorus calamus
• Acorus calamus var. angustatus
• Acorus gramineus
• Aglaia perviridis
• Aniba hostmanniana
• Aniba puchury-minor
• Ardisia humilis
• Ardisia japonica
• Asarum asperum var. geaster
• Asarum heterotropoides
• Asarum sieboldii
• Asarum trigynum
• Betula alnoides
• Caesulia axillaris
• Cornus officinalis
• Garcinia oligantha
• Iris spuria
• Phoebe grandis
• Piper divaricatum
• Piper kadsura
• Piper marginatum
• Piper sarmentosum
• Rubus pileatus
• Rubus trifidus

Cross-Links

• PubChem: 636750
• NPASS: NPC7343
• LOTUS: LTS0252786
• wikiData: Q27155291