Xanthoxylin

Details

• Internal ID: 6a06a128-d402-408e-becc-dfd59c1ae770
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone
• SMILES (Canonical): CC(=O)C1=C(C=C(C=C1OC)OC)O
• SMILES (Isomeric): CC(=O)C1=C(C=C(C=C1OC)OC)O
• InChI: InChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3
• InChI Key: FBUBVLUPUDBFME-UHFFFAOYSA-N
• Popularity: 185 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.20 g/mol
• Exact Mass: 196.07355886 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 90-24-4
• 2'-Hydroxy-4',6'-dimethoxyacetophenone
• Xanthoxyline
• Brevifolin
• 1-(2-Hydroxy-4,6-dimethoxyphenyl)ethanone
• 2-Hydroxy-4,6-dimethoxyacetophenone
• Brevifolin (Zanthoxylum)
• 1-(2-Hydroxy-4,6-dimethoxyphenyl)ethan-1-one
• 2,4-Di-O-methylphloroacetophenone
• Phloracetophenone dimethyl ether
• Phloroacetophenone 2,4-dimethyl ether
• Brevifolin (VAN)
• 4',6'-dimethoxy-2'-hydroxyacetophenone
• 4,6-Dimethoxy-2-hydroxyacetophenone
• Ethanone, 1-(2-hydroxy-4,6-dimethoxyphenyl)-
• 1-Acetyl-2-hydroxy-4,6-dimethoxybenzene
• Acetophenone der.
• UNII-Z8RSY5TZPA
• Z8RSY5TZPA
• MFCD00017243
• NSC 17392
• 2-Acetyl-3,5-dimethoxyphenol
• 1-(2-hydroxy-4,6-dimethoxy-phenyl)ethanone
• Acetophenone, 2'-hydroxy-4',6'-dimethoxy-
• CHEBI:10070
• EINECS 201-978-3
• NSC-17392
• 2-Hydroxyl-4,6-dimethoxy-acetophenone
• AI3-26010
• Ethanone,1-(2-hydroxy-4,6-dimethoxyphenyl)-
• 6-Methoxypaeonol
• Spectrum_000577
• SpecPlus_000713
• XANTHOXYLIN [MI]
• Spectrum2_000463
• Spectrum3_000181
• Spectrum4_001499
• Spectrum5_000237
• Acetophenone,6'-dimethoxy-
• SCHEMBL44708
• BSPBio_001701
• KBioGR_002137
• KBioSS_001057
• SPECTRUM200441
• MLS002207182
• DivK1c_006809
• XANTHOXYLINE [WHO-DD]
• SPBio_000566
• CHEMBL450288
• KBio1_001753
• KBio2_001057
• KBio2_003625
• KBio2_006193
• KBio3_001201
• DTXSID10237981
• HY-N1063
• NSC17392
• CCG-38702
• s4781
• 2-Hydroxy-4, 6-dimethoxyacetophenone
• 4, 6-Dimethoxy-2-hydroxyacetophenone
• AKOS015856339
• SDCCGMLS-0066937.P001
• 2'-hyroxy-4',6'-dimethoxyacetophenone
• PHLOROACETOPHENONE DIMETHYL ETHER
• NCGC00095824-01
• NCGC00095824-02
• AC-35124
• AS-40799
• SMR001306755
• SY048579
• 2'-Hydroxy-4',6'-dimethoxy-Acetophenone
• (2-hydroxy-4,6-dimethoxy-phenyl)-ethanone
• 1-(2-hydroxy-4,6-dimethoxyphenyl)-ethanone
• 1-(2-Hydroxy-4,6-dimethylphenyl)-ethanone
• CS-0016347
• D2683
• FT-0612544
• 1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-on
• 1-(2-Hydroxy-4,6-dimethoxyphenyl)ethanone #
• 2'-Hydroxy-4',6'-dimethoxyacetophenone, 97%
• 2',4'-DIMETHOXY-6'-HYDROXYACETOPHENONE
• EN300-6477862
• A843476
• AQ-358/42007313
• SR-05000002434
• 2''-HYDROXY-4'',6''-DIMETHOXYACETOPHENONE
• Acetophenone, 2'-hydroxy-4',6'-dimethoxy- (8CI)
• SR-05000002434-1
• BRD-K12260308-001-02-6
• BRD-K12260308-001-04-2
• Q18210424
• Z1255434817
• 2 inverted exclamation mark -Hydroxy-4 inverted exclamation mark ,6 inverted exclamation mark -dimethoxyacetophenone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	+	0.7296	72.96%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.9133	91.33%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.9526	95.26%
OATP1B3 inhibitior	+	0.9790	97.90%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9237	92.37%
P-glycoprotein inhibitior	-	0.9406	94.06%
P-glycoprotein substrate	-	0.9589	95.89%
CYP3A4 substrate	-	0.6326	63.26%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.8116	81.16%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9930	99.30%
CYP2C19 inhibition	-	0.7638	76.38%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.6098	60.98%
CYP2C8 inhibition	-	0.7378	73.78%
CYP inhibitory promiscuity	-	0.7918	79.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6688	66.88%
Carcinogenicity (trinary)	Non-required	0.7056	70.56%
Eye corrosion	+	0.6450	64.50%
Eye irritation	+	0.9615	96.15%
Skin irritation	+	0.5503	55.03%
Skin corrosion	-	0.9757	97.57%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6057	60.57%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8896	88.96%
Respiratory toxicity	-	0.8556	85.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.8875	88.75%
Nephrotoxicity	+	0.6306	63.06%
Acute Oral Toxicity (c)	III	0.5584	55.84%
Estrogen receptor binding	-	0.6951	69.51%
Androgen receptor binding	-	0.7378	73.78%
Thyroid receptor binding	-	0.6785	67.85%
Glucocorticoid receptor binding	-	0.8799	87.99%
Aromatase binding	-	0.5993	59.93%
PPAR gamma	-	0.6844	68.44%
Honey bee toxicity	-	0.9291	92.91%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6504	65.04%
Fish aquatic toxicity	+	0.8811	88.11%

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
CHEMBL4040	P28482	MAP kinase ERK2	28183.8 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	891.3 nM; 891.3 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.97%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.90%	85.14%
CHEMBL4208	P20618	Proteasome component C5	88.91%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.67%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.83%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.55%	95.56%
CHEMBL2535	P11166	Glucose transporter	85.24%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.29%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	82.98%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.84%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.89%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.83%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.20%	91.07%

Plants that contains it

• Acradenia frankliniae
• Artemisia annua
• Artemisia santolina
• Artemisia sericea
• Beaucarnea recurvata
• Canarium album
• Centaurea arenaria
• Centipeda minima
• Clausena excavata
• Cotylelobium scabriusculum
• Cratystylis conocephala
• Croton hieronymi
• Croton nepetifolius
• Diospyros abyssinica
• Diospyros elliptifolia
• Diospyros malabarica
• Euphorbia humifusa
• Euphorbia maculata
• Euphorbia plumerioides
• Euphorbia portulacoides
• Euphorbia quinquecostata
• Gutenbergia cordifolia
• Habranthus brachyandrus
• Hippomane mancinella
• Melicope borbonica
• Mikania scandens
• Phebalium filifolium
• Phyllanthus sellowianus
• Phyllanthus urinaria
• Phyllanthus virgatus
• Phyllodium pulchellum
• Pseudomarsupidium decipiens
• Pulicaria incisa
• Punica granatum
• Scorzonera hispanica
• Sebastiania schottiana
• Seriphidium gypsaceum
• Seriphidium herba-alba
• Seriphidium ifranensis
• Seriphidium maritimum subsp. maritimum
• Seriphidium spicigerum
• Trapa natans var. japonica
• Triadica sebifera
• Zanthoxylum bungeanum
• Zanthoxylum gilletii
• Zanthoxylum piasezkii

Cross-Links

• PubChem: 66654
• NPASS: NPC305518
• ChEMBL: CHEMBL450288
• LOTUS: LTS0150432
• wikiData: Q18210424