Acetosyringone

Details

• Internal ID: 2e67dd7b-bc7b-4337-8e93-3272af49bf5f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
• SMILES (Canonical): CC(=O)C1=CC(=C(C(=C1)OC)O)OC
• SMILES (Isomeric): CC(=O)C1=CC(=C(C(=C1)OC)O)OC
• InChI: InChI=1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3
• InChI Key: OJOBTAOGJIWAGB-UHFFFAOYSA-N
• Popularity: 5,131 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: 0.20
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 2478-38-8
• 1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone
• 4'-HYDROXY-3',5'-DIMETHOXYACETOPHENONE
• Acetosyringenin
• 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one
• CHEBI:2404
• 866P45Y84S
• DTXSID2062454
• RefChem:552431
• DTXCID1037147
• 219-610-5
• 3',5'-Dimethoxy-4'-hydroxyacetophenone
• Ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-
• Acetosyringon
• 3,5-Dimethoxy-4-hydroxyacetophenone
• MFCD00008748
• Acetophenone, 4'-hydroxy-3',5'-dimethoxy-
• 4-hydroxy-3,5-dimethoxyacetophenone
• 4-Hydroksy-3',5'-dwumetoksyacetofenon
• Acetophenone, 3,5-dimethoxy-4-hydroxy-
• 4-Hydroxy-3,5-dimethoxyacetophennone
• 1-acetyl-4-hydroxy-3,5-dimethoxybenzene
• CCRIS 7286
• EINECS 219-610-5
• BRN 1966119
• 4-acetylsyringol
• UNII-866P45Y84S
• 4-Hydroksy-3',5'-dwumetoksyacetofenon [Polish]
• Spectrum_001915
• SpecPlus_000955
• Spectrum2_000429
• Spectrum3_001115
• Spectrum4_001953
• Spectrum5_000695
• 1-(4-hydroxy-3,5-dimethoxy-phenyl)ethanone
• bmse000576
• bmse010032
• 1-(4-Hydroxy-3,5-dimethoxy-phenyl)-ethanone
• SCHEMBL15511
• BSPBio_002850
• KBioGR_002389
• KBioSS_002457
• SPECTRUM300610
• MLS002207209
• DivK1c_007051
• 4-acetyl-2,6-dimethoxyphenol
• SPBio_000418
• CHEMBL224146
• orb1301663
• KBio1_001995
• KBio2_002450
• KBio2_005018
• KBio2_007586
• KBio3_002070
• Phenol, 4-acetyl-2,6-dimethoxy
• BBL101364
• CCG-39967
• MSK159295
• s4955
• SBB071453
• STL555160
• AKOS005258861
• 3',5-Dimethoxy-4'-hydroxyacetophenone
• CS-W010600
• FD16078
• HY-W009884
• SDCCGMLS-0066948.P001
• NCGC00095819-01
• NCGC00095819-02
• 3', 5'-dimethoxy-4'-hydroxyacetophenone
• MS-20205
• SMR000112388
• ST093688
• SY049152
• DB-022069
• TR-011399
• D2666
• NS00010763
• 1-(3,5-dimethoxy-4-oxidanyl-phenyl)ethanone
• 3',5'-Dimethoxy-4'-hydroxyacetophenone, 97%
• 4'-Hydroxy-3',5'-dimethoxyacetophenone, 97%
• EN300-112111
• F20446
• 3',5'-DIMETHOXY-4'-HYDROXY-ACETOPHENONE
• 478D388
• A817490
• F218999
• Q906309
• SR-05000002436
• A1-00327
• SR-05000002436-1
• Acetosyringone;4'-Hydroxy-3',5'-dimethoxyacetophenone
• BRD-K66643401-001-02-4
• BRD-K66643401-001-04-0
• Z1255450019
• 3 inverted exclamation marka,5 inverted exclamation marka-Dimethoxy-4 inverted exclamation marka-hydroxyacetophenone
• 4 inverted exclamation mark -Hydroxy-3 inverted exclamation mark ,5 inverted exclamation mark -dimethoxyacetophenone
• InChI=1/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.5300	53.00%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8813	88.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9387	93.87%
OATP1B3 inhibitior	+	0.9718	97.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9411	94.11%
P-glycoprotein inhibitior	-	0.9371	93.71%
P-glycoprotein substrate	-	0.9326	93.26%
CYP3A4 substrate	-	0.6577	65.77%
CYP2C9 substrate	-	0.8120	81.20%
CYP2D6 substrate	-	0.7369	73.69%
CYP3A4 inhibition	-	0.8467	84.67%
CYP2C9 inhibition	-	0.9944	99.44%
CYP2C19 inhibition	-	0.7886	78.86%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	-	0.7261	72.61%
CYP2C8 inhibition	-	0.7820	78.20%
CYP inhibitory promiscuity	-	0.8362	83.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7554	75.54%
Carcinogenicity (trinary)	Non-required	0.6658	66.58%
Eye corrosion	+	0.6642	66.42%
Eye irritation	+	0.9927	99.27%
Skin irritation	+	0.5756	57.56%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7754	77.54%
Micronuclear	-	0.5067	50.67%
Hepatotoxicity	+	0.5659	56.59%
skin sensitisation	-	0.8203	82.03%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.6515	65.15%
Acute Oral Toxicity (c)	III	0.6252	62.52%
Estrogen receptor binding	-	0.5527	55.27%
Androgen receptor binding	-	0.7980	79.80%
Thyroid receptor binding	-	0.7078	70.78%
Glucocorticoid receptor binding	-	0.8104	81.04%
Aromatase binding	-	0.8070	80.70%
PPAR gamma	-	0.9113	91.13%
Honey bee toxicity	-	0.9390	93.90%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7336	73.36%
Fish aquatic toxicity	+	0.8371	83.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	7.1 nM; 7.1 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.32%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.12%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.77%	99.17%
CHEMBL2535	P11166	Glucose transporter	85.53%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	83.61%	90.20%
CHEMBL4208	P20618	Proteasome component C5	83.35%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.66%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.21%	85.14%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.14%	97.21%

Plants that contains it

• Atropa belladonna
• Bulbine narcissifolia
• Hyoscyamus albus
• Imperata cylindrica
• Isatis tinctoria
• Justicia adhatoda
• Nicotiana tabacum
• Posidonia oceanica
• Saussurea costus
• Zanthoxylum bungeanum
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 17198
• NPASS: NPC208760
• ChEMBL: CHEMBL224146
• LOTUS: LTS0017449
• wikiData: Q906309