1-Propanone, 1-[2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-2-methyl-

Details

• Internal ID: 5d07fdab-639a-492c-be1e-897fb83002fc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2-methylpropan-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)O)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C=C(C=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O
• InChI: InChI=1S/C16H22O9/c1-6(2)12(20)11-8(19)3-7(18)4-9(11)24-16-15(23)14(22)13(21)10(5-17)25-16/h3-4,6,10,13-19,21-23H,5H2,1-2H3/t10-,13-,14+,15-,16-/m1/s1
• InChI Key: PSBKCHXAPMSDFN-LMXXTMHSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₉
• Molecular Weight: 358.34 g/mol
• Exact Mass: 358.12638228 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.88
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 17004-75-0
• 1-Propanone, 1-[2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-2-methyl-
• Compound NP-023002
• DTXSID501225064
• BDBM50269661
• AKOS040735588
• 1-(2-Methylpropanoyl)-phloroglucinol-glucopyranoside
• 1-(2-Methylpropanoyl)phloroglucinol glucopyranoside
• 1-[(2-Methylpropanoyl)phloroglucinyl]-beta-D-glucopyranoside
• 1-[2-(beta-d-glucopyranosyloxy)-4,6-dihydroxyphenyl]-2-methyl-1-propanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5983	59.83%
Caco-2	-	0.8817	88.17%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8064	80.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9104	91.04%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9711	97.11%
P-glycoprotein inhibitior	-	0.8982	89.82%
P-glycoprotein substrate	-	0.9138	91.38%
CYP3A4 substrate	-	0.5135	51.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.8282	82.82%
CYP2C9 inhibition	-	0.7776	77.76%
CYP2C19 inhibition	-	0.8871	88.71%
CYP2D6 inhibition	-	0.9102	91.02%
CYP1A2 inhibition	-	0.7765	77.65%
CYP2C8 inhibition	-	0.7972	79.72%
CYP inhibitory promiscuity	-	0.6975	69.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7596	75.96%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9127	91.27%
Skin irritation	-	0.8422	84.22%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4075	40.75%
Micronuclear	-	0.5908	59.08%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8464	84.64%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.5902	59.02%
Acute Oral Toxicity (c)	III	0.7771	77.71%
Estrogen receptor binding	+	0.5586	55.86%
Androgen receptor binding	-	0.6384	63.84%
Thyroid receptor binding	-	0.5580	55.80%
Glucocorticoid receptor binding	+	0.5453	54.53%
Aromatase binding	-	0.5052	50.52%
PPAR gamma	+	0.6059	60.59%
Honey bee toxicity	-	0.8312	83.12%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	+	0.7739	77.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.01%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.71%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.57%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.45%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.41%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.24%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.93%	96.00%
CHEMBL4208	P20618	Proteasome component C5	83.77%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.03%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.81%	95.56%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.61%	82.50%
CHEMBL3194	P02766	Transthyretin	82.34%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.07%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.35%	96.95%

Plants that contains it

• Alkanna cappadocica
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Crambe tatarica
• Diospyros eriantha
• Fritillaria monantha
• Hoffmannia strigillosa
• Humulus lupulus
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Pteris semipinnata
• Salvia hispanica
• Scorzonera pseudodivaricata
• Stenocereus griseus
• Syncarpia hillii

Cross-Links

• PubChem: 11566620
• NPASS: NPC106025
• ChEMBL: CHEMBL456751
• LOTUS: LTS0242591
• wikiData: Q105214085