Physcion 8-glucoside

Details

• Internal ID: 8ed4a310-090d-4586-928f-2c1395cf6c65
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-hydroxy-3-methoxy-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2=O)C=C(C=C4O)OC
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C4=C(C2=O)C=C(C=C4O)OC
• InChI: InChI=1S/C22H22O10/c1-8-3-10-16(19(27)15-11(17(10)25)5-9(30-2)6-12(15)24)13(4-8)31-22-21(29)20(28)18(26)14(7-23)32-22/h3-6,14,18,20-24,26,28-29H,7H2,1-2H3/t14-,18-,20+,21-,22-/m1/s1
• InChI Key: WLXGUTUUWXVZNM-DQMLXFRHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• Physcion 8-glucoside
• 1-Hydroxy-3-methoxy-6-methyl-8-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)anthracene-9,10-dione
• Physcion 1-O-beta-D-glucoside
• Physion 8-O-|A-D-glucoside
• Physion 8-O-beta-D-glucoside
• CHEBI:8185
• Physcion-1-O-beta-D-Glucopyranoside
• 1-hydroxy-3-methoxy-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• 9,10-Anthracenedione, 1-(beta-D-glucopyranosyloxy)-8-hydroxy-6-methoxy-3-methyl-
• Physcion-8-glucoside
• 9?10-Anthracenedione
• physcion 8-O-glucoside
• Physcion-8-beta-D-glucoside
• CHEMBL457944
• DTXSID30415749
• HY-N2107
• AKOS016010612
• AC-34142
• MS-28050
• CS-0018628
• F17662
• A877279
• Q27107882

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6138	61.38%
Caco-2	-	0.8270	82.70%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4839	48.39%
OATP2B1 inhibitior	-	0.5670	56.70%
OATP1B1 inhibitior	+	0.8912	89.12%
OATP1B3 inhibitior	+	0.9669	96.69%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6710	67.10%
P-glycoprotein inhibitior	-	0.6878	68.78%
P-glycoprotein substrate	-	0.8966	89.66%
CYP3A4 substrate	+	0.5854	58.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	-	0.8620	86.20%
CYP2C9 inhibition	-	0.8938	89.38%
CYP2C19 inhibition	-	0.9172	91.72%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.7915	79.15%
CYP2C8 inhibition	-	0.6296	62.96%
CYP inhibitory promiscuity	-	0.8575	85.75%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7544	75.44%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9064	90.64%
Skin irritation	-	0.8471	84.71%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	+	0.6808	68.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.5414	54.14%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.6698	66.98%
skin sensitisation	-	0.9250	92.50%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.7374	73.74%
Acute Oral Toxicity (c)	III	0.6506	65.06%
Estrogen receptor binding	+	0.6475	64.75%
Androgen receptor binding	-	0.5254	52.54%
Thyroid receptor binding	-	0.6323	63.23%
Glucocorticoid receptor binding	+	0.5858	58.58%
Aromatase binding	-	0.6232	62.32%
PPAR gamma	+	0.5486	54.86%
Honey bee toxicity	-	0.7983	79.83%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8091	80.91%

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	97.84%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.59%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.95%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	95.77%	96.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.44%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.18%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.13%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.03%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.51%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.54%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.62%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.99%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.34%	97.36%
CHEMBL4208	P20618	Proteasome component C5	87.30%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.76%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	85.20%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.93%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	81.10%	93.18%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.92%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.06%	97.14%

Plants that contains it

• Aconitum seravschanicum
• Adansonia grandidieri
• Alkekengi officinarum
• Aphyllocladus denticulatus
• Bassia muricata
• Dendriopoterium menendezii
• Dianthera secunda
• Dodonaea viscosa
• Dysoxylum cumingianum
• Enceliopsis argophylla
• Flacourtia jangomas
• Galatella sedifolia subsp. sedifolia
• Lavandula angustifolia subsp. pyrenaica
• Miliusa velutina
• Neobalanocarpus heimii
• Onobrychis arenaria
• Psychotria stachyoides
• Reynoutria japonica
• Reynoutria multiflora
• Rheum australe
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Senecio subdentatus
• Senna obtusifolia
• Teucrium yemense
• Trichotosia mollis

Cross-Links

• PubChem: 5319323
• NPASS: NPC30432
• LOTUS: LTS0274461
• wikiData: Q27107882