Physcion 8-gentiobioside

Details

• Internal ID: 4eca085a-e949-4496-9973-f773fd49359e
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-hydroxy-6-methoxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-9,10-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)OC
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)OC
• InChI: InChI=1S/C28H32O15/c1-9-3-11-17(13(30)4-9)22(34)18-12(19(11)31)5-10(39-2)6-14(18)41-28-26(38)24(36)21(33)16(43-28)8-40-27-25(37)23(35)20(32)15(7-29)42-27/h3-6,15-16,20-21,23-30,32-33,35-38H,7-8H2,1-2H3/t15-,16-,20-,21-,23+,24+,25-,26-,27-,28-/m1/s1
• InChI Key: YMXXCMGLMRYEQD-BFTLVBKUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.51
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• Physcion diglucoside
• Physcion-8-O-|A-gentiobioside
• CHEMBL3634702
• Physcion 8-O-beta-D-gentiobioside
• 84268-38-2
• Physcion-beta-D-gentiobioside
• 1-hydroxy-6-methoxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-9,10-dione
• SCHEMBL4743854
• CHEBI:27598
• BDBM50133036
• HY-N10371
• LMPK13040012
• PHYSCION-8-O-BETA-GENTIOBIOSIDE
• CS-0435550
• E89004
• Q27103214
• 8-hydroxy-3-methoxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7316	73.16%
Caco-2	-	0.8921	89.21%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4633	46.33%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.8759	87.59%
OATP1B3 inhibitior	+	0.9776	97.76%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6032	60.32%
P-glycoprotein inhibitior	-	0.5733	57.33%
P-glycoprotein substrate	-	0.8178	81.78%
CYP3A4 substrate	+	0.6103	61.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	-	0.9311	93.11%
CYP2C9 inhibition	-	0.9167	91.67%
CYP2C19 inhibition	-	0.9109	91.09%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.9167	91.67%
CYP2C8 inhibition	-	0.6141	61.41%
CYP inhibitory promiscuity	-	0.8842	88.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7120	71.20%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9215	92.15%
Skin irritation	-	0.8593	85.93%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	+	0.6708	67.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.3817	38.17%
Micronuclear	+	0.5933	59.33%
Hepatotoxicity	-	0.6573	65.73%
skin sensitisation	-	0.9107	91.07%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7044	70.44%
Acute Oral Toxicity (c)	III	0.6709	67.09%
Estrogen receptor binding	+	0.8394	83.94%
Androgen receptor binding	-	0.5761	57.61%
Thyroid receptor binding	-	0.5140	51.40%
Glucocorticoid receptor binding	+	0.5401	54.01%
Aromatase binding	+	0.6225	62.25%
PPAR gamma	+	0.7198	71.98%
Honey bee toxicity	-	0.8017	80.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.7401	74.01%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2409	P34913	Epoxide hydratase	40600 nM	IC50	PMID: 26483136

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.80%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.50%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.42%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.17%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.06%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.48%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.38%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.14%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	92.55%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.84%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.56%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.88%	86.92%
CHEMBL4208	P20618	Proteasome component C5	87.64%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.93%	97.36%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.14%	96.00%
CHEMBL4581	P52732	Kinesin-like protein 1	85.37%	93.18%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.18%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.13%	86.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.94%	96.90%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.53%	99.17%

Plants that contains it

• Chamaecrista glandulosa var. glandulosa
• Reynoutria multiflora
• Rhamnus virgata
• Rheum australe
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Senna obtusifolia
• Senna tora

Cross-Links

• PubChem: 442762
• NPASS: NPC46958
• ChEMBL: CHEMBL3634702
• LOTUS: LTS0149645
• wikiData: Q27103214