8-[(6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]-1-hydroxy-3-methoxy-6-methylanthraquinone

Details

• Internal ID: 9073391f-05ae-41b4-9cc8-d961bb1bcc35
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-hydroxy-3-methoxy-6-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)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)C(=O)C5=C(C2=O)C=C(C=C5O)OC
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)C(=O)C5=C(C2=O)C=C(C=C5O)OC
• InChI: InChI=1S/C28H32O15/c1-9-3-11-18(22(34)17-12(19(11)31)5-10(39-2)6-13(17)30)14(4-9)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: LHWONDXFTUKXDH-BFTLVBKUSA-N
• Popularity: 0 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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7316	73.16%
Caco-2	-	0.8939	89.39%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4633	46.33%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8765	87.65%
OATP1B3 inhibitior	+	0.9776	97.76%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5124	51.24%
P-glycoprotein inhibitior	-	0.5633	56.33%
P-glycoprotein substrate	-	0.8153	81.53%
CYP3A4 substrate	+	0.6130	61.30%
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	+	0.4553	45.53%
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	-	0.9252	92.52%
Skin irritation	-	0.8593	85.93%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	+	0.6408	64.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.4375	43.75%
Micronuclear	+	0.5933	59.33%
Hepatotoxicity	-	0.6823	68.23%
skin sensitisation	-	0.9107	91.07%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7688	76.88%
Acute Oral Toxicity (c)	III	0.6709	67.09%
Estrogen receptor binding	+	0.8326	83.26%
Androgen receptor binding	-	0.5761	57.61%
Thyroid receptor binding	-	0.5361	53.61%
Glucocorticoid receptor binding	+	0.5613	56.13%
Aromatase binding	+	0.6227	62.27%
PPAR gamma	+	0.7230	72.30%
Honey bee toxicity	-	0.7852	78.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7401	74.01%

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	98.26%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.53%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.63%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.99%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.49%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.74%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.53%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.45%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	93.37%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.06%	99.15%
CHEMBL226	P30542	Adenosine A1 receptor	90.75%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.36%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.31%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.71%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.61%	99.17%
CHEMBL4208	P20618	Proteasome component C5	86.71%	90.00%
CHEMBL4581	P52732	Kinesin-like protein 1	85.67%	93.18%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.26%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.16%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.93%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.36%	96.90%

Plants that contains it

• Albizia myriophylla
• Amphorogyne spicata
• Anaphalis lactea
• Anchusa azurea
• Balanophora laxiflora
• Benincasa hispida
• Carduus tenuiflorus
• Chaiturus marrubiastrum
• Chamaecrista glandulosa var. glandulosa
• Cryptochilus strictus
• Degenia velebitica
• Delphinium nuttallianum
• Delphinium virgatum
• Dillenia indica
• Dipsacus dipsacoides
• Erythrophleum ivorense
• Grangea maderaspatana
• Helichrysum chionosphaerum
• Jacquemontia paniculata
• Leptocereus quadricostatus
• Lespedeza tomentosa
• Lupinus argenteus subsp. argenteus
• Lycium barbarum
• Lycium chinense
• Mandragora officinarum
• Metrodorea nigra
• Nepeta granatensis
• Onobrychis arenaria
• Petunia inflata
• Phedimus selskanianus
• Photinia serratifolia
• Pittocaulon praecox
• Quercus rubra
• Rheum australe
• Rheum officinale
• Rheum palmatum
• Rosa villosa
• Salvia greggii
• Senecio behnii
• Senna obtusifolia
• Sticherus quadripartitus
• Tagetes filifolia
• Tanacetum coccineum
• Verbascum densiflorum

Cross-Links

• PubChem: 5320543
• NPASS: NPC232189
• LOTUS: LTS0224773
• wikiData: Q105152023