2,5-dihydroxy-6-[(E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-enylidene]-2,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]cyclohex-4-ene-1,3-dione

Details

• Internal ID: 704a84ce-b7ac-4df2-a4d8-369abffaf263
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: 2,5-dihydroxy-6-[(E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-enylidene]-2,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]cyclohex-4-ene-1,3-dione
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=C2C(=C(C(=O)C(C2=O)(O)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=C2C(=C(C(=O)C(C2=O)(O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C27H32O18/c28-7-12-15(32)18(35)20(37)25(42-12)44-22-17(34)14(11(31)6-3-9-1-4-10(30)5-2-9)23(39)27(41,24(22)40)45-26-21(38)19(36)16(33)13(8-29)43-26/h1-6,12-13,15-16,18-21,25-26,28-38,41H,7-8H2/b6-3+,14-11?/t12-,13-,15-,16-,18+,19+,20-,21-,25+,26+,27?/m1/s1
• InChI Key: BQKAMCSHYODWLH-GULDIDOESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₈
• Molecular Weight: 644.50 g/mol
• Exact Mass: 644.15886417 g/mol
• Topological Polar Surface Area (TPSA): 314.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -4.54
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8469	84.69%
Caco-2	-	0.9131	91.31%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6837	68.37%
OATP2B1 inhibitior	-	0.7059	70.59%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4718	47.18%
P-glycoprotein inhibitior	-	0.4856	48.56%
P-glycoprotein substrate	-	0.8552	85.52%
CYP3A4 substrate	+	0.6149	61.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	-	0.9376	93.76%
CYP2C9 inhibition	-	0.8110	81.10%
CYP2C19 inhibition	-	0.8116	81.16%
CYP2D6 inhibition	-	0.9240	92.40%
CYP1A2 inhibition	-	0.9242	92.42%
CYP2C8 inhibition	+	0.6928	69.28%
CYP inhibitory promiscuity	-	0.8056	80.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6483	64.83%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8965	89.65%
Skin irritation	-	0.8252	82.52%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.6024	60.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8037	80.37%
Micronuclear	-	0.5667	56.67%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.7968	79.68%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6464	64.64%
Acute Oral Toxicity (c)	III	0.5183	51.83%
Estrogen receptor binding	+	0.7626	76.26%
Androgen receptor binding	+	0.6638	66.38%
Thyroid receptor binding	-	0.5341	53.41%
Glucocorticoid receptor binding	-	0.5812	58.12%
Aromatase binding	+	0.6000	60.00%
PPAR gamma	+	0.6671	66.71%
Honey bee toxicity	-	0.7691	76.91%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8307	83.07%

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	99.18%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.87%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.59%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	94.45%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.16%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.07%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.06%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.32%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.81%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.42%	91.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.45%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.35%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	85.06%	94.75%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.71%	89.67%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.61%	86.92%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.39%	88.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.37%	95.83%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.06%	97.33%

Plants that contains it

• Carthamus tinctorius

Cross-Links

• PubChem: 102200539
• NPASS: NPC310775