[(1S,2S,4S,5S,6R,10S)-5-hydroxy-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-2-yl]methyl benzoate

Details

• Internal ID: 512162f8-716d-4ff7-83aa-f40ffffb88a1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(1S,2S,4S,5S,6R,10S)-5-hydroxy-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-2-yl]methyl benzoate
• SMILES (Canonical): C1=CC=C(C=C1)C(=O)OCC23C4C(C=COC4OC5C(C(C(C(O5)CO)O)O)O)C(C2O3)O
• SMILES (Isomeric): C1=CC=C(C=C1)C(=O)OC[C@@]23[C@@H]4[C@@H](C=CO[C@H]4O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)[C@@H]([C@@H]2O3)O
• InChI: InChI=1S/C22H26O11/c23-8-12-15(25)16(26)17(27)21(31-12)32-20-13-11(6-7-29-20)14(24)18-22(13,33-18)9-30-19(28)10-4-2-1-3-5-10/h1-7,11-18,20-21,23-27H,8-9H2/t11-,12-,13-,14+,15-,16+,17-,18+,20+,21+,22-/m1/s1
• InChI Key: JADZPWILSJVZBO-LHBWGZIGSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₁₁
• Molecular Weight: 466.40 g/mol
• Exact Mass: 466.14751164 g/mol
• Topological Polar Surface Area (TPSA): 168.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.73
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• NCGC00180092-01
• BRD-K57930888-001-01-0
• [(1aS)-1abeta-[(Benzoyloxy)methyl]-6alpha-hydroxy-1a,1balpha,2,5aalpha,6,6abeta-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-2alpha-yl]beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5563	55.63%
Caco-2	-	0.8725	87.25%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6228	62.28%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8487	84.87%
OATP1B3 inhibitior	+	0.9549	95.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6651	66.51%
P-glycoprotein inhibitior	-	0.6856	68.56%
P-glycoprotein substrate	-	0.8022	80.22%
CYP3A4 substrate	+	0.6207	62.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8533	85.33%
CYP3A4 inhibition	-	0.9273	92.73%
CYP2C9 inhibition	-	0.9143	91.43%
CYP2C19 inhibition	-	0.7950	79.50%
CYP2D6 inhibition	-	0.8997	89.97%
CYP1A2 inhibition	-	0.8891	88.91%
CYP2C8 inhibition	+	0.6133	61.33%
CYP inhibitory promiscuity	-	0.8019	80.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5992	59.92%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9465	94.65%
Skin irritation	-	0.7852	78.52%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6409	64.09%
Micronuclear	-	0.5841	58.41%
Hepatotoxicity	-	0.8032	80.32%
skin sensitisation	-	0.8126	81.26%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7020	70.20%
Acute Oral Toxicity (c)	III	0.3987	39.87%
Estrogen receptor binding	+	0.6954	69.54%
Androgen receptor binding	+	0.5374	53.74%
Thyroid receptor binding	+	0.5179	51.79%
Glucocorticoid receptor binding	-	0.5895	58.95%
Aromatase binding	+	0.6710	67.10%
PPAR gamma	+	0.6954	69.54%
Honey bee toxicity	-	0.8107	81.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6955	69.55%
Fish aquatic toxicity	+	0.6646	66.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.52%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.41%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.63%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.23%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.88%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.18%	94.08%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.82%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	86.50%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.78%	96.61%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.77%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.42%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	83.63%	91.49%
CHEMBL5028	O14672	ADAM10	82.78%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.67%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.75%	99.17%

Plants that contains it

• Globularia bisnagarica
• Globularia davisiana
• Penstemon auriberbis
• Plantago patagonica
• Platycodon grandiflorus

Cross-Links

• PubChem: 23846544
• NPASS: NPC173368
• LOTUS: LTS0127376
• wikiData: Q105123700