(3r)-5-Methyl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]hexanoic acid

Details

• Internal ID: c1439f8e-afaf-4238-b83b-3b86f78889a1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (3R)-5-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]hexanoic acid
• SMILES (Canonical): CC(C)CC(CC(=O)O)(C(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC(C)C[C@@](CC(=O)O)(C(=O)OCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C27H40O16/c1-12(2)7-27(8-17(30)31,43-25-23(37)21(35)19(33)16(10-29)42-25)26(38)39-11-13-3-5-14(6-4-13)40-24-22(36)20(34)18(32)15(9-28)41-24/h3-6,12,15-16,18-25,28-29,32-37H,7-11H2,1-2H3,(H,30,31)/t15-,16-,18-,19-,20+,21+,22-,23-,24-,25+,27-/m1/s1
• InChI Key: ZGNUJHGCJSHIQU-JOOANJHQSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₁₆
• Molecular Weight: 620.60 g/mol
• Exact Mass: 620.23163518 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -3.02
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 13

Synonyms

• (3r)-5-methyl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]hexanoic acid
• CHEMBL4869805
• CHEBI:183887
• Dactylorhin E, >=95% (LC/MS-ELSD)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7074	70.74%
Caco-2	-	0.8882	88.82%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7712	77.12%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9044	90.44%
OATP1B3 inhibitior	+	0.9096	90.96%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5815	58.15%
P-glycoprotein inhibitior	-	0.4441	44.41%
P-glycoprotein substrate	-	0.8232	82.32%
CYP3A4 substrate	+	0.5912	59.12%
CYP2C9 substrate	-	0.6056	60.56%
CYP2D6 substrate	-	0.8834	88.34%
CYP3A4 inhibition	-	0.8531	85.31%
CYP2C9 inhibition	-	0.8485	84.85%
CYP2C19 inhibition	-	0.9164	91.64%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	-	0.8776	87.76%
CYP2C8 inhibition	-	0.6272	62.72%
CYP inhibitory promiscuity	-	0.9631	96.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6550	65.50%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9278	92.78%
Skin irritation	-	0.8439	84.39%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7239	72.39%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8661	86.61%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8375	83.75%
Acute Oral Toxicity (c)	III	0.6953	69.53%
Estrogen receptor binding	+	0.7251	72.51%
Androgen receptor binding	+	0.6392	63.92%
Thyroid receptor binding	-	0.5267	52.67%
Glucocorticoid receptor binding	+	0.5933	59.33%
Aromatase binding	+	0.5639	56.39%
PPAR gamma	+	0.5766	57.66%
Honey bee toxicity	-	0.7731	77.31%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7550	75.50%
Fish aquatic toxicity	+	0.8686	86.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.03%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.76%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.96%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.81%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.38%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.26%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.10%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.50%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	84.52%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.37%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.95%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.76%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.74%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.54%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.97%	94.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.87%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	80.69%	94.45%

Plants that contains it

• Bletilla striata
• Dactylorhiza hatagirea
• Gymnadenia conopsea
• Syzygium aromaticum

Cross-Links

• PubChem: 10555851
• NPASS: NPC68265
• LOTUS: LTS0143414
• wikiData: Q104401406