Dactylorhin A

Details

• Internal ID: 49b77f29-fcc0-4d7e-8db9-de9584ec7c29
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R)-2-(2-methylpropyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanedioate
• SMILES (Canonical): CC(C)CC(CC(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)(C(=O)OCC3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): CC(C)C[C@@](CC(=O)OCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)(C(=O)OCC3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C40H56O22/c1-18(2)11-40(62-38-35(53)32(50)29(47)25(15-43)61-38,39(54)56-17-20-5-9-22(10-6-20)58-37-34(52)31(49)28(46)24(14-42)60-37)12-26(44)55-16-19-3-7-21(8-4-19)57-36-33(51)30(48)27(45)23(13-41)59-36/h3-10,18,23-25,27-38,41-43,45-53H,11-17H2,1-2H3/t23-,24-,25-,27-,28-,29-,30+,31+,32+,33-,34-,35-,36-,37-,38+,40-/m1/s1
• InChI Key: QUCKZYFUROTIBC-HDQVGPIMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₆O₂₂
• Molecular Weight: 888.90 g/mol
• Exact Mass: 888.32632341 g/mol
• Topological Polar Surface Area (TPSA): 351.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -4.18
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 18

Synonyms

• 256459-34-4
• DactylorhinA
• beta-D-Glucopyranoside, ((2R)-2-(beta-D-glucopyranosyloxy)-2-(2-methylpropyl)-1,4-dioxo-1,4-butanediyl)bis(oxymethylene-4,1-phenylene)bis-
• MEGxp0_001355
• CHEMBL4861038
• ACon1_001494
• DTXSID801346255
• AKOS040760359
• NCGC00180448-01
• MS-31654
• HY-125531
• CS-0092126
• BRD-K87894247-001-01-8
• bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R)-2-(2-methylpropyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanedioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7533	75.33%
Caco-2	-	0.8702	87.02%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8544	85.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.9078	90.78%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9281	92.81%
P-glycoprotein inhibitior	+	0.7320	73.20%
P-glycoprotein substrate	-	0.7808	78.08%
CYP3A4 substrate	+	0.6163	61.63%
CYP2C9 substrate	-	0.8096	80.96%
CYP2D6 substrate	-	0.8803	88.03%
CYP3A4 inhibition	-	0.7981	79.81%
CYP2C9 inhibition	-	0.8067	80.67%
CYP2C19 inhibition	-	0.8582	85.82%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.8755	87.55%
CYP2C8 inhibition	-	0.5886	58.86%
CYP inhibitory promiscuity	-	0.9354	93.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6376	63.76%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9060	90.60%
Skin irritation	-	0.8619	86.19%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7822	78.22%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8826	88.26%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7622	76.22%
Acute Oral Toxicity (c)	III	0.6532	65.32%
Estrogen receptor binding	+	0.7580	75.80%
Androgen receptor binding	+	0.6963	69.63%
Thyroid receptor binding	+	0.5674	56.74%
Glucocorticoid receptor binding	+	0.6829	68.29%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7303	73.03%
Honey bee toxicity	-	0.7419	74.19%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	+	0.9795	97.95%

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	98.21%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.27%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.46%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.17%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.49%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.40%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.07%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.52%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	86.79%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.57%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	85.83%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.82%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.13%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.58%	95.56%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.44%	85.31%
CHEMBL4208	P20618	Proteasome component C5	81.09%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.45%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.10%	86.33%

Plants that contains it

• Bletilla striata
• Cremastra appendiculata
• Dactylorhiza hatagirea
• Gymnadenia conopsea
• Pleione bulbocodioides
• Pleione yunnanensis
• Syzygium aromaticum

Cross-Links

• PubChem: 10819499
• NPASS: NPC169968
• LOTUS: LTS0187220
• wikiData: Q105228081