Loroglossin

Details

• Internal ID: dc737286-7daa-43f6-8bee-31b76dc0fabc
• 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,3S)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate
• SMILES (Canonical): CC(C)CC(C(C(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)O)(C(=O)OCC3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): CC(C)C[C@@]([C@@H](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(=O)OCC3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C34H46O18/c1-16(2)11-34(46,33(45)48-15-18-5-9-20(10-6-18)50-32-28(42)26(40)24(38)22(13-36)52-32)29(43)30(44)47-14-17-3-7-19(8-4-17)49-31-27(41)25(39)23(37)21(12-35)51-31/h3-10,16,21-29,31-32,35-43,46H,11-15H2,1-2H3/t21-,22-,23-,24-,25+,26+,27-,28-,29-,31-,32-,34-/m1/s1
• InChI Key: QABASLXUKXNHMC-PIFIRMJRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₆O₁₈
• Molecular Weight: 742.70 g/mol
• Exact Mass: 742.26841461 g/mol
• Topological Polar Surface Area (TPSA): 292.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -3.03
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 15

Synonyms

• 58139-22-3
• Loroglossine
• MEGxp0_001354
• CHEMBL4873128
• ACon1_001456
• DTXSID40973709
• AKOS040762971
• NCGC00180487-01
• bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R,3S)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate
• BRD-K30768645-001-01-0
• Bis{[4-(hexopyranosyloxy)phenyl]methyl} 2,3-dihydroxy-2-(2-methylpropyl)butanedioate
• beta-D-Glucopyranoside, ((2R,3S)-2,3-dihydroxy-2-(2-methylpropyl)-1,4-dioxo-1,4-butanediyl)bis(oxymethylene-4,1-phenylene) bis-
• bis(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl) (2R,3S)-2,3-dihydroxy-2-isobutylsuccinate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7084	70.84%
Caco-2	-	0.8668	86.68%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7809	78.09%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8980	89.80%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7591	75.91%
P-glycoprotein inhibitior	+	0.7231	72.31%
P-glycoprotein substrate	-	0.8234	82.34%
CYP3A4 substrate	+	0.6114	61.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8814	88.14%
CYP3A4 inhibition	-	0.9062	90.62%
CYP2C9 inhibition	-	0.8914	89.14%
CYP2C19 inhibition	-	0.9324	93.24%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9031	90.31%
CYP2C8 inhibition	-	0.5904	59.04%
CYP inhibitory promiscuity	-	0.9670	96.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6647	66.47%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9065	90.65%
Skin irritation	-	0.8623	86.23%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7135	71.35%
Micronuclear	-	0.6626	66.26%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8767	87.67%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8642	86.42%
Acute Oral Toxicity (c)	III	0.7004	70.04%
Estrogen receptor binding	+	0.7165	71.65%
Androgen receptor binding	+	0.7080	70.80%
Thyroid receptor binding	+	0.5438	54.38%
Glucocorticoid receptor binding	+	0.6680	66.80%
Aromatase binding	+	0.5251	52.51%
PPAR gamma	+	0.6840	68.40%
Honey bee toxicity	-	0.8062	80.62%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9275	92.75%

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	98.41%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.58%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.49%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.81%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.11%	97.25%
CHEMBL2179	P04062	Beta-glucocerebrosidase	90.44%	85.31%
CHEMBL3401	O75469	Pregnane X receptor	89.37%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.88%	97.09%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.15%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.07%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.05%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.13%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.86%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.73%	96.00%
CHEMBL4208	P20618	Proteasome component C5	81.29%	90.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.64%	94.97%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.49%	89.67%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.38%	86.92%

Plants that contains it

• Cremastra appendiculata
• Dactylorhiza hatagirea
• Gymnadenia conopsea
• Pleione bulbocodioides
• Pleione yunnanensis

Cross-Links

• PubChem: 185907
• NPASS: NPC248119
• LOTUS: LTS0276437
• wikiData: Q82957739