Osmanthuside H

Details

• Internal ID: 0108f1b1-666f-4da8-bf22-ac077fe2d5a2
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(O1)OCC2C(C(C(C(O2)OCCC3=CC=C(C=C3)O)O)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OCCC3=CC=C(C=C3)O)O)O)O)O)(CO)O
• InChI: InChI=1S/C19H28O11/c20-8-19(26)9-29-18(16(19)25)28-7-12-13(22)14(23)15(24)17(30-12)27-6-5-10-1-3-11(21)4-2-10/h1-4,12-18,20-26H,5-9H2/t12-,13-,14+,15-,16+,17-,18-,19-/m1/s1
• InChI Key: IVRQZYXJBVMHCW-OTCFHACESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₁₁
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.16316171 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.78
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 149155-70-4
• (2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol
• 2-(4-Hydroxyphenyl)ethyl-beta-D-apiosyl-(1-6)-beta-D-glucopyranoside
• MEGxp0_000044
• ACon1_001497
• DTXSID60933562
• AKOS040735759
• NCGC00180444-01
• Osmanthuside H, >=95% (LC/MS-ELSD)
• 2-(4-Hydroxyphenyl)ethyl 6-O-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7901	79.01%
Caco-2	-	0.8273	82.73%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7813	78.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8937	89.37%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7624	76.24%
P-glycoprotein inhibitior	-	0.7753	77.53%
P-glycoprotein substrate	-	0.7194	71.94%
CYP3A4 substrate	+	0.6105	61.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8058	80.58%
CYP3A4 inhibition	-	0.9087	90.87%
CYP2C9 inhibition	-	0.8654	86.54%
CYP2C19 inhibition	-	0.8415	84.15%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	-	0.9133	91.33%
CYP2C8 inhibition	+	0.6694	66.94%
CYP inhibitory promiscuity	-	0.8761	87.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5485	54.85%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9185	91.85%
Skin irritation	-	0.8122	81.22%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6658	66.58%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8829	88.29%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.7080	70.80%
Acute Oral Toxicity (c)	III	0.5994	59.94%
Estrogen receptor binding	+	0.7288	72.88%
Androgen receptor binding	-	0.5160	51.60%
Thyroid receptor binding	+	0.6669	66.69%
Glucocorticoid receptor binding	+	0.5769	57.69%
Aromatase binding	+	0.8057	80.57%
PPAR gamma	+	0.7833	78.33%
Honey bee toxicity	-	0.7331	73.31%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	-	0.6204	62.04%

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	98.68%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	96.62%	94.62%
CHEMBL226	P30542	Adenosine A1 receptor	96.15%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.28%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.12%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.34%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.09%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.49%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.87%	86.92%
CHEMBL2581	P07339	Cathepsin D	86.67%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.52%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.16%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.64%	95.89%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.39%	94.97%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.36%	96.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.65%	94.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.66%	92.94%
CHEMBL242	Q92731	Estrogen receptor beta	80.55%	98.35%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.49%	85.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.14%	94.00%

Plants that contains it

• Holmskioldia sanguinea
• Ipomoea nil
• Ipomoea purpurea
• Ligustrum lucidum
• Miliusa balansae
• Phellodendron amurense
• Sargentodoxa cuneata

Cross-Links

• PubChem: 192437
• NPASS: NPC60814
• LOTUS: LTS0242435
• wikiData: Q76084642