(-)-Specioside

Details

• Internal ID: 3bc728a5-9784-4939-a3d8-3f5216840bd8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1S,2R,4S,5S,6R,10S)-2-(hydroxymethyl)-5-[(E)-2-(4-hydroxyphenyl)ethenoxy]-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]oxane-3,4,5-triol
• InChI: InChI=1S/C23H28O11/c24-9-14-16(27)17(28)18(29)22(32-14)33-21-15-13(6-8-31-21)19(20-23(15,10-25)34-20)30-7-5-11-1-3-12(26)4-2-11/h1-8,13-22,24-29H,9-10H2/b7-5+/t13-,14-,15-,16-,17+,18-,19+,20+,21+,22+,23+/m1/s1
• InChI Key: AWKRVVGAVDYMNU-XKVKTCGNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₁
• Molecular Weight: 480.50 g/mol
• Exact Mass: 480.16316171 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.19
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• (1S,2S,4S,5S,6S,10S)-2-(Hydroxymethyl)-10-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-3,9-dioxatricyclo(4.4.0.0,)dec-7-en-5-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
• (1S,2S,4S,5S,6S,10S)-2-(Hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0,]dec-7-en-5-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(((1S,2R,4S,5S,6R,10S)-2-(hydroxymethyl)-5-((E)-2-(4-hydroxyphenyl)ethenoxy)-3,9-dioxatricyclo(4.4.0.02,4)dec-7-en-10-yl)oxy)oxane-3,4,5-triol
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1S,2R,4S,5S,6R,10S)-2-(hydroxymethyl)-5-[(E)-2-(4-hydroxyphenyl)ethenoxy]-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]oxane-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-(((1aR,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-6-((E)-2-(4-hydroxyphenyl)ethenoxy)-2,5a,6,6a-tetrahydro-1bH-oxireno(5,6)cyclopenta(1,3-c)pyran-2-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-[[(1aR,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-6-[(E)-2-(4-hydroxyphenyl)ethenoxy]-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• RefChem:67953
• CHEMBL516849
• BDBM50250503

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5563	55.63%
Caco-2	-	0.8800	88.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5386	53.86%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8171	81.71%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7835	78.35%
P-glycoprotein inhibitior	-	0.6972	69.72%
P-glycoprotein substrate	-	0.6825	68.25%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	0.8091	80.91%
CYP2D6 substrate	-	0.8258	82.58%
CYP3A4 inhibition	-	0.9293	92.93%
CYP2C9 inhibition	-	0.8849	88.49%
CYP2C19 inhibition	-	0.7029	70.29%
CYP2D6 inhibition	-	0.8622	86.22%
CYP1A2 inhibition	-	0.8613	86.13%
CYP2C8 inhibition	+	0.6718	67.18%
CYP inhibitory promiscuity	-	0.7137	71.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4921	49.21%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9423	94.23%
Skin irritation	-	0.7689	76.89%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7043	70.43%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	-	0.8675	86.75%
skin sensitisation	-	0.7950	79.50%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4434	44.34%
Estrogen receptor binding	+	0.6888	68.88%
Androgen receptor binding	+	0.5845	58.45%
Thyroid receptor binding	+	0.5955	59.55%
Glucocorticoid receptor binding	-	0.6010	60.10%
Aromatase binding	+	0.7555	75.55%
PPAR gamma	+	0.7648	76.48%
Honey bee toxicity	-	0.7036	70.36%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.6795	67.95%

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	99.13%	91.11%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	94.05%	89.67%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	91.13%	94.23%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.41%	83.57%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.02%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.94%	86.33%
CHEMBL242	Q92731	Estrogen receptor beta	88.81%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.57%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.87%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.57%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.94%	97.09%
CHEMBL3194	P02766	Transthyretin	86.41%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	85.23%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.93%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.69%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	84.28%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.06%	86.92%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.02%	94.97%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.51%	94.45%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.37%	90.93%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.15%	97.28%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.02%	91.38%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 44566579
• LOTUS: LTS0266086
• wikiData: Q104920099