(2S,3S)-6-(2-hydroxyethyl)-2,5,7-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroinden-1-one

Details

• Internal ID: 8cc83299-4141-4d8e-a8d1-e0b7f4e93ed2
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2S,3S)-6-(2-hydroxyethyl)-2,5,7-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroinden-1-one
• SMILES (Canonical): CC1C(C2=C(C1=O)C(=C(C(=C2)C)CCO)C)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H](C2=C(C1=O)C(=C(C(=C2)C)CCO)C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C20H28O8/c1-8-6-12-14(9(2)11(8)4-5-21)15(23)10(3)19(12)28-20-18(26)17(25)16(24)13(7-22)27-20/h6,10,13,16-22,24-26H,4-5,7H2,1-3H3/t10-,13-,16-,17+,18-,19+,20+/m1/s1
• InChI Key: GTPYMQNYDRMGEN-ZBVSVKGWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₈
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.17841785 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.47
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5746	57.46%
Caco-2	-	0.8226	82.26%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6394	63.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7874	78.74%
OATP1B3 inhibitior	+	0.9338	93.38%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6583	65.83%
P-glycoprotein inhibitior	-	0.7877	78.77%
P-glycoprotein substrate	-	0.8235	82.35%
CYP3A4 substrate	+	0.5807	58.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.9019	90.19%
CYP2C9 inhibition	-	0.9010	90.10%
CYP2C19 inhibition	-	0.8918	89.18%
CYP2D6 inhibition	-	0.9360	93.60%
CYP1A2 inhibition	-	0.6860	68.60%
CYP2C8 inhibition	-	0.6670	66.70%
CYP inhibitory promiscuity	-	0.9094	90.94%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7515	75.15%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9548	95.48%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9007	90.07%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4682	46.82%
Acute Oral Toxicity (c)	III	0.5992	59.92%
Estrogen receptor binding	+	0.6634	66.34%
Androgen receptor binding	-	0.4860	48.60%
Thyroid receptor binding	-	0.4874	48.74%
Glucocorticoid receptor binding	+	0.6345	63.45%
Aromatase binding	-	0.5470	54.70%
PPAR gamma	-	0.5597	55.97%
Honey bee toxicity	-	0.8405	84.05%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4030	40.30%

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	96.89%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.20%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.96%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.39%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.19%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.59%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.42%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.67%	94.00%
CHEMBL4581	P52732	Kinesin-like protein 1	81.82%	93.18%

Plants that contains it

• Artemisia lactiflora
• Attalea phalerata
• Catalpa ovata
• Citrus medica
• Crepidiastrum sonchifolium
• Dipsacus inermis
• Duguetia calycina
• Garcinia pyrifera
• Greenwayodendron oliveri
• Jacaranda mimosifolia
• Microlepia strigosa
• Onychium japonicum
• Ophryosporus floribundus
• Payena lucida
• Phalaris canariensis
• Philotheca spicata
• Plumbagella micrantha
• Pteridium aquilinum
• Pteris bella
• Pteris multifida
• Pteris semipinnata
• Quassia indica
• Rivina humilis
• Swietenia mahagoni

Cross-Links

• PubChem: 23260007
• NPASS: NPC104287
• LOTUS: LTS0274393
• wikiData: Q105019252