7-hydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

Details

• Internal ID: 7da589e7-caed-4e79-99a8-b440f59a2e87
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 7-hydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): C1=CC(=C(C2=C1C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C2=C1C=CC(=O)O2)O[C@H]3[C@@H]([C@@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C15H16O9/c16-5-8-10(19)11(20)12(21)15(22-8)24-14-7(17)3-1-6-2-4-9(18)23-13(6)14/h1-4,8,10-12,15-17,19-21H,5H2/t8-,10-,11-,12-,15+/m1/s1
• InChI Key: MMPBHSBVPREJQC-WSWLIKMPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₉
• Molecular Weight: 340.28 g/mol
• Exact Mass: 340.07943208 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.32
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5923	59.23%
Caco-2	-	0.9262	92.62%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5362	53.62%
OATP2B1 inhibitior	-	0.5708	57.08%
OATP1B1 inhibitior	+	0.9185	91.85%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9475	94.75%
P-glycoprotein inhibitior	-	0.8926	89.26%
P-glycoprotein substrate	-	0.9635	96.35%
CYP3A4 substrate	-	0.5540	55.40%
CYP2C9 substrate	-	0.8141	81.41%
CYP2D6 substrate	-	0.8577	85.77%
CYP3A4 inhibition	-	0.9207	92.07%
CYP2C9 inhibition	-	0.9414	94.14%
CYP2C19 inhibition	-	0.9119	91.19%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.7995	79.95%
CYP inhibitory promiscuity	-	0.8472	84.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7090	70.90%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.6922	69.22%
Skin irritation	-	0.7983	79.83%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7520	75.20%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8796	87.96%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6500	65.00%
Acute Oral Toxicity (c)	III	0.4513	45.13%
Estrogen receptor binding	-	0.4886	48.86%
Androgen receptor binding	+	0.6202	62.02%
Thyroid receptor binding	-	0.5175	51.75%
Glucocorticoid receptor binding	+	0.7773	77.73%
Aromatase binding	-	0.5077	50.77%
PPAR gamma	+	0.6018	60.18%
Honey bee toxicity	-	0.8419	84.19%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7750	77.50%
Fish aquatic toxicity	+	0.7790	77.90%

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	98.20%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.20%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.80%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.90%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.46%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.29%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.00%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.69%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.70%	97.09%

Plants that contains it

• Astragalus pycnocephalus
• Coussarea paniculata
• Daphne feddei
• Hydrocotyle leucocephala
• Hymenocallis speciosa
• Ligularia pleurocaulis
• Lonchocarpus salvadorensis
• Ophioglossum petiolatum
• Oyedaea verbesinoides
• Pyrola calliantha
• Rhododendron lepidotum
• Solanum aculeatissimum
• Solanum berthaultii

Cross-Links

• PubChem: 22524175
• NPASS: NPC259150
• LOTUS: LTS0086991
• wikiData: Q105167953