Daphnin

Details

• Internal ID: dc7da701-12b1-4999-aeeb-5e889685d6ba
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 8-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): C1=CC(=C(C2=C1C=CC(=O)O2)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CC(=C(C2=C1C=CC(=O)O2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C15H16O9/c16-5-8-10(18)12(20)13(21)15(23-8)22-7-3-1-6-2-4-9(17)24-14(6)11(7)19/h1-4,8,10,12-13,15-16,18-21H,5H2/t8-,10-,12+,13-,15-/m1/s1
• InChI Key: HOIXTKAYCMNVMY-PVOAASPHSA-N
• Popularity: 11 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

• 486-55-5
• Daphnoside
• UNII-K4REW3G17G
• K4REW3G17G
• 8-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• CHEBI:17989
• 7-(beta-D-glucopyranosyloxy)-8-hydroxycoumarin
• 8-hydroxy-2-oxo-2H-chromen-7-yl beta-D-glucopyranoside
• 7-(beta-D-glucopyranosyloxy)-8-hydroxy-2H-chromen-2-one
• 7-(beta-D-Glucopyranosyloxy)-8-hydroxy-2H-1-benzopyran-2-one
• 8-Hydroxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-2-one
• DAPHNIN [MI]
• MLS002472875
• SCHEMBL127932
• CHEMBL1879316
• DTXSID80197563
• HMS2197N06
• HY-N7252
• 7-GLUCOSIDO-8-HYDROXYCOUMARIN
• AKOS040732922
• DAPHNETIN 7-.BETA.-D-GLUCOSIDE
• NCGC00160173-01
• 7,8-dihydroxycoumarin 7-beta-D-glucoside
• MS-25182
• SMR000156204
• CS-0110795
• C01421
• 7,8-DIHYDROXYCOUMARIN 7-.BETA.-D-GLUCOSIDE
• Q5221745
• 7-beta-(D-Glucopyranosyloxy)-8-hydroxy-2H-1-benzopyran-2-one
• 2H-1-Benzopyran-2-one, 7-(beta-D-glucopyranosyloxy)-8-hydroxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5923	59.23%
Caco-2	-	0.9307	93.07%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5362	53.62%
OATP2B1 inhibitior	-	0.5582	55.82%
OATP1B1 inhibitior	+	0.9009	90.09%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9392	93.92%
P-glycoprotein inhibitior	-	0.9329	93.29%
P-glycoprotein substrate	-	0.9392	93.92%
CYP3A4 substrate	-	0.5397	53.97%
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	-	0.6317	63.17%
CYP inhibitory promiscuity	-	0.8472	84.72%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7090	70.90%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.7707	77.07%
Skin irritation	-	0.7983	79.83%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7727	77.27%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8796	87.96%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7512	75.12%
Acute Oral Toxicity (c)	III	0.4513	45.13%
Estrogen receptor binding	-	0.4934	49.34%
Androgen receptor binding	+	0.5340	53.40%
Thyroid receptor binding	-	0.5316	53.16%
Glucocorticoid receptor binding	+	0.6728	67.28%
Aromatase binding	+	0.6814	68.14%
PPAR gamma	+	0.6214	62.14%
Honey bee toxicity	-	0.8637	86.37%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7699	76.99%
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	94.20%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.32%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.85%	83.57%
CHEMBL2581	P07339	Cathepsin D	88.30%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	84.22%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.80%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.66%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	81.39%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.00%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.63%	99.23%

Plants that contains it

• Acer caudatifolium
• Aconitum heterophyllum
• Astragalus sinicus
• Baccharis macraei
• Cruciata pedemontana
• Cynoglossum lanceolatum
• Daphnandra dielsii
• Daphnandra repandula
• Daphne acutiloba
• Daphne arisanensis
• Daphne feddei
• Daphne gnidioides
• Daphne gnidium
• Daphne odora
• Daphne oleoides
• Daphne sericea
• Derris reticulata
• Eucalyptus ovata
• Gentiana arisanensis
• Klasea centauroides subsp. strangulata
• Leucoptera nodosa
• Lindera glauca
• Marshallia graminifolia
• Mikania goyazensis
• Oxytropis ochrocephala
• Panzerina lanata
• Polytrichastrum formosum
• Rumohra adiantiformis
• Salacia cordata
• Solanum aculeatissimum
• Solanum dulcamara
• Stellera chamaejasme
• Stenocephalum megapotamicum
• Syzygium sandwicense

Cross-Links

• PubChem: 439499
• NPASS: NPC41844
• LOTUS: LTS0215854
• wikiData: Q5221745