Daphneside

Details

• Internal ID: 7e8a4dc8-ee35-4f96-8a93-69cf3aafa4d9
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 7,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-2-one
• SMILES (Canonical): C1=CC(=C(C2=C1C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)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[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C21H26O14/c22-5-9-12(25)14(27)16(29)20(32-9)31-8-3-1-7-2-4-11(24)34-18(7)19(8)35-21-17(30)15(28)13(26)10(6-23)33-21/h1-4,9-10,12-17,20-23,25-30H,5-6H2/t9-,10-,12-,13-,14+,15+,16-,17-,20-,21+/m1/s1
• InChI Key: AWXQCKPVCRTEHJ-AJVLEMDISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₁₄
• Molecular Weight: 502.40 g/mol
• Exact Mass: 502.13225550 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -3.85
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• CHEMBL1209490

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6547	65.47%
Caco-2	-	0.8915	89.15%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5154	51.54%
OATP2B1 inhibitior	-	0.6989	69.89%
OATP1B1 inhibitior	+	0.9292	92.92%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7658	76.58%
P-glycoprotein inhibitior	-	0.7234	72.34%
P-glycoprotein substrate	-	0.9502	95.02%
CYP3A4 substrate	-	0.5492	54.92%
CYP2C9 substrate	-	0.8219	82.19%
CYP2D6 substrate	-	0.8584	85.84%
CYP3A4 inhibition	-	0.9408	94.08%
CYP2C9 inhibition	-	0.9449	94.49%
CYP2C19 inhibition	-	0.8867	88.67%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	-	0.9114	91.14%
CYP2C8 inhibition	-	0.7859	78.59%
CYP inhibitory promiscuity	-	0.8330	83.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6753	67.53%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9072	90.72%
Skin irritation	-	0.8240	82.40%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6576	65.76%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	+	0.5399	53.99%
skin sensitisation	-	0.8840	88.40%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5820	58.20%
Acute Oral Toxicity (c)	IV	0.4356	43.56%
Estrogen receptor binding	+	0.6636	66.36%
Androgen receptor binding	+	0.5810	58.10%
Thyroid receptor binding	+	0.5483	54.83%
Glucocorticoid receptor binding	+	0.5847	58.47%
Aromatase binding	+	0.6906	69.06%
PPAR gamma	+	0.5969	59.69%
Honey bee toxicity	-	0.8418	84.18%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7799	77.99%
Fish aquatic toxicity	+	0.7488	74.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.93%	94.00%
CHEMBL2581	P07339	Cathepsin D	85.88%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.72%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.64%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.28%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.05%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	81.29%	94.73%

Plants that contains it

• Daphne arisanensis
• Daphne oleoides
• Lawsonia inermis

Cross-Links

• PubChem: 15101829
• NPASS: NPC52740
• LOTUS: LTS0075724
• wikiData: Q104920355