Datiscin

Details

• Internal ID: ede89dcb-ad2c-48c9-a872-53771d28e87c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(2-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=CC=C5O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=CC=C5O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-10(28)7-14(16)40-24(25)11-4-2-3-5-12(11)29/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
• InChI Key: BJJCTXDEJUWVIC-QHWHWDPRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• 16310-92-2
• datiscetin-3-rutinose
• CHEMBL444402
• AKOS040761574
• Q63392116
• 5,7-dihydroxy-2-(2-hydroxyphenyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5564	55.64%
Caco-2	-	0.9242	92.42%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7477	74.77%
OATP2B1 inhibitior	-	0.5617	56.17%
OATP1B1 inhibitior	+	0.8185	81.85%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5922	59.22%
P-glycoprotein inhibitior	-	0.6150	61.50%
P-glycoprotein substrate	+	0.5448	54.48%
CYP3A4 substrate	+	0.6462	64.62%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.8673	86.73%
CYP2C8 inhibition	+	0.7817	78.17%
CYP inhibitory promiscuity	-	0.6787	67.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9086	90.86%
Skin irritation	-	0.8089	80.89%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4172	41.72%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.9325	93.25%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8415	84.15%
Acute Oral Toxicity (c)	III	0.5971	59.71%
Estrogen receptor binding	+	0.8090	80.90%
Androgen receptor binding	+	0.6368	63.68%
Thyroid receptor binding	+	0.5517	55.17%
Glucocorticoid receptor binding	+	0.6285	62.85%
Aromatase binding	+	0.6685	66.85%
PPAR gamma	+	0.7329	73.29%
Honey bee toxicity	-	0.7880	78.80%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8993	89.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.70%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.38%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.65%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.09%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.98%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	94.83%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.46%	95.56%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.15%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.56%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.08%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.63%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.83%	99.23%
CHEMBL3194	P02766	Transthyretin	83.64%	90.71%
CHEMBL4208	P20618	Proteasome component C5	83.15%	90.00%
CHEMBL2535	P11166	Glucose transporter	82.97%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.45%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.42%	80.78%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.62%	93.65%

Plants that contains it

• Datisca cannabina

Cross-Links

• PubChem: 10054207
• LOTUS: LTS0130994
• wikiData: Q63392116