Fabiatrin

Details

• Internal ID: 5adbcc92-a925-48ef-840c-28ae4cc02d15
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)COC4C(C(C(CO4)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O)O)O)O
• InChI: InChI=1S/C21H26O13/c1-29-11-4-8-2-3-14(23)32-10(8)5-12(11)33-21-19(28)17(26)16(25)13(34-21)7-31-20-18(27)15(24)9(22)6-30-20/h2-5,9,13,15-22,24-28H,6-7H2,1H3/t9-,13-,15+,16-,17+,18-,19-,20+,21-/m1/s1
• InChI Key: AHBJPGDMGKOLJC-OJHUANBKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₁₃
• Molecular Weight: 486.40 g/mol
• Exact Mass: 486.13734088 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.56
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• 18309-73-4
• 6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one
• DTXSID501016106
• HY-N2285
• AKOS040760397
• CS-0019613
• 2H-1-Benzopyran-2-one, 6-methoxy-7-[(6-O-.beta.-D-xylopyranosyl-.beta.-D-glucopyranosyl)oxy]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8826	88.26%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5760	57.60%
OATP2B1 inhibitior	-	0.8482	84.82%
OATP1B1 inhibitior	+	0.8865	88.65%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4839	48.39%
P-glycoprotein inhibitior	-	0.7681	76.81%
P-glycoprotein substrate	-	0.5780	57.80%
CYP3A4 substrate	+	0.5752	57.52%
CYP2C9 substrate	-	0.8333	83.33%
CYP2D6 substrate	-	0.8474	84.74%
CYP3A4 inhibition	-	0.9272	92.72%
CYP2C9 inhibition	-	0.9606	96.06%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.8883	88.83%
CYP1A2 inhibition	-	0.8446	84.46%
CYP2C8 inhibition	-	0.6517	65.17%
CYP inhibitory promiscuity	-	0.9170	91.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6629	66.29%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9600	96.00%
Skin irritation	-	0.8272	82.72%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4137	41.37%
Micronuclear	+	0.5474	54.74%
Hepatotoxicity	-	0.7650	76.50%
skin sensitisation	-	0.8958	89.58%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9291	92.91%
Acute Oral Toxicity (c)	III	0.7019	70.19%
Estrogen receptor binding	+	0.7693	76.93%
Androgen receptor binding	-	0.5610	56.10%
Thyroid receptor binding	-	0.4937	49.37%
Glucocorticoid receptor binding	+	0.5592	55.92%
Aromatase binding	+	0.6432	64.32%
PPAR gamma	+	0.7101	71.01%
Honey bee toxicity	-	0.8618	86.18%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7149	71.49%
Fish aquatic toxicity	+	0.7750	77.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.21%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.10%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.53%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.36%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.91%	89.62%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.56%	94.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.40%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.74%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.10%	95.83%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.01%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.93%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.22%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.14%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.82%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.42%	89.00%
CHEMBL4208	P20618	Proteasome component C5	82.39%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.53%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	80.85%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	80.51%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.47%	96.77%

Plants that contains it

• Atractylodes lancea
• Chiloscyphus rivularis
• Conocarpus erectus
• Fabiana imbricata
• Lupinus pilosus
• Magnolia fraseri
• Mimosa pudica
• Physochlaina physaloides
• Rubus occidentalis
• Scopolia carniolica
• Scopolia japonica

Cross-Links

• PubChem: 10994544
• NPASS: NPC262047
• LOTUS: LTS0125933
• wikiData: Q104912159