Frangulin B

Details

• Internal ID: 572aefb1-b616-4191-a729-293a38b03a33
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-1,8-dihydroxy-6-methylanthracene-9,10-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)OC4C(C(CO4)(CO)O)O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O[C@H]4[C@@H]([C@](CO4)(CO)O)O
• InChI: InChI=1S/C20H18O9/c1-8-2-10-14(12(22)3-8)17(25)15-11(16(10)24)4-9(5-13(15)23)29-19-18(26)20(27,6-21)7-28-19/h2-5,18-19,21-23,26-27H,6-7H2,1H3/t18-,19-,20+/m0/s1
• InChI Key: AEQMIFRODRFTJF-SLFFLAALSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₉
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.09508215 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.00
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 14101-04-3
• CHEMBL496999
• UNII-8CIK094KBU
• 8CIK094KBU
• CHEBI:5168
• C10349
• EINECS 237-953-9
• 3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-1,8-dihydroxy-6-methylanthracene-9,10-dione
• 6-O-(D-Apiofuranosyl)-1,6,8-trihydroxy-3-methylanthraquinone
• 3-(D-Apio-beta-D-furanosyloxy)-1,8-dihydroxy-6-methylanthraquinone
• AC1L9DBZ
• FRANGULINB
• FRANGULIN B [MI]
• SureCN1426453
• SCHEMBL1426453
• Frangulin B, analytical standard
• DTXSID80930972
• CHEBI:601858
• BDBM50269014
• MFCD00016362
• AKOS015914181
• A807715
• Q27106674
• 9,10-Anthracenedione,3-(D-apio-b-D-furanosyloxy)-1,8-dihydroxy-6-methyl-
• 9,10-ANTHRACENEDIONE, 3-(D-APIO-.BETA.-D-FURANOSYLOXY)-1,8-DIHYDROXY-6-METHYL-
• 3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-1,8-dihydroxy-6-methyl-anthracene-9,10-dione
• 3-[(2S,3R,4R)-4-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]oxy-6-methyl-1,8-bis(oxidanyl)anthracene-9,10-dione
• 3-[[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)-2-oxolanyl]oxy]-1,8-dihydroxy-6-methylanthracene-9,10-dione
• 3-{[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1,8-dihydroxy-6-methylanthracene-9,10-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7752	77.52%
Caco-2	-	0.7924	79.24%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5902	59.02%
OATP2B1 inhibitior	-	0.5679	56.79%
OATP1B1 inhibitior	+	0.9376	93.76%
OATP1B3 inhibitior	+	0.9607	96.07%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6723	67.23%
P-glycoprotein substrate	-	0.8546	85.46%
CYP3A4 substrate	+	0.6208	62.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8643	86.43%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8481	84.81%
CYP2C19 inhibition	-	0.8390	83.90%
CYP2D6 inhibition	-	0.9478	94.78%
CYP1A2 inhibition	-	0.7906	79.06%
CYP2C8 inhibition	-	0.6426	64.26%
CYP inhibitory promiscuity	-	0.7921	79.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5444	54.44%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.7908	79.08%
Skin irritation	-	0.8142	81.42%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5658	56.58%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	+	0.5302	53.02%
skin sensitisation	-	0.8536	85.36%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7537	75.37%
Acute Oral Toxicity (c)	III	0.6086	60.86%
Estrogen receptor binding	+	0.8834	88.34%
Androgen receptor binding	+	0.6358	63.58%
Thyroid receptor binding	-	0.5076	50.76%
Glucocorticoid receptor binding	+	0.7511	75.11%
Aromatase binding	+	0.7412	74.12%
PPAR gamma	+	0.7163	71.63%
Honey bee toxicity	-	0.8293	82.93%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.9090	90.90%

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	98.76%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.65%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.99%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.78%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.31%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.94%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	93.70%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.16%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.53%	99.15%
CHEMBL4208	P20618	Proteasome component C5	91.91%	90.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.95%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.45%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.06%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.80%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.90%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.85%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.18%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	84.16%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.09%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	83.04%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.95%	96.21%
CHEMBL4581	P52732	Kinesin-like protein 1	81.25%	93.18%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.52%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.31%	100.00%

Plants that contains it

• Frangula alnus
• Rhamnus cathartica
• Rhamnus formosana

Cross-Links

• PubChem: 442744
• NPASS: NPC98776
• ChEMBL: CHEMBL496999
• LOTUS: LTS0176006
• wikiData: Q27106674