Cleistanthin B

Details

• Internal ID: 5bdd7329-94d5-414e-a724-be4a266f8c86
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3C(=C2OC4C(C(C(C(O4)CO)O)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3C(=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• InChI: InChI=1S/C27H26O12/c1-33-16-6-12-13(7-17(16)34-2)25(39-27-24(31)23(30)22(29)19(8-28)38-27)14-9-35-26(32)21(14)20(12)11-3-4-15-18(5-11)37-10-36-15/h3-7,19,22-24,27-31H,8-10H2,1-2H3/t19-,22-,23+,24-,27+/m1/s1
• InChI Key: BJGIWVGXMRUMNA-WBYCZGBQSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₁₂
• Molecular Weight: 542.50 g/mol
• Exact Mass: 542.14242626 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• 30021-77-3
• Clei B
• Diphyllin O-glucoside
• GNF-Pf-349
• CHEBI:84407
• 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one
• 9-(1,3-Benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxynaphtho(2,3-c)furan-1(3H)-one
• 9-(1,3-benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one
• diphyllin beta-D-glucoside
• CHEMBL601587
• DTXSID501014455
• HY-N9351
• C27H26O12
• 4-O-(beta-D-glucopyranosyl)diphyllin
• AKOS040735117
• MS-29983
• CS-0159499
• Q27157736
• 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-1,3-dihydronaphtho[2,3-c]furan-4-yl beta-D-glucopyranoside
• Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5958	59.58%
Caco-2	-	0.7965	79.65%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6367	63.67%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.9014	90.14%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9146	91.46%
P-glycoprotein inhibitior	-	0.4446	44.46%
P-glycoprotein substrate	-	0.7316	73.16%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8522	85.22%
CYP3A4 inhibition	-	0.5237	52.37%
CYP2C9 inhibition	-	0.8011	80.11%
CYP2C19 inhibition	-	0.7261	72.61%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.9203	92.03%
CYP2C8 inhibition	+	0.5683	56.83%
CYP inhibitory promiscuity	+	0.6363	63.63%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6053	60.53%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9320	93.20%
Skin irritation	-	0.8240	82.40%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	+	0.6163	61.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6762	67.62%
Micronuclear	+	0.7133	71.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8827	88.27%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6410	64.10%
Acute Oral Toxicity (c)	III	0.7719	77.19%
Estrogen receptor binding	+	0.7702	77.02%
Androgen receptor binding	+	0.6182	61.82%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6674	66.74%
Aromatase binding	-	0.5884	58.84%
PPAR gamma	+	0.6022	60.22%
Honey bee toxicity	-	0.7364	73.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6149	61.49%
Fish aquatic toxicity	+	0.7675	76.75%

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	99.14%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.07%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.78%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.58%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.53%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.17%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.73%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.63%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.90%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.74%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.67%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.53%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.40%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.59%	96.00%
CHEMBL2535	P11166	Glucose transporter	87.44%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.25%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.87%	100.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.61%	92.38%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.58%	96.21%
CHEMBL1951	P21397	Monoamine oxidase A	82.74%	91.49%
CHEMBL1907	P15144	Aminopeptidase N	81.05%	93.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.96%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	80.32%	94.73%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.30%	97.50%
CHEMBL4208	P20618	Proteasome component C5	80.21%	90.00%

Plants that contains it

• Cleistanthus collinus
• Haplophyllum cappadocicum
• Hypoestes purpurea
• Podophyllum versipelle

Cross-Links

• PubChem: 119458
• NPASS: NPC129930
• ChEMBL: CHEMBL601587
• LOTUS: LTS0029478
• wikiData: Q27157736