Clemastanin B

Details

• Internal ID: 6547f0d6-06c2-4da1-8fa8-c1bf06d6d9b8
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[[(3R,4R,5S)-4-(hydroxymethyl)-5-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]oxolan-3-yl]methyl]-2-methoxyphenoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@H]2CO[C@@H]([C@H]2CO)C3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C32H44O16/c1-42-20-8-14(3-5-18(20)45-31-28(40)26(38)24(36)22(11-34)47-31)7-16-13-44-30(17(16)10-33)15-4-6-19(21(9-15)43-2)46-32-29(41)27(39)25(37)23(12-35)48-32/h3-6,8-9,16-17,22-41H,7,10-13H2,1-2H3/t16-,17-,22+,23+,24+,25+,26-,27-,28+,29+,30+,31+,32+/m0/s1
• InChI Key: PBLWZMSRSJTRHJ-NCIRKIHRSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₄O₁₆
• Molecular Weight: 684.70 g/mol
• Exact Mass: 684.26293531 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.40
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

• 112747-98-5
• (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[4-[[(3R,4R,5S)-4-(hydroxymethyl)-5-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]oxolan-3-yl]methyl]-2-methoxyphenoxy]oxane-3,4,5-triol
• HY-N6025
• AKOS040760335
• MS-31107
• CS-0032192
• LAriciresinol 4,4'-bis-O-|A-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7025	70.25%
Caco-2	-	0.8633	86.33%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8022	80.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8574	85.74%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7690	76.90%
P-glycoprotein inhibitior	+	0.6466	64.66%
P-glycoprotein substrate	-	0.7098	70.98%
CYP3A4 substrate	+	0.6310	63.10%
CYP2C9 substrate	-	0.8048	80.48%
CYP2D6 substrate	-	0.7822	78.22%
CYP3A4 inhibition	-	0.7667	76.67%
CYP2C9 inhibition	-	0.8245	82.45%
CYP2C19 inhibition	-	0.7386	73.86%
CYP2D6 inhibition	-	0.8963	89.63%
CYP1A2 inhibition	-	0.8578	85.78%
CYP2C8 inhibition	+	0.6944	69.44%
CYP inhibitory promiscuity	+	0.5593	55.93%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6301	63.01%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9128	91.28%
Skin irritation	-	0.8573	85.73%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8745	87.45%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8831	88.31%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9212	92.12%
Acute Oral Toxicity (c)	III	0.7137	71.37%
Estrogen receptor binding	+	0.7732	77.32%
Androgen receptor binding	+	0.5612	56.12%
Thyroid receptor binding	+	0.5287	52.87%
Glucocorticoid receptor binding	+	0.5703	57.03%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6861	68.61%
Honey bee toxicity	-	0.7884	78.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.8946	89.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.78%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.02%	98.95%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	91.86%	85.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.59%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.59%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.90%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.74%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.13%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.12%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.13%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.90%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.83%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.11%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.97%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.33%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.02%	92.94%
CHEMBL4208	P20618	Proteasome component C5	82.80%	90.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.48%	89.44%
CHEMBL3401	O75469	Pregnane X receptor	81.11%	94.73%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.34%	97.33%

Plants that contains it

• Clematis stans
• Galium sinaicum
• Isatis tinctoria
• Plocama calabrica
• Sedum sarmentosum

Cross-Links

• PubChem: 10009802
• NPASS: NPC307007
• LOTUS: LTS0003636
• wikiData: Q105205263