Fischeroside B

Details

• Internal ID: 426dd49d-9fed-4235-b17e-1b69508f7a68
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(1R,2S,6R,10S,11R,13S,15R)-13-acetyloxy-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxo-8-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): CC1CC2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)COC5C(C(C(C(O5)COC(=O)C6=CC(=C(C(=C6)O)O)O)O)O)O)O)C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@]2([C@@H](C2(C)C)[C@H]3[C@]1([C@@H]4C=C(C(=O)[C@]4(CC(=C3)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C6=CC(=C(C(=C6)O)O)O)O)O)O)O)C)O)OC(=O)C
• InChI: InChI=1S/C35H44O15/c1-14-6-23-33(45,29(14)43)11-17(7-19-28-32(4,5)34(28,50-16(3)36)10-15(2)35(19,23)46)12-48-31-27(42)26(41)25(40)22(49-31)13-47-30(44)18-8-20(37)24(39)21(38)9-18/h6-9,15,19,22-23,25-28,31,37-42,45-46H,10-13H2,1-5H3/t15-,19+,22-,23-,25-,26+,27-,28-,31-,33-,34+,35-/m1/s1
• InChI Key: HILKKSGKHWLFAN-QWOHJRRRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₅
• Molecular Weight: 704.70 g/mol
• Exact Mass: 704.26802069 g/mol
• Topological Polar Surface Area (TPSA): 250.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.34
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• RefChem:921620
• ((2R,3S,4S,5R,6R)-6-(((1R,2S,6R,10S,11R,13S,15R)-13-acetyloxy-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxo-8-tetracyclo(8.5.0.02,6.011,13)pentadeca-3,8-dienyl)methoxy)-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate
• CHEBI:69816
• Fischerosides B
• CHEMBL1813582
• Q27138158
• (1aR,1bS,4aR,7aS,7bR,8R,9aS)-4a,7b-Dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-({[6-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl]oxy}methyl)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate
• [(2R,3S,4S,5R,6R)-6-[(acetoxy-dihydroxy-tetramethyl-oxo-[?]yl)methoxy]-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl 3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9149	91.49%
Caco-2	-	0.8738	87.38%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6034	60.34%
OATP2B1 inhibitior	-	0.7195	71.95%
OATP1B1 inhibitior	+	0.7823	78.23%
OATP1B3 inhibitior	+	0.9147	91.47%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7022	70.22%
P-glycoprotein inhibitior	+	0.7124	71.24%
P-glycoprotein substrate	+	0.5812	58.12%
CYP3A4 substrate	+	0.7215	72.15%
CYP2C9 substrate	-	0.8015	80.15%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.8772	87.72%
CYP2C9 inhibition	-	0.5312	53.12%
CYP2C19 inhibition	-	0.6108	61.08%
CYP2D6 inhibition	-	0.8676	86.76%
CYP1A2 inhibition	+	0.5431	54.31%
CYP2C8 inhibition	+	0.7515	75.15%
CYP inhibitory promiscuity	-	0.7617	76.17%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6537	65.37%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9111	91.11%
Skin irritation	-	0.7389	73.89%
Skin corrosion	-	0.9310	93.10%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5492	54.92%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.7280	72.80%
skin sensitisation	-	0.7859	78.59%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8156	81.56%
Acute Oral Toxicity (c)	III	0.4193	41.93%
Estrogen receptor binding	+	0.7797	77.97%
Androgen receptor binding	+	0.7480	74.80%
Thyroid receptor binding	+	0.5228	52.28%
Glucocorticoid receptor binding	+	0.7325	73.25%
Aromatase binding	+	0.7173	71.73%
PPAR gamma	+	0.7470	74.70%
Honey bee toxicity	-	0.7365	73.65%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9896	98.96%

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	99.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.07%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.88%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.74%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.96%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	90.89%	92.50%
CHEMBL4208	P20618	Proteasome component C5	89.93%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.47%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.19%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.76%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	88.53%	94.75%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.71%	83.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.83%	100.00%
CHEMBL4794	Q8NER1	Vanilloid receptor	86.27%	98.97%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.54%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.53%	94.42%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.25%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.43%	93.04%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.18%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	81.52%	94.45%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.31%	82.38%
CHEMBL2996	Q05655	Protein kinase C delta	80.99%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.54%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.49%	95.64%

Plants that contains it

• Euphorbia fischeriana

Cross-Links

• PubChem: 53360348
• NPASS: NPC102367
• ChEMBL: CHEMBL1813582
• LOTUS: LTS0004157
• wikiData: Q27138158