Gelomuloside B

Details

• Internal ID: 2e688f19-d183-4693-adc3-ec93937bfd75
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(CO5)O)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O
• InChI: InChI=1S/C28H32O15/c1-37-12-5-3-11(4-6-12)15-7-13(30)19-16(40-15)8-17(38-2)25(22(19)34)42-28-26(23(35)21(33)18(9-29)41-28)43-27-24(36)20(32)14(31)10-39-27/h3-8,14,18,20-21,23-24,26-29,31-36H,9-10H2,1-2H3/t14-,18-,20+,21-,23+,24-,26-,27+,28+/m1/s1
• InChI Key: FLNGHKQBVLFAGJ-IIYXSDHHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.18
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 149998-39-0
• 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
• GelomulosideB
• DTXSID901107959
• AKOS032962642
• 6-[(2-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-4',7-dimethoxyflavone
• 5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-6-[(2-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8859	88.59%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5131	51.31%
OATP2B1 inhibitior	-	0.8473	84.73%
OATP1B1 inhibitior	+	0.8043	80.43%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6669	66.69%
P-glycoprotein inhibitior	-	0.5780	57.80%
P-glycoprotein substrate	+	0.5177	51.77%
CYP3A4 substrate	+	0.6842	68.42%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9256	92.56%
CYP2C9 inhibition	-	0.9546	95.46%
CYP2C19 inhibition	-	0.9465	94.65%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.9248	92.48%
CYP2C8 inhibition	+	0.6693	66.93%
CYP inhibitory promiscuity	-	0.8563	85.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7040	70.40%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9337	93.37%
Skin irritation	-	0.8352	83.52%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	+	0.5736	57.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6494	64.94%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9283	92.83%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9795	97.95%
Acute Oral Toxicity (c)	III	0.7477	74.77%
Estrogen receptor binding	+	0.8473	84.73%
Androgen receptor binding	+	0.7101	71.01%
Thyroid receptor binding	+	0.5496	54.96%
Glucocorticoid receptor binding	+	0.7058	70.58%
Aromatase binding	+	0.6112	61.12%
PPAR gamma	+	0.7595	75.95%
Honey bee toxicity	-	0.7228	72.28%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.3639	36.39%

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	99.79%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.33%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	98.27%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.27%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.24%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.94%	86.92%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.73%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.28%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.90%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.31%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.11%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	89.77%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.53%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.52%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.07%	99.17%
CHEMBL4208	P20618	Proteasome component C5	87.18%	90.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.64%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.48%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.34%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.51%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.71%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.52%	95.89%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.98%	89.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.71%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	80.63%	94.73%

Plants that contains it

• Strychnos nux-vomica
• Suregada multiflora

Cross-Links

• PubChem: 102147924
• NPASS: NPC14897
• LOTUS: LTS0092410
• wikiData: Q104997273