Sphaerobioside

Details

• Internal ID: 17609035-3e23-4fa7-87c8-104c36eb8bdc
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC=C(C4=O)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=C3)OC=C(C4=O)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O14/c1-10-19(30)22(33)24(35)26(39-10)38-9-17-21(32)23(34)25(36)27(41-17)40-13-6-15(29)18-16(7-13)37-8-14(20(18)31)11-2-4-12(28)5-3-11/h2-8,10,17,19,21-30,32-36H,9H2,1H3/t10-,17+,19-,21+,22+,23-,24+,25+,26+,27+/m0/s1
• InChI Key: XIQCIPHUIZGDLB-SEPMLUPWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• Sphaerobioside
• 14988-20-6
• 5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CHEMBL2227762
• XS161546

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5564	55.64%
Caco-2	-	0.8961	89.61%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7477	74.77%
OATP2B1 inhibitior	-	0.7017	70.17%
OATP1B1 inhibitior	+	0.9323	93.23%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7229	72.29%
P-glycoprotein inhibitior	-	0.7156	71.56%
P-glycoprotein substrate	-	0.6450	64.50%
CYP3A4 substrate	+	0.6229	62.29%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.8673	86.73%
CYP2C8 inhibition	+	0.6839	68.39%
CYP inhibitory promiscuity	-	0.6787	67.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9166	91.66%
Skin irritation	-	0.8089	80.89%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6697	66.97%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9325	93.25%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7176	71.76%
Acute Oral Toxicity (c)	III	0.5971	59.71%
Estrogen receptor binding	+	0.7257	72.57%
Androgen receptor binding	+	0.5487	54.87%
Thyroid receptor binding	-	0.4881	48.81%
Glucocorticoid receptor binding	+	0.5760	57.60%
Aromatase binding	+	0.5615	56.15%
PPAR gamma	+	0.7549	75.49%
Honey bee toxicity	-	0.7846	78.46%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.8993	89.93%

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	99.04%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.55%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.40%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.12%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.92%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.36%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.73%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.64%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.14%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	89.76%	98.35%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.99%	91.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.79%	95.64%
CHEMBL226	P30542	Adenosine A1 receptor	87.39%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	87.30%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.18%	95.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.17%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.08%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.78%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.37%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.23%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.38%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.30%	96.21%
CHEMBL3194	P02766	Transthyretin	81.01%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.88%	95.83%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.65%	90.71%
CHEMBL4208	P20618	Proteasome component C5	80.24%	90.00%

Plants that contains it

• Brachypterum scandens
• Deguelia scandens
• Eriosema tuberosum
• Picradeniopsis multiflora

Cross-Links

• PubChem: 76315025
• NPASS: NPC303913
• LOTUS: LTS0212670
• wikiData: Q105152086