Sagittatoside B

Details

• Internal ID: 7f12d38f-d886-42a7-9f71-a3c849b69c97
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)OC)OC5C(C(C(CO5)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)OC)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O
• InChI: InChI=1S/C32H38O14/c1-13(2)5-10-17-18(33)11-19(34)21-24(38)29(27(44-28(17)21)15-6-8-16(41-4)9-7-15)45-32-30(25(39)22(36)14(3)43-32)46-31-26(40)23(37)20(35)12-42-31/h5-9,11,14,20,22-23,25-26,30-37,39-40H,10,12H2,1-4H3/t14-,20+,22-,23-,25+,26+,30+,31-,32-/m0/s1
• InChI Key: BVDGQVAUJNUPGW-JGSSSOFVSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₄
• Molecular Weight: 646.60 g/mol
• Exact Mass: 646.22615588 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.06
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 118525-36-3
• Sagittatosdie B
• 3-[(2S,3R,4R,5R,6S)-4,5-Dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• CHEBI:187243
• HY-N0874
• MFCD28411516
• CS-3691
• MS-30943
• 3-(((2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• 3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9012	90.12%
Caco-2	-	0.9208	92.08%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6224	62.24%
OATP2B1 inhibitior	-	0.7159	71.59%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9319	93.19%
P-glycoprotein inhibitior	+	0.5747	57.47%
P-glycoprotein substrate	+	0.6243	62.43%
CYP3A4 substrate	+	0.6814	68.14%
CYP2C9 substrate	-	0.6946	69.46%
CYP2D6 substrate	-	0.8431	84.31%
CYP3A4 inhibition	-	0.9197	91.97%
CYP2C9 inhibition	-	0.7778	77.78%
CYP2C19 inhibition	-	0.6913	69.13%
CYP2D6 inhibition	-	0.7351	73.51%
CYP1A2 inhibition	-	0.6879	68.79%
CYP2C8 inhibition	+	0.6543	65.43%
CYP inhibitory promiscuity	-	0.6733	67.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7134	71.34%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9194	91.94%
Skin irritation	-	0.7907	79.07%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	-	0.5274	52.74%
Human Ether-a-go-go-Related Gene inhibition	+	0.7176	71.76%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.8642	86.42%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9502	95.02%
Acute Oral Toxicity (c)	III	0.6247	62.47%
Estrogen receptor binding	+	0.8562	85.62%
Androgen receptor binding	+	0.7091	70.91%
Thyroid receptor binding	+	0.5925	59.25%
Glucocorticoid receptor binding	+	0.7395	73.95%
Aromatase binding	+	0.6170	61.70%
PPAR gamma	+	0.7142	71.42%
Honey bee toxicity	-	0.7241	72.41%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9734	97.34%

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	99.92%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.27%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.97%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.91%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.70%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.77%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.24%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.06%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.94%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.22%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.14%	94.45%
CHEMBL4208	P20618	Proteasome component C5	90.22%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.61%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.58%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.22%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.89%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.00%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.92%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.76%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.32%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.06%	92.62%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.62%	97.53%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.26%	96.77%

Plants that contains it

• Epimedium brevicornu
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense

Cross-Links

• PubChem: 10146160
• NPASS: NPC67142