Plantagoside

Details

• Internal ID: 1fc9d255-25c1-4ab5-9551-7806e2216fd2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2S)-2-[3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C(=C3)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C(=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H22O12/c22-6-15-18(28)19(29)20(30)21(33-15)32-14-2-7(1-11(26)17(14)27)12-5-10(25)16-9(24)3-8(23)4-13(16)31-12/h1-4,12,15,18-24,26-30H,5-6H2/t12-,15+,18+,19-,20+,21+/m0/s1
• InChI Key: SNFFBROYEDWRGB-NHXQFOETSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₂
• Molecular Weight: 466.40 g/mol
• Exact Mass: 466.11112613 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.61
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• 78708-33-5
• UNII-FR4TR9587N
• FR4TR9587N
• 2'-O-beta-Glucopyranosyl-5,7,4',5'-tetrahydroxyflavanone
• 4H-1-Benzopyran-4-one, 2-(3-(beta-D-glucopyranosyloxy)-4,5-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (S)-
• (2S)-2-[3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• CHEBI:81163
• DTXSID20229256
• HY-N1470
• s3254
• AKOS040760042
• AC-34116
• MS-28591
• CS-0016963
• C17531
• E87192
• 5,7,4',5'-tetrahydroxyflavanone-3'-O-glucoside
• Q-100956
• Q27155118
• (S)-2-(3,4-Dihydroxy-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-5,7-dihydroxychroman-4-one
• 4H-1-BENZOPYRAN-4-ONE, 2-(3-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,5-DIHYDROXYPHENYL)-2,3-DIHYDRO-5,7-DIHYDROXY-, (2S)-
• 4H-1-BENZOPYRAN-4-ONE, 2-(3-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,5-DIHYDROXYPHENYL)-2,3-DIHYDRO-5,7-DIHYDROXY-, (S)-
• 5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2,3-dihydroxyphenyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9346	93.46%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5744	57.44%
OATP1B1 inhibitior	+	0.9201	92.01%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6058	60.58%
P-glycoprotein inhibitior	-	0.7387	73.87%
P-glycoprotein substrate	-	0.8677	86.77%
CYP3A4 substrate	+	0.5893	58.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8398	83.98%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.4791	47.91%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8353	83.53%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4738	47.38%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5879	58.79%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7749	77.49%
Androgen receptor binding	-	0.5142	51.42%
Thyroid receptor binding	+	0.5895	58.95%
Glucocorticoid receptor binding	+	0.5561	55.61%
Aromatase binding	-	0.5193	51.93%
PPAR gamma	+	0.7066	70.66%
Honey bee toxicity	-	0.7141	71.41%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.45%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.33%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.02%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.31%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.44%	94.00%
CHEMBL2581	P07339	Cathepsin D	90.40%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.35%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.10%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.62%	85.14%
CHEMBL4208	P20618	Proteasome component C5	88.34%	90.00%
CHEMBL3194	P02766	Transthyretin	88.29%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.95%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.71%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.35%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.30%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.01%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.41%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	83.04%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.34%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.08%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.12%	95.78%

Plants that contains it

• Allium stipitatum
• Alstonia longifolia
• Angiopteris evecta
• Artemisia argentea
• Asphodeline damascena
• Brodiaea californica
• Cyathula tomentosa
• Echinostephia aculeata
• Eucalyptus kitsoniana
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Hemionitis lemmonii
• Himantoglossum hircinum
• Kopsia arborea
• Lepidophorum repandum
• Myristica malabarica
• Odontites vernus
• Plagiomnium cuspidatum
• Plantago asiatica
• Plantago depressa
• Plantago major
• Plectranthus lanuginosus
• Populus yunnanensis
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Sagina japonica
• Scabiosa comosa
• Scapania aequiloba
• Solanum dulcamara
• Spartium junceum
• Toddalia asiatica
• Vachellia lasiopetala

Cross-Links

• PubChem: 174157
• NPASS: NPC72615
• LOTUS: LTS0036853
• wikiData: Q27155118