Plantaginin

Details

• Internal ID: db64a893-ce2d-4d2f-85b5-b17142ffba4d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-14-17(26)19(28)20(29)21(32-14)31-13-6-12-15(18(27)16(13)25)10(24)5-11(30-12)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21-/m1/s1
• InChI Key: VUGRLRAUZWGZJP-IAAKTDFRSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• CHEBI:80895
• Scutellarein 7beta-D-glucopyranoside
• 26046-94-6
• 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• Scutellarein-7-O-glucoside
• SCHEMBL6238317
• CHEMBL2312739
• DTXSID601318276
• AKOS040762320
• C17056
• Q27151393
• 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9378	93.78%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.6067	60.67%
OATP1B1 inhibitior	+	0.8362	83.62%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5692	56.92%
P-glycoprotein inhibitior	-	0.7975	79.75%
P-glycoprotein substrate	-	0.8087	80.87%
CYP3A4 substrate	+	0.5853	58.53%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
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	+	0.7730	77.30%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8422	84.22%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4914	49.14%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8571	85.71%
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	-	0.8666	86.66%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7179	71.79%
Androgen receptor binding	+	0.7832	78.32%
Thyroid receptor binding	+	0.5546	55.46%
Glucocorticoid receptor binding	+	0.6656	66.56%
Aromatase binding	+	0.6511	65.11%
PPAR gamma	+	0.7805	78.05%
Honey bee toxicity	-	0.6402	64.02%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6049	60.49%
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	98.93%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.24%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.48%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.71%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.19%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.52%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.99%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.88%	95.78%
CHEMBL3194	P02766	Transthyretin	89.55%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.46%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	89.22%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.08%	95.89%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.07%	83.57%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.60%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.49%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.87%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.58%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.85%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.52%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.66%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.18%	99.15%

Plants that contains it

• Allium stipitatum
• Alstonia longifolia
• Anaphalis sinica
• Angiopteris evecta
• Artemisia argentea
• Asphodeline damascena
• Brodiaea californica
• Buddleja madagascariensis
• Crocus chrysanthus
• Cyathula tomentosa
• Echinostephia aculeata
• Eucalyptus kitsoniana
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Halophila ovalis subsp. ovalis
• Helichrysum arenarium
• Hemionitis lemmonii
• Himantoglossum hircinum
• Kopsia arborea
• Lantana trifolia
• Lepidophorum repandum
• Myristica malabarica
• Odontites vernus
• Origanum majorana
• Persicaria hydropiper
• Plagiomnium cuspidatum
• Plantago asiatica
• Plantago depressa
• Plantago major
• Plectranthus lanuginosus
• Populus yunnanensis
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Sagina japonica
• Scabiosa comosa
• Scapania aequiloba
• Scutellaria indica
• Scutellaria phyllostachya
• Scutellaria schachristanica
• Solanum dulcamara
• Spartium junceum
• Stachys officinalis
• Toddalia asiatica
• Vachellia lasiopetala
• Zanthoxylum armatum

Cross-Links

• PubChem: 5320623
• NPASS: NPC146792
• ChEMBL: CHEMBL2312739
• LOTUS: LTS0093185
• wikiData: Q27151393