Centaurein

Details

• Internal ID: 91e700b5-0876-4c77-b02b-53460732d425
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)OC)O)OC)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)O)OC)O
• InChI: InChI=1S/C24H26O13/c1-32-11-5-4-9(6-10(11)26)21-23(34-3)18(29)15-12(35-21)7-13(22(33-2)17(15)28)36-24-20(31)19(30)16(27)14(8-25)37-24/h4-7,14,16,19-20,24-28,30-31H,8H2,1-3H3/t14-,16-,19+,20-,24-/m1/s1
• InChI Key: GGMCFLXPZMBJMV-NPVWYNPDSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆O₁₃
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.13734088 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 35595-03-0
• UNII-Y985P9U3S7
• Y985P9U3S7
• 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-
• CENTAUREIN [MI]
• CENTAUREIN, (-)-
• CHEMBL484037
• DTXSID20189063
• Q27294400
• 3',5,7-trihydroxy-3,4',6-trimethoxyflavone 7-beta-D-glucoside
• 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-
• 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-3,6-DIMETHOXY-4H-1-BENZOPYRAN-4-ONE
• NCGC00385512-01!5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5088	50.88%
Caco-2	-	0.8585	85.85%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6030	60.30%
OATP2B1 inhibitior	-	0.7028	70.28%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7562	75.62%
P-glycoprotein inhibitior	-	0.5120	51.20%
P-glycoprotein substrate	-	0.5644	56.44%
CYP3A4 substrate	+	0.6115	61.15%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9371	93.71%
CYP2C9 inhibition	-	0.9410	94.10%
CYP2C19 inhibition	-	0.9438	94.38%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.9134	91.34%
CYP2C8 inhibition	+	0.8078	80.78%
CYP inhibitory promiscuity	-	0.7474	74.74%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7050	70.50%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9181	91.81%
Skin irritation	-	0.8406	84.06%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.5064	50.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.6626	66.26%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9409	94.09%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9139	91.39%
Acute Oral Toxicity (c)	III	0.6685	66.85%
Estrogen receptor binding	+	0.8515	85.15%
Androgen receptor binding	+	0.5921	59.21%
Thyroid receptor binding	+	0.5670	56.70%
Glucocorticoid receptor binding	+	0.7142	71.42%
Aromatase binding	+	0.5689	56.89%
PPAR gamma	+	0.6884	68.84%
Honey bee toxicity	-	0.7925	79.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6949	69.49%
Fish aquatic toxicity	+	0.7605	76.05%

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	98.85%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.36%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.73%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.52%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.12%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.29%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.53%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.86%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.34%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.02%	95.64%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.57%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.48%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.46%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	84.95%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.97%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.11%	96.21%

Plants that contains it

• Achillea nana
• Aconitum napellus
• Astragalus bisulcatus
• Baccharoides lasiopus
• Bidens pilosa
• Boenninghausenia albiflora
• Bothriocline ripensis
• Brachyglottis bidwillii
• Brickellia glutinosa
• Calea lantanoides
• Centaurea corcubionensis
• Centaurea nigra
• Chromolaena odorata
• Cibotium barometz
• Coronilla cretica
• Drosera indica
• Drummondita hassellii
• Ephedra distachya
• Flindersia xanthoxyla
• Galinsoga quadriradiata
• Galium mollugo
• Gardenia imperialis
• Gomesa radicans
• Grindelia scorzonerifolia
• Lepidium graminifolium
• Lonchocarpus atropurpureus
• Pinus flexilis
• Psilotum nudum
• Ranunculus laetus
• Rydingia limbata
• Senegalia mellifera
• Tridax procumbens
• Typha latifolia
• Uncaria sterrophylla
• Vicia amoena

Cross-Links

• PubChem: 5489090
• NPASS: NPC21666
• LOTUS: LTS0088902
• wikiData: Q27294400