Nepitrin

Details

• Internal ID: 547be25c-bdef-4b05-bc79-8e05b1002c73
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC(=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC(=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C22H22O12/c1-31-21-14(33-22-20(30)19(29)17(27)15(7-23)34-22)6-13-16(18(21)28)11(26)5-12(32-13)8-2-3-9(24)10(25)4-8/h2-6,15,17,19-20,22-25,27-30H,7H2,1H3/t15-,17-,19+,20-,22-/m1/s1
• InChI Key: DMXHXBGUNHLMQO-IWLDQSELSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₂
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.11112613 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• Nepetin-7-glucoside
• 569-90-4
• Nepetin 7-glucoside
• Eupatolin 7-glucoside
• 6-Methoxyluteolin 7-glucoside
• 3',4',5-Trihydroxy-6-methoxy-7-(glucosyloxy)flavone
• UNII-S9ZMJ20NUO
• S9ZMJ20NUO
• 5,3,4-Trihydroxy-6-methoxyflavonoid
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-6-methoxy-
• 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-6-METHOXY-7-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY)-4H-CHROMEN-4-ONE
• 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• NEPETRIN
• Eupafolin-7-glucoside
• Nepetin-7-glucopyranoside
• 6-Methoxyluteolin-7-glucoside
• NEPETIN 7-O-GLUCOSIDE
• CHEMBL517682
• DTXSID00972339
• CHEBI:191783
• HY-N5010
• MFCD01662760
• EUPAFOLIN 7-.BETA.-GLUCOSIDE
• AKOS037514751
• 6-METHOXYLUTEOLIN 7-O-GLUCOSIDE
• EUPAFOLIN 7-O-.BETA.-GLUCOSIDE
• NEPETIN 7-O-.BETA.-D-GLUCOSIDE
• AC-34360
• J16.151I
• LS-39607
• MS-28870
• CS-0032071
• NEPETIN 7-O-.BETA.-D-GLUCOPYRANOSIDE
• EUPAFOLIN 7-O-.BETA.-D-GLUCOPYRANOSIDE
• Q-100656
• Q27289103
• 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-1-benzopyran-7-yl hexopyranoside
• FLAVONE, 3',4',5,7-TETRAHYDROXY-6-METHOXY-, 7-.BETA.-D-GLUCOPYRANOSIDE
• 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-6-METHOXY-4-OXO-4H-CHROMEN-7-YL .BETA.-D-GLUCOPYRANOSIDE
• 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-6-METHOXY-7-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY)CHROMEN-4-ONE
• 4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-6-METHOXY-
• 5-HYDROXY-6-METHOXY-2-(3,4-DIHYDROXYPHENYL)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-4H-1-BENZOPYRAN-4-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8982	89.82%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5411	54.11%
OATP1B1 inhibitior	+	0.8386	83.86%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7289	72.89%
P-glycoprotein inhibitior	-	0.6936	69.36%
P-glycoprotein substrate	-	0.6297	62.97%
CYP3A4 substrate	+	0.5944	59.44%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.7159	71.59%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9132	91.32%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.5236	52.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4352	43.52%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9267	92.67%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7779	77.79%
Androgen receptor binding	+	0.6638	66.38%
Thyroid receptor binding	+	0.5956	59.56%
Glucocorticoid receptor binding	+	0.7043	70.43%
Aromatase binding	-	0.4915	49.15%
PPAR gamma	+	0.7318	73.18%
Honey bee toxicity	-	0.7339	73.39%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7049	70.49%
Fish aquatic toxicity	+	0.7079	70.79%

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	99.76%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.97%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.10%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.14%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.92%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.68%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.99%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.38%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.30%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.04%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	86.83%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.31%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	85.94%	91.49%
CHEMBL3194	P02766	Transthyretin	85.61%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.41%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.98%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.28%	95.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.64%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.60%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.07%	97.09%

Plants that contains it

• Arnica chamissonis
• Arnica longifolia
• Eupatorium cannabinum
• Rosmarinus officinalis
• Salvia fruticosa
• Scrophularia ningpoensis
• Veronica thymoides

Cross-Links

• PubChem: 120742
• NPASS: NPC201292
• LOTUS: LTS0032877
• wikiData: Q27289103