Narirutin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	684d91ec-5c30-48d5-b706-79d7638f083d
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name	(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
SMILES (Canonical)	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
SMILES (Isomeric)	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
InChI	InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
InChI Key	HXTFHSYLYXVTHC-AJHDJQPGSA-N
Popularity	500 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₇H₃₂O₁₄
Molecular Weight	580.50 g/mol
Exact Mass	580.17920569 g/mol
Topological Polar Surface Area (TPSA)	225.00 Å²
XlogP	-1.10
Atomic LogP (AlogP)	-1.17
H-Bond Acceptor	14
H-Bond Donor	8
Rotatable Bonds	6

Synonyms

Top

14259-46-2

Isonaringenin

Isonaringin

Naringenin 7-O-rutinoside

CHEBI:28705

06M5EAT0YC

DTXSID30931535

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-one

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5564	55.64%
Caco-2	-	0.9015	90.15%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7477	74.77%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.9326	93.26%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7419	74.19%
P-glycoprotein inhibitior	-	0.8285	82.85%
P-glycoprotein substrate	-	0.6664	66.64%
CYP3A4 substrate	+	0.6236	62.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.8673	86.73%
CYP2C8 inhibition	+	0.5093	50.93%
CYP inhibitory promiscuity	-	0.6787	67.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9173	91.73%
Skin irritation	-	0.8089	80.89%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6683	66.83%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.8833	88.33%
skin sensitisation	-	0.9325	93.25%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6724	67.24%
Acute Oral Toxicity (c)	III	0.5971	59.71%
Estrogen receptor binding	+	0.7737	77.37%
Androgen receptor binding	-	0.6637	66.37%
Thyroid receptor binding	+	0.5304	53.04%
Glucocorticoid receptor binding	+	0.5411	54.11%
Aromatase binding	+	0.5180	51.80%
PPAR gamma	+	0.7459	74.59%
Honey bee toxicity	-	0.7580	75.80%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.8993	89.93%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	99.49%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.57%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.32%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.45%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.32%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.97%	94.73%
CHEMBL4208	P20618	Proteasome component C5	90.95%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.38%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.12%	94.80%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.74%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.66%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.43%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.90%	97.36%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.04%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.76%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.60%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.72%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.53%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.44%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.68%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	80.59%	95.93%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.16%	85.00%

Plants that contains it

Top

Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Asterolasia squamuligera

Catharanthus roseus

Cinnamomum chekiangense

Citrus × aurantium

Citrus × aurantium nothof. deliciosa

Colchicum soboliferum

Cyclopia subternata

Foeniculum vulgare