Poncirin

Details

• Internal ID: 2b9bf888-0ec8-4cf6-9e9c-f9ff5dd89a7b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)OC)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)OC)O)CO)O)O)O)O)O
• InChI: InChI=1S/C28H34O14/c1-11-21(32)23(34)25(36)27(38-11)42-26-24(35)22(33)19(10-29)41-28(26)39-14-7-15(30)20-16(31)9-17(40-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-30,32-36H,9-10H2,1-2H3/t11-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChI Key: NLAWPKPYBMEWIR-SKYQDXIQSA-N
• Popularity: 33 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₄
• Molecular Weight: 594.60 g/mol
• Exact Mass: 594.19485575 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.86
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 14941-08-3
• Isosakuranetin-7-O-neohesperidoside
• Citrifolioside
• CHEBI:66773
• UNII-8MUY4P95B4
• 8MUY4P95B4
• Isosakuranetin 7-O-neohesperidoside
• (2S)-poncirin
• EINECS 239-020-1
• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• (S)-7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4H-benzopyran-4-one
• C28H34O14
• C28-H34-O14
• (S)-7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4H-benzopyran-4-one
• Isosakuranetin-7-O-beta-D-neohesperidoside
• SureCN123069
• Poncirin, analytical standard
• SCHEMBL123069
• CHEMBL451050
• DTXSID00933642
• NLAWPKPYBMEWIR-SKYQDXIQSA-N
• 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (S)-
• HY-N2258
• s9165
• AKOS037514792
• CCG-270181
• NCGC00163611-01
• AC-34235
• CS-0019587
• C09830
• Q3388129
• (2S)-5-hydroxy-2-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chroman-4-one
• (2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• (S)-7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-BENZOPYRAN-4-ONE
• 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (2S)-
• 5,7-Dihydroxy-4'-methoxyflavanone, 7-(2-O-.alpha.-L-rhamnopyranosyl-.beta.-D-glucopyranoside)
• 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8768	87.68%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.9857	98.57%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9360	93.60%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6718	67.18%
P-glycoprotein inhibitior	-	0.8111	81.11%
P-glycoprotein substrate	-	0.6394	63.94%
CYP3A4 substrate	+	0.6583	65.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.4793	47.93%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9306	93.06%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7871	78.71%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7869	78.69%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8125	81.25%
Androgen receptor binding	-	0.6170	61.70%
Thyroid receptor binding	+	0.5497	54.97%
Glucocorticoid receptor binding	+	0.5676	56.76%
Aromatase binding	-	0.5097	50.97%
PPAR gamma	+	0.6906	69.06%
Honey bee toxicity	-	0.7188	71.88%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7522	75.22%

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%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.19%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.85%	97.09%
CHEMBL4208	P20618	Proteasome component C5	94.25%	90.00%
CHEMBL2581	P07339	Cathepsin D	94.16%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.71%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.17%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.09%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.17%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.93%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.45%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.35%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.58%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.76%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.83%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.28%	99.17%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.85%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	85.55%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.78%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.19%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.83%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	80.72%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.72%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.72%	96.00%

Plants that contains it

• Citrus × aurantium
• Citrus deliciosa
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Micromeria graeca
• Minthostachys spicata

Cross-Links

• PubChem: 442456
• NPASS: NPC97285
• LOTUS: LTS0171172
• wikiData: Q3388129