Apiin

Details

• Internal ID: 95be8a4a-e8a5-4e8e-9e48-dd051a75c4f0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)(CO)O
• InChI: InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1
• InChI Key: NTDLXWMIWOECHG-YRCFQSNFSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.49
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 26544-34-3
• Apigenin-7-apioglucoside
• Apioside
• UNII-6QU3EZE37U
• 6QU3EZE37U
• CHEBI:15932
• EINECS 247-780-0
• 7-((2-O-beta-D-Apiofuranosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone
• Apigenin 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]
• 7-O-(beta-D-Apiofuranosyl-1,2-beta-D-glucosyl)-5,7,4'-trihydroxyflavone
• 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 3-C-(hydroxymethyl)-beta-D-glycero-tetrofuranosyl-(1->2)-beta-D-glucopyranoside
• 7-(((2S,3R,4S,5S,6R)-3-(((2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• 5,7,4'-trihydroxyflavone 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]
• 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-beta-D-glucopyranoside
• 7-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one
• apigenin 7-O-(beta-D-apiosyl-(1->2)-beta-D-glucoside)
• C26H28O14
• 5,7,4'-trihydroxyflavone 7-O-(beta-D-apiosyl-(1->2)-beta-D-glucoside)
• 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)-beta-D-glucopyranoside
• 7-((2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one
• 7-((2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 7-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• Spectrum_000204
• SpecPlus_000939
• Apiin (11)
• Spectrum2_001800
• Spectrum3_001787
• Spectrum4_001817
• Spectrum5_000553
• APIIN [MI]
• BSPBio_003313
• KBioGR_002458
• KBioSS_000684
• SPECTRUM350025
• 7-O-(beta-D-apiofuranosyl-(1-2)-beta-D-glucosyl)-apigenin
• MLS000575008
• DivK1c_007035
• SCHEMBL316910
• SPBio_001759
• CHEMBL1535342
• KBio1_001979
• KBio2_000684
• KBio2_003252
• KBio2_005820
• KBio3_002815
• DTXSID90949393
• 7-O-(beta-D-apiofuranosyl-(1-2)-beta-D-glucosyl)-5,7,4'-trihydroxyflavone
• NTDLXWMIWOECHG-YRCFQSNFSA-N
• BDBM153268
• HMS2209P05
• 4H-1-Benzopyran-4-one, 7-[(2-O-D-apio-.beta.-D-furanosyl-.beta.-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-
• HY-N0577
• CCG-39950
• AKOS030632988
• SDCCGMLS-0066949.P001
• NCGC00178147-01
• AS-74876
• SMR000156232
• CS-0009113
• C04858
• SR-01000712126
• Q2858300
• SR-01000712126-2
• BRD-K52379519-001-02-0
• 4H-1-Benzopyran-4-one, 7-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-
• 7-((2-O-.BETA.-D-APIOFURANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-5- HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRANONE
• 7-((2-O-D-APIO-.BETA.-D-FURANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)- 5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• 7-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5874	58.74%
Caco-2	-	0.9055	90.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6429	64.29%
OATP2B1 inhibitior	-	0.5590	55.90%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7563	75.63%
P-glycoprotein inhibitior	-	0.5553	55.53%
P-glycoprotein substrate	-	0.6031	60.31%
CYP3A4 substrate	+	0.6688	66.88%
CYP2C9 substrate	-	0.8271	82.71%
CYP2D6 substrate	-	0.8606	86.06%
CYP3A4 inhibition	-	0.8440	84.40%
CYP2C9 inhibition	-	0.9319	93.19%
CYP2C19 inhibition	-	0.8680	86.80%
CYP2D6 inhibition	-	0.9030	90.30%
CYP1A2 inhibition	-	0.9212	92.12%
CYP2C8 inhibition	+	0.6915	69.15%
CYP inhibitory promiscuity	-	0.8119	81.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5235	52.35%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.8079	80.79%
Skin corrosion	-	0.9542	95.42%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4268	42.68%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7899	78.99%
Acute Oral Toxicity (c)	III	0.5720	57.20%
Estrogen receptor binding	+	0.8155	81.55%
Androgen receptor binding	+	0.7109	71.09%
Thyroid receptor binding	+	0.5499	54.99%
Glucocorticoid receptor binding	+	0.5849	58.49%
Aromatase binding	+	0.7892	78.92%
PPAR gamma	+	0.8280	82.80%
Honey bee toxicity	-	0.6406	64.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7344	73.44%

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	99.72%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.22%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.90%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.42%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.41%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.34%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	93.63%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.83%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.45%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.25%	83.57%
CHEMBL1951	P21397	Monoamine oxidase A	92.07%	91.49%
CHEMBL242	Q92731	Estrogen receptor beta	91.73%	98.35%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.16%	95.89%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	88.91%	96.69%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.66%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.12%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.18%	95.83%
CHEMBL3194	P02766	Transthyretin	84.10%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.00%	90.71%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.75%	80.33%
CHEMBL4530	P00488	Coagulation factor XIII	83.74%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.58%	99.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.23%	95.78%
CHEMBL3401	O75469	Pregnane X receptor	81.64%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.44%	96.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.25%	95.89%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.98%	95.53%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.23%	97.36%
CHEMBL220	P22303	Acetylcholinesterase	80.04%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.01%	92.94%

Plants that contains it

• Ageratina calophylla
• Apium graveolens
• Atroxima liberica
• Bergenia crassifolia
• Castanopsis eyrei
• Centaurea cyanus
• Christisonia bicolor
• Convallaria majalis
• Corynanthe pachyceras
• Crotalaria micans
• Crotalaria orixensis
• Elsholtzia rugulosa
• Eucalyptus decorticans
• Euryops rupestris
• Holarrhena pubescens
• Hymenophyllum nephrophyllum
• Hypericum carinatum
• Isodon angustifolius
• Isodon loxothyrsus
• Laetia corymbulosa
• Lawsonia inermis
• Licaria brasiliensis
• Limonium axillare
• Linum salsoloides
• Litsea verticillata
• Monarda punctata
• Palafoxia texana
• Persicaria mitis
• Petroselinum crispum
• Reynoutria japonica
• Sanguisorba officinalis
• Scutellaria sieberi
• Smilax bracteata
• Tynanthus panurensis
• Vepris nobilis

Cross-Links

• PubChem: 5280746
• NPASS: NPC122809
• ChEMBL: CHEMBL1535342
• LOTUS: LTS0178138
• wikiData: Q2858300