apigenin-7-O-gentiobioside

Details

• Internal ID: 6b1d8f92-c4a7-4b02-8734-3a2a81ba9870
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c28-8-17-20(32)22(34)24(36)26(41-17)38-9-18-21(33)23(35)25(37)27(42-18)39-12-5-13(30)19-14(31)7-15(40-16(19)6-12)10-1-3-11(29)4-2-10/h1-7,17-18,20-30,32-37H,8-9H2/t17-,18-,20-,21-,22+,23+,24-,25-,26-,27-/m1/s1
• InChI Key: XDMJJZUUHWWITI-IPOZFMEPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.13
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• apigenin 7-O-gentiobioside
• CHEBI:145768
• apigenin 7-O-Glc-(1->6)-Glc
• 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
• 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• 5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-one
• RefChem:113403
• SCHEMBL30282307

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6238	62.38%
Caco-2	-	0.9227	92.27%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6259	62.59%
OATP2B1 inhibitior	-	0.5588	55.88%
OATP1B1 inhibitior	+	0.9370	93.70%
OATP1B3 inhibitior	+	0.9578	95.78%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7500	75.00%
P-glycoprotein inhibitior	-	0.7076	70.76%
P-glycoprotein substrate	-	0.7148	71.48%
CYP3A4 substrate	+	0.5710	57.10%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9399	93.99%
CYP2C9 inhibition	-	0.9431	94.31%
CYP2C19 inhibition	-	0.9201	92.01%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.9283	92.83%
CYP2C8 inhibition	+	0.7201	72.01%
CYP inhibitory promiscuity	-	0.7667	76.67%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6368	63.68%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9118	91.18%
Skin irritation	-	0.8293	82.93%
Skin corrosion	-	0.9710	97.10%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3854	38.54%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.8696	86.96%
skin sensitisation	-	0.9266	92.66%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7601	76.01%
Acute Oral Toxicity (c)	IV	0.4161	41.61%
Estrogen receptor binding	+	0.7517	75.17%
Androgen receptor binding	+	0.6205	62.05%
Thyroid receptor binding	-	0.5237	52.37%
Glucocorticoid receptor binding	-	0.5444	54.44%
Aromatase binding	+	0.6198	61.98%
PPAR gamma	+	0.7485	74.85%
Honey bee toxicity	-	0.6986	69.86%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.7469	74.69%

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	99.45%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.00%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.32%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.85%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.14%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.90%	86.92%
CHEMBL3194	P02766	Transthyretin	92.47%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.42%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.82%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	89.54%	91.49%
CHEMBL242	Q92731	Estrogen receptor beta	89.35%	98.35%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.34%	83.57%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.46%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.13%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.12%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.83%	96.21%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.79%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.28%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.91%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.87%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.77%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.29%	95.83%
CHEMBL220	P22303	Acetylcholinesterase	80.13%	94.45%

Plants that contains it

• Artemisia judaica
• Asystasia gangetica
• Halenia elliptica
• Helichrysum arenarium
• Lonicera gracilipes
• Scorzonera laciniata
• Trachelospermum jasminoides

Cross-Links

• PubChem: 10841200
• NPASS: NPC3228
• LOTUS: LTS0121298
• wikiData: Q76416029