Axillaroside

Details

• Internal ID: b201a55e-65c9-43d6-bc04-d72d1281d4d6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,6-dimethoxy-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)OC)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)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C23H24O13/c1-32-21-12(35-23-19(31)18(30)15(27)13(7-24)36-23)6-11-14(16(21)28)17(29)22(33-2)20(34-11)8-3-4-9(25)10(26)5-8/h3-6,13,15,18-19,23-28,30-31H,7H2,1-2H3/t13-,15-,18+,19-,23-/m1/s1
• InChI Key: FIBYVUGPMHIWTD-RODNGKRTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₃
• Molecular Weight: 508.40 g/mol
• Exact Mass: 508.12169082 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8855	88.55%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.5539	55.39%
OATP1B1 inhibitior	+	0.9292	92.92%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7245	72.45%
P-glycoprotein inhibitior	-	0.5950	59.50%
P-glycoprotein substrate	-	0.6449	64.49%
CYP3A4 substrate	+	0.6110	61.10%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
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	+	0.7958	79.58%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9125	91.25%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.5736	57.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4194	41.94%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9199	91.99%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8441	84.41%
Androgen receptor binding	+	0.6374	63.74%
Thyroid receptor binding	+	0.5775	57.75%
Glucocorticoid receptor binding	+	0.7506	75.06%
Aromatase binding	+	0.5329	53.29%
PPAR gamma	+	0.7195	71.95%
Honey bee toxicity	-	0.7688	76.88%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6649	66.49%
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	99.67%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.73%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.15%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.67%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.17%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.08%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.24%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.86%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.56%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.73%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.73%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.71%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.95%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.94%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.44%	96.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.35%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.20%	90.71%

Plants that contains it

• Achillea nana
• Aconitum napellus
• Astragalus bisulcatus
• Baccharoides lasiopus
• Bidens pilosa
• Boenninghausenia albiflora
• Bothriocline ripensis
• Brachyglottis bidwillii
• Calea lantanoides
• Chromolaena odorata
• Cibotium barometz
• Coronilla cretica
• Drosera indica
• Drummondita hassellii
• Ephedra distachya
• Flindersia xanthoxyla
• Galium mollugo
• Gardenia imperialis
• Gomesa radicans
• Grindelia scorzonerifolia
• Lepidium graminifolium
• Lonchocarpus atropurpureus
• Neurolaena macrocephala
• Pinus flexilis
• Psilotum nudum
• Rydingia limbata
• Santolina chamaecyparissus
• Senegalia mellifera
• Stizolophus coronopifolius
• Strychnos axillaris
• Typha latifolia
• Uncaria sterrophylla
• Vicia amoena

Cross-Links

• PubChem: 101243893
• NPASS: NPC25601
• LOTUS: LTS0200026
• wikiData: Q104995612