5-hydroxy-6,7-dimethoxy-2-[3-methoxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one

Details

• Internal ID: 2e490461-9d0c-4ba6-b7ff-9ff5d7489e42
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 5-hydroxy-6,7-dimethoxy-2-[3-methoxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)O)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O
• InChI: InChI=1S/C24H26O12/c1-31-14-6-10(4-5-12(14)35-24-22(30)21(29)19(27)17(9-25)36-24)13-7-11(26)18-15(34-13)8-16(32-2)23(33-3)20(18)28/h4-8,17,19,21-22,24-25,27-30H,9H2,1-3H3/t17-,19-,21+,22-,24-/m0/s1
• InChI Key: DESCMBTYIJAXJU-OPFYKBPPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆O₁₂
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.14242626 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.37
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5088	50.88%
Caco-2	-	0.8169	81.69%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6030	60.30%
OATP2B1 inhibitior	-	0.7130	71.30%
OATP1B1 inhibitior	+	0.7980	79.80%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7079	70.79%
P-glycoprotein inhibitior	+	0.6399	63.99%
P-glycoprotein substrate	-	0.5820	58.20%
CYP3A4 substrate	+	0.6091	60.91%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9371	93.71%
CYP2C9 inhibition	-	0.9410	94.10%
CYP2C19 inhibition	-	0.9438	94.38%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.9134	91.34%
CYP2C8 inhibition	+	0.7834	78.34%
CYP inhibitory promiscuity	-	0.7474	74.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7050	70.50%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9288	92.88%
Skin irritation	-	0.8406	84.06%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.5864	58.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4754	47.54%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9409	94.09%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9415	94.15%
Acute Oral Toxicity (c)	III	0.6685	66.85%
Estrogen receptor binding	+	0.8464	84.64%
Androgen receptor binding	+	0.6369	63.69%
Thyroid receptor binding	+	0.5997	59.97%
Glucocorticoid receptor binding	+	0.6900	69.00%
Aromatase binding	+	0.5795	57.95%
PPAR gamma	+	0.7321	73.21%
Honey bee toxicity	-	0.7346	73.46%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7549	75.49%
Fish aquatic toxicity	+	0.7605	76.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.28%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.77%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.36%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.54%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.47%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.85%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.43%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.19%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.13%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	89.32%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.34%	99.17%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.64%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	86.01%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.26%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.97%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.34%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.72%	90.71%
CHEMBL3194	P02766	Transthyretin	80.71%	90.71%

Plants that contains it

• Artemisia annua
• Artemisia capillaris
• Cirsium chinense
• Sium suave
• Thymus vulgaris

Cross-Links

• PubChem: 11972310
• NPASS: NPC125175
• LOTUS: LTS0183081
• wikiData: Q104977470