7-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-3,5-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one

Details

• Internal ID: 3b898e5d-e6c5-4a91-b412-923f6fbe4f9b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3,5-dihydroxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O12/c1-6-14(25)17(28)19(30)21(31-6)32-8-4-9(22)13-12(5-8)33-20(18(29)16(13)27)7-2-10(23)15(26)11(24)3-7/h2-6,14,17,19,21-26,28-30H,1H3/t6-,14-,17+,19+,21-/m0/s1
• InChI Key: LPEPTRFUOKMJCH-YDOQJWOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09547607 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.19
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 3

Synonyms

• 184533-14-0
• 7-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-3,5-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8357	83.57%
Caco-2	-	0.8883	88.83%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	+	0.5959	59.59%
OATP1B1 inhibitior	+	0.9091	90.91%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5351	53.51%
P-glycoprotein inhibitior	-	0.6809	68.09%
P-glycoprotein substrate	-	0.6020	60.20%
CYP3A4 substrate	+	0.5973	59.73%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.5306	53.06%
CYP2C8 inhibition	+	0.7599	75.99%
CYP inhibitory promiscuity	-	0.5648	56.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8520	85.20%
Skin irritation	-	0.6220	62.20%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.5699	56.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.4523	45.23%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.7072	70.72%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8665	86.65%
Acute Oral Toxicity (c)	III	0.5184	51.84%
Estrogen receptor binding	+	0.6918	69.18%
Androgen receptor binding	+	0.5847	58.47%
Thyroid receptor binding	+	0.5606	56.06%
Glucocorticoid receptor binding	+	0.6467	64.67%
Aromatase binding	-	0.5475	54.75%
PPAR gamma	+	0.6995	69.95%
Honey bee toxicity	-	0.8183	81.83%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5550	55.50%
Fish aquatic toxicity	+	0.9457	94.57%

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	99.59%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.39%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.46%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.31%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.67%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.58%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.86%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.32%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.62%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.25%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.91%	90.71%
CHEMBL3194	P02766	Transthyretin	87.72%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.93%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.62%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.44%	96.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.87%	94.42%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.96%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.25%	97.09%

Plants that contains it

• Alyxia reinwardtii
• Centaurea linifolia
• Cneoridium dumosum
• Leuzea centauroides
• Limonium gmelinii
• Machilus glaucescens
• Microtropis fokienensis
• Myrsine africana
• Thymus vulgaris
• Vitellaria paradoxa

Cross-Links

• PubChem: 102444976
• NPASS: NPC278348
• LOTUS: LTS0070667
• wikiData: Q105155135