5-hydroxy-2-methyl-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]benzo[g]chromen-4-one

Details

• Internal ID: 84c09f53-e8f0-4c27-bd2c-e71e5161d861
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones > Naphthopyranone glycosides
• IUPAC Name: 5-hydroxy-2-methyl-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]benzo[g]chromen-4-one
• InChI: InChI=1S/C21H22O9/c1-9-5-12(23)16-13(29-9)6-10-3-2-4-11(15(10)18(16)25)8-28-21-20(27)19(26)17(24)14(7-22)30-21/h2-6,14,17,19-22,24-27H,7-8H2,1H3/t14-,17-,19+,20-,21-/m1/s1
• InChI Key: HWOPCYBADKWVEI-IAAKTDFRSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₉
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.12638228 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.28
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6673	66.73%
Caco-2	-	0.8203	82.03%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6320	63.20%
OATP2B1 inhibitior	-	0.5607	56.07%
OATP1B1 inhibitior	+	0.8715	87.15%
OATP1B3 inhibitior	+	0.9717	97.17%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5224	52.24%
P-glycoprotein inhibitior	-	0.7069	70.69%
P-glycoprotein substrate	-	0.7673	76.73%
CYP3A4 substrate	+	0.6250	62.50%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9604	96.04%
CYP2C9 inhibition	-	0.9542	95.42%
CYP2C19 inhibition	-	0.9251	92.51%
CYP2D6 inhibition	-	0.9462	94.62%
CYP1A2 inhibition	-	0.9100	91.00%
CYP2C8 inhibition	+	0.4503	45.03%
CYP inhibitory promiscuity	-	0.8072	80.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6171	61.71%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9499	94.99%
Skin irritation	-	0.8389	83.89%
Skin corrosion	-	0.9692	96.92%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6235	62.35%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9230	92.30%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.5938	59.38%
Acute Oral Toxicity (c)	III	0.6211	62.11%
Estrogen receptor binding	+	0.7738	77.38%
Androgen receptor binding	+	0.6652	66.52%
Thyroid receptor binding	-	0.6219	62.19%
Glucocorticoid receptor binding	+	0.7120	71.20%
Aromatase binding	+	0.6984	69.84%
PPAR gamma	+	0.6721	67.21%
Honey bee toxicity	-	0.8203	82.03%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.7000	70.00%

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	99.24%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	98.01%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	96.35%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.91%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.69%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.28%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.39%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.39%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.17%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.21%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.98%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.20%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	83.94%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.91%	99.15%
CHEMBL1937	Q92769	Histone deacetylase 2	80.37%	94.75%

Plants that contains it

• Senna obtusifolia

Cross-Links

• PubChem: 5315728
• LOTUS: LTS0144386
• wikiData: Q105034754