Mesuaxanthone A

Details

• Internal ID: 43f3957c-de8b-43ab-9d61-a7eb608f4357
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,5-dihydroxy-3-methoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C2=O)C=CC=C3O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C2=O)C=CC=C3O)O
• InChI: InChI=1S/C14H10O5/c1-18-7-5-10(16)12-11(6-7)19-14-8(13(12)17)3-2-4-9(14)15/h2-6,15-16H,1H3
• InChI Key: IQIGECASJMDDMD-UHFFFAOYSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₅
• Molecular Weight: 258.23 g/mol
• Exact Mass: 258.05282342 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 3561-81-7
• 1,5-Dihydroxy-3-methoxyxanthone
• 9H-Xanthen-9-one, 1,5-dihydroxy-3-methoxy-
• 1,5-Dihydroxy-3-methoxy-9H-xanthen-9-one
• 1,5-dihydroxy-3-methoxyxanthen-9-one
• CHEMBL363747
• 1,5-Dihydroxy-3-methoxy-xanthen-9-one
• CHEBI:6785
• C10081
• MesuaxanthoneA
• 1,5-Dihydroxy-3-methoxyxanthone; 1,5-Hydroxy-3-methoxyxanthone
• AC1NQYTG
• DTXSID80189084
• HY-N3295
• BDBM50155425
• AKOS028108771
• 3-Methoxy-1,5-dihydroxyxanthen-9-one
• CS-0023832
• Q27107331
• B0005-179512

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9733	97.33%
Caco-2	-	0.5182	51.82%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7066	70.66%
OATP2B1 inhibitior	-	0.6982	69.82%
OATP1B1 inhibitior	+	0.9379	93.79%
OATP1B3 inhibitior	+	0.9925	99.25%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6842	68.42%
P-glycoprotein inhibitior	-	0.5667	56.67%
P-glycoprotein substrate	-	0.8749	87.49%
CYP3A4 substrate	+	0.5601	56.01%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5248	52.48%
CYP2C9 inhibition	-	0.5620	56.20%
CYP2C19 inhibition	+	0.6608	66.08%
CYP2D6 inhibition	-	0.7551	75.51%
CYP1A2 inhibition	+	0.9602	96.02%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.5452	54.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4815	48.15%
Eye corrosion	-	0.9346	93.46%
Eye irritation	+	0.9490	94.90%
Skin irritation	-	0.5868	58.68%
Skin corrosion	-	0.9760	97.60%
Ames mutagenesis	+	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8176	81.76%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9346	93.46%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7528	75.28%
Acute Oral Toxicity (c)	III	0.9071	90.71%
Estrogen receptor binding	+	0.7851	78.51%
Androgen receptor binding	+	0.8121	81.21%
Thyroid receptor binding	+	0.6826	68.26%
Glucocorticoid receptor binding	+	0.9375	93.75%
Aromatase binding	+	0.8513	85.13%
PPAR gamma	+	0.8763	87.63%
Honey bee toxicity	-	0.9119	91.19%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.6561	65.61%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1951	P21397	Monoamine oxidase A	40 nM	IC50	PMID: 15482934

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.69%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.53%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.21%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.01%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.42%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.83%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.76%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.62%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	92.22%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.13%	89.00%
CHEMBL2535	P11166	Glucose transporter	91.58%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.23%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.24%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.21%	91.49%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.18%	93.65%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.57%	99.17%
CHEMBL1907	P15144	Aminopeptidase N	85.01%	93.31%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.61%	95.50%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.37%	100.00%

Plants that contains it

• Agasthiyamalaia pauciflora
• Calophyllum caledonicum
• Canscora alata
• Chironia krebsii
• Garcinia linii
• Garcinia subelliptica
• Garcinia xanthochymus
• Haploclathra leiantha
• Haploclathra paniculata
• Hypericum monogynum
• Kielmeyera rupestris
• Kielmeyera speciosa
• Mesua ferrea
• Monnina salicifolia
• Schenkia spicata

Cross-Links

• PubChem: 5281651
• NPASS: NPC29231
• ChEMBL: CHEMBL363747
• LOTUS: LTS0060624
• wikiData: Q27107331