1,5-Dihydroxyxanthone

Details

• Internal ID: 0b9fb4c7-c19d-444d-b533-b809cca2e596
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,5-dihydroxyxanthen-9-one
• SMILES (Canonical): C1=CC2=C(C(=C1)O)OC3=CC=CC(=C3C2=O)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)OC3=CC=CC(=C3C2=O)O
• InChI: InChI=1S/C13H8O4/c14-8-4-2-6-10-11(8)12(16)7-3-1-5-9(15)13(7)17-10/h1-6,14-15H
• InChI Key: APIPFXZYOMIJQG-UHFFFAOYSA-N
• Popularity: 40 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₄
• Molecular Weight: 228.20 g/mol
• Exact Mass: 228.04225873 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 14686-65-8
• 1,5-dihydroxyxanthen-9-one
• 1,5-DIHYDROXY-9H-XANTHEN-9-ONE
• 9H-Xanthen-9-one, 1,5-dihydroxy-
• CHEMBL185686
• 1,5-Dihydroxy-xanthen-9-one
• SCHEMBL15527312
• DTXSID80420489
• BDBM50155419
• 1,5-Dihydroxy-9H-xanthen-9-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9717	97.17%
Caco-2	-	0.7016	70.16%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6458	64.58%
OATP2B1 inhibitior	-	0.6993	69.93%
OATP1B1 inhibitior	+	0.9352	93.52%
OATP1B3 inhibitior	+	0.9836	98.36%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7675	76.75%
P-glycoprotein inhibitior	-	0.8465	84.65%
P-glycoprotein substrate	-	0.9430	94.30%
CYP3A4 substrate	-	0.5607	56.07%
CYP2C9 substrate	-	0.6265	62.65%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	+	0.5297	52.97%
CYP2C9 inhibition	+	0.5447	54.47%
CYP2C19 inhibition	-	0.6827	68.27%
CYP2D6 inhibition	-	0.9006	90.06%
CYP1A2 inhibition	+	0.9448	94.48%
CYP2C8 inhibition	-	0.8591	85.91%
CYP inhibitory promiscuity	-	0.6121	61.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5084	50.84%
Eye corrosion	-	0.9693	96.93%
Eye irritation	+	0.9733	97.33%
Skin irritation	+	0.6448	64.48%
Skin corrosion	-	0.9838	98.38%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9088	90.88%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8100	81.00%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.5841	58.41%
Acute Oral Toxicity (c)	III	0.6516	65.16%
Estrogen receptor binding	+	0.7657	76.57%
Androgen receptor binding	-	0.5275	52.75%
Thyroid receptor binding	+	0.6547	65.47%
Glucocorticoid receptor binding	+	0.9038	90.38%
Aromatase binding	+	0.8598	85.98%
PPAR gamma	+	0.8916	89.16%
Honey bee toxicity	-	0.9389	93.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7742	77.42%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1951	P21397	Monoamine oxidase A	730 nM	IC50	PMID: 15482934

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.51%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.18%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.47%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.13%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.98%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.84%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	89.08%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.27%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.14%	94.45%
CHEMBL3959	P16083	Quinone reductase 2	81.76%	89.49%
CHEMBL2535	P11166	Glucose transporter	80.23%	98.75%

Plants that contains it

• Agasthiyamalaia pauciflora
• Allanblackia floribunda
• Allanblackia gabonensis
• Artemisia anomala
• Calophyllum apetalum
• Calophyllum bracteatum
• Calophyllum caledonicum
• Calophyllum inophyllum
• Calophyllum pulcherrimum
• Calophyllum tomentosum
• Crocus sieberi
• Eugenia myrcianthes
• Eupatorium glehnii
• Garcinia afzelii
• Garcinia gardneriana
• Garcinia linii
• Garcinia subelliptica
• Gynochthodes officinalis
• Jacobaea persoonii
• Leptochloa digitata
• Mammea americana
• Mammea odorata
• Mesua ferrea
• Montanoa karwinskii
• Pentadesma butyracea
• Pinus heldreichii
• Piper umbellatum
• Salix babylonica
• Senecio brasiliensis
• Strychnos decussata
• Tovomita krukovii
• Verbena bonariensis

Cross-Links

• PubChem: 5480299
• NPASS: NPC59551
• ChEMBL: CHEMBL185686
• LOTUS: LTS0052188
• wikiData: Q82231778