Xanthone

Details

• Internal ID: 49fe5610-cd06-4527-9c27-052617b55748
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: xanthen-9-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3O2
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3O2
• InChI: InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
• InChI Key: JNELGWHKGNBSMD-UHFFFAOYSA-N
• Popularity: 3,399 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₂
• Molecular Weight: 196.20 g/mol
• Exact Mass: 196.052429494 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 9H-Xanthen-9-one
• 90-47-1
• Xanthen-9-one
• 9-Xanthenone
• Benzophenone oxide
• 9-Oxoxanthene
• Xanthenone
• Genicide
• 9-Xanthone
• Diphenylene ketone oxide
• Dibenzo-gamma-pyrone
• 9H-Xanthene, 9-oxo-
• Xanthene, 9-oxo-
• Caswell No. 905
• Dibenzo-.gamma.-pyrone
• NSC 14978
• EINECS 201-997-7
• MFCD00005060
• EPA Pesticide Chemical Code 086503
• UNII-9749WEV0CA
• AI3-00077
• 9749WEV0CA
• CHEMBL186784
• E 6
• DTXSID6021795
• CHEBI:37647
• C13H8O2
• NSC14978
• NSC-14978
• diphenyline ketone oxide
• xanthene-9-one
• xanthen-9-on
• Xanthone (Genicide)
• Xanthone, 97%
• ST024714
• XANTHONE [MI]
• Spectrum2_000052
• Spectrum3_001884
• XANTHONE [USP-RS]
• SCHEMBL41161
• BSPBio_003388
• SPECTRUM200523
• MLS002207109
• SPBio_000203
• ghl.PD_Mitscher_leg0.1212
• DTXCID201795
• KBio3_002891
• WLN: T C666 BO IVJ
• HMS3651G22
• BCP21155
• HY-N0126
• STR05546
• Tox21_301151
• BDBM50155411
• CCG-38356
• s2372
• STK372481
• AKOS001213782
• SDCCGMLS-0066462.P001
• CAS-90-47-1
• NCGC00095484-01
• NCGC00095484-02
• NCGC00095484-03
• NCGC00255049-01
• SMR000112239
• SY017687
• LS-162426
• CS-0007833
• FT-0645039
• SW219800-1
• X0005
• EN300-20176
• F15407
• A843557
• AC-907/21098006
• Q421789
• SR-05000002437
• SR-05000002437-1
• W-100331
• F8889-9282
• Z104477176
• Xanthone, United States Pharmacopeia (USP) Reference Standard
• InChI=1/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8
• N-methyl-1-[5-({[(4-methylbenzyl)amino]carbonyl}amino)pyridin-2-yl]piperidine-4-carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.7883	78.83%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8714	87.14%
Subcellular localzation	Mitochondria	0.4724	47.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9419	94.19%
OATP1B3 inhibitior	+	0.9930	99.30%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6663	66.63%
P-glycoprotein inhibitior	-	0.8025	80.25%
P-glycoprotein substrate	-	0.9820	98.20%
CYP3A4 substrate	-	0.6643	66.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8049	80.49%
CYP3A4 inhibition	-	0.5090	50.90%
CYP2C9 inhibition	-	0.7391	73.91%
CYP2C19 inhibition	+	0.8617	86.17%
CYP2D6 inhibition	-	0.8970	89.70%
CYP1A2 inhibition	+	0.9854	98.54%
CYP2C8 inhibition	-	0.9612	96.12%
CYP inhibitory promiscuity	-	0.6084	60.84%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9213	92.13%
Carcinogenicity (trinary)	Warning	0.4820	48.20%
Eye corrosion	-	0.8532	85.32%
Eye irritation	+	0.9794	97.94%
Skin irritation	+	0.8129	81.29%
Skin corrosion	-	0.9878	98.78%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.8123	81.23%
Micronuclear	+	0.7059	70.59%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.5865	58.65%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	+	0.6000	60.00%
Acute Oral Toxicity (c)	III	0.5082	50.82%
Estrogen receptor binding	+	0.8838	88.38%
Androgen receptor binding	+	0.6576	65.76%
Thyroid receptor binding	+	0.6554	65.54%
Glucocorticoid receptor binding	+	0.7350	73.50%
Aromatase binding	+	0.8755	87.55%
PPAR gamma	+	0.7049	70.49%
Honey bee toxicity	-	0.9118	91.18%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.6570	65.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	31622.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	35481.3 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	25118.9 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	22387.2 nM	Potency	via CMAUP
CHEMBL1951	P21397	Monoamine oxidase A	840 nM	IC50	PMID: 15482934
CHEMBL1293232	Q16637	Survival motor neuron protein	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.43%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.06%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.44%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.80%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.52%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%

Plants that contains it

• Calophyllum pinetorum
• Garcinia mangostana
• Harungana madagascariensis
• Hypericum perforatum
• Maclura cochinchinensis
• Rhachidosorus mesosorus

Cross-Links

• PubChem: 7020
• NPASS: NPC35744
• ChEMBL: CHEMBL186784
• LOTUS: LTS0088534
• wikiData: Q421789