Xanthoxyletin

Details

• Internal ID: a7930edb-cd81-45d7-b186-e4ea8e285775
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Linear pyranocoumarins
• IUPAC Name: 5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C3C(=C2OC)C=CC(=O)O3)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C3C(=C2OC)C=CC(=O)O3)C
• InChI: InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3
• InChI Key: JSJIIHRNDMLJGK-UHFFFAOYSA-N
• Popularity: 58 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.99
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 84-99-1
• Xanthoxylin N
• 5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
• Xanthoxyloin
• UNII-69MPX4M5VD
• 69MPX4M5VD
• NSC 35542; Xanthoxylin N
• CHEBI:69929
• NSC 35542
• NSC-35542
• 5-Methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one
• XANTHOXYLETIN [MI]
• MLS000876794
• CHEMBL501358
• MEGxp0_001370
• SCHEMBL5793283
• ACon1_000545
• DTXSID70232891
• HMS2269F07
• HY-N1065
• NSC35542
• BDBM50428432
• AKOS032962595
• NCGC00168976-01
• NCI60_003203
• SMR000440571
• XX163678
• CS-0016348
• 5-methoxy-2,2-dimethyl-pyrano[3,2-g]chromen-8-one
• BRD-K28556256-001-01-3
• Q27138273
• 2H,2-b:5,4-b']dipyran-2-one, 5-methoxy-8,8-dimethyl-
• 2-Propenoic acid,2-dimethyl-2H-1-benzopyran-6-yl)-, .delta.-lactone
• 2H,8H-Benzo(1,2-b:5,4-b')dipyran-2-one, 5-methoxy-8,8-dimethyl-
• 5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9CI
• NCGC00168976-02!5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
• 7-HYDROXY-5-METHOXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-ACRYLIC ACID .DELTA.-LACTONE
• 7-Hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-acrylic Acid delta-Lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.9037	90.37%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6940	69.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9405	94.05%
OATP1B3 inhibitior	+	0.9755	97.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5243	52.43%
P-glycoprotein inhibitior	-	0.6307	63.07%
P-glycoprotein substrate	-	0.7980	79.80%
CYP3A4 substrate	+	0.5286	52.86%
CYP2C9 substrate	-	0.6755	67.55%
CYP2D6 substrate	-	0.8349	83.49%
CYP3A4 inhibition	+	0.5583	55.83%
CYP2C9 inhibition	-	0.7827	78.27%
CYP2C19 inhibition	+	0.6475	64.75%
CYP2D6 inhibition	-	0.7376	73.76%
CYP1A2 inhibition	+	0.6377	63.77%
CYP2C8 inhibition	-	0.6726	67.26%
CYP inhibitory promiscuity	+	0.6134	61.34%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Danger	0.5268	52.68%
Eye corrosion	-	0.9695	96.95%
Eye irritation	+	0.8496	84.96%
Skin irritation	-	0.7952	79.52%
Skin corrosion	-	0.9812	98.12%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7685	76.85%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.5949	59.49%
skin sensitisation	-	0.8176	81.76%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7470	74.70%
Acute Oral Toxicity (c)	III	0.4420	44.20%
Estrogen receptor binding	+	0.9557	95.57%
Androgen receptor binding	+	0.7085	70.85%
Thyroid receptor binding	+	0.6740	67.40%
Glucocorticoid receptor binding	+	0.7910	79.10%
Aromatase binding	+	0.9015	90.15%
PPAR gamma	+	0.8141	81.41%
Honey bee toxicity	-	0.8032	80.32%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9755	97.55%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	7710 nM	Ki	PMID: 22892213
CHEMBL3594	Q16790	Carbonic anhydrase IX	740 nM; 740 nM	Ki; Ki	PMID: 22892213; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	6270 nM	Ki	PMID: 22892213
CHEMBL3242	O43570	Carbonic anhydrase XII	960 nM; 960 nM	Ki; Ki	PMID: 22892213; via Super-PRED
CHEMBL3912	Q8N1Q1	Carbonic anhydrase XIII	3150 nM	Ki	PMID: 22892213
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 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	98.55%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.77%	94.45%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	92.92%	94.03%
CHEMBL2581	P07339	Cathepsin D	91.50%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.92%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.73%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.46%	89.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.69%	85.30%
CHEMBL1907	P15144	Aminopeptidase N	84.57%	93.31%
CHEMBL2535	P11166	Glucose transporter	84.10%	98.75%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.18%	80.96%
CHEMBL1871	P10275	Androgen Receptor	82.96%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.76%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.75%	93.99%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.99%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.79%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.03%	96.77%

Plants that contains it

• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Angelica archangelica
• Angelica taiwaniana
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Asterolasia squamuligera
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Catharanthus roseus
• Chloranthus tianmushanensis
• Chloroxylon swietenia
• Chromolaena odorata
• Chromolaena pulchella
• Cinnamomum chekiangense
• Citrus × aurantium
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Clausena anisata
• Clausena excavata
• Clausena harmandiana
• Clausena wallichii
• Cnidium monnieri
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Ficus formosana
• Gardenia fosbergii
• Geijera balansae
• Halfordia kendack
• Hansenia weberbaueriana
• Harrisonia perforata
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Lysimachia arvensis
• Moringa oleifera
• Murraya koenigii
• Odixia angusta
• Pastinaca sativa
• Peucedanum rubricaule
• Pleiospermium alatum
• Pleurospermum rivulorum
• Pluchea dioscoridis
• Plumbago zeylanica
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Pyrola rotundifolia
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Stevia alpina
• Taxodium huegelii
• Uncaria perrottetii
• Vitex madiensis
• Zanthoxylum americanum
• Zanthoxylum dipetalum
• Zanthoxylum sarasinii

Cross-Links

• PubChem: 66548
• NPASS: NPC154176
• ChEMBL: CHEMBL501358
• LOTUS: LTS0112626
• wikiData: Q27138273