Xyloidone

Details

• Internal ID: 0610f956-ebd8-4fc4-9f26-462c7aaf52ee
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 2,2-dimethylbenzo[g]chromene-5,10-dione
• SMILES (Canonical): CC1(C=CC2=C(O1)C(=O)C3=CC=CC=C3C2=O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C(=O)C3=CC=CC=C3C2=O)C
• InChI: InChI=1S/C15H12O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-8H,1-2H3
• InChI Key: OWFHAMHRUCUSRM-UHFFFAOYSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25 g/mol
• Exact Mass: 240.078644241 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Dehydro-alpha-lapachone
• 15297-92-4
• Dehydrolapachone
• 2,2-dimethylbenzo[g]chromene-5,10-dione
• Dehydro-.alpha.-lapachol
• Dehydro-.alpha.-lapacone
• Dehydro-.alpha.-lapachone
• Xyloidone (VAN)
• .alpha.-Lapachone, dehydro-
• 2,2-Dimethyl-2H-benzo[g]chromene-5,10-dione
• Dehydro-alpha-lapachol
• Dehydro-alpha-lapacone
• DEHYDROPLAPACHONE
• 2H-Naphtho[2,3-b]pyran-5,10-dione, 2,2-dimethyl-
• NSC106453
• NSC629748
• alpha-Lapachone, dehydro-
• NSC 106453
• NSC 629748
• 305WY61CUF
• LDN-22684
• NSC-106453
• NSC-629748
• 2H-Naphtho(2,3-b)pyran-5,10-dione, 2,2-dimethyl-
• 2H-Naphtho(2,3-b)pyran-5,10-dione, 2,2-dimethyl- (8CI)(9CI)
• LDN 22684; NSC 106453; NSC 629748; Xiloidone; Xyloidone; alpha-Lapachone, dehydro-
• XILOIDONE
• D08YHA
• Allyl 3-aminopropylcarbamate
• UNII-305WY61CUF
• CHEMBL272253
• SCHEMBL3617968
• 2,2-dimethyl-2H,5H,10H-benzo[g]chromene-5,10-dione
• BDBM24786
• DTXSID30165176
• OWFHAMHRUCUSRM-UHFFFAOYSA-N
• Pyranonaphthoquinone derivative, 23
• MFCD00022286
• AKOS024341158
• 2H-Naphtho[2,10-dione, 2,2-dimethyl-
• FT-0702603
• 2,2-dimethyl-2h-benzo [g]chromene-5,10-dione
• 2,2-Dimethyl-2H-benzo[g]chromene-5,10-dione #
• 2,2-DIMETHYL-2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE
• Q 99 2,2-DIMETHYL-2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE
• LDN 22684; NSC 106453; NSC 629748; Xiloidone; Xyloidone; -Lapachone, dehydro-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.7275	72.75%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7943	79.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9313	93.13%
OATP1B3 inhibitior	+	0.9819	98.19%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5545	55.45%
P-glycoprotein inhibitior	-	0.8029	80.29%
P-glycoprotein substrate	-	0.9518	95.18%
CYP3A4 substrate	+	0.5069	50.69%
CYP2C9 substrate	-	0.8096	80.96%
CYP2D6 substrate	-	0.8499	84.99%
CYP3A4 inhibition	-	0.6466	64.66%
CYP2C9 inhibition	+	0.8661	86.61%
CYP2C19 inhibition	+	0.8175	81.75%
CYP2D6 inhibition	+	0.5000	50.00%
CYP1A2 inhibition	+	0.7557	75.57%
CYP2C8 inhibition	-	0.9056	90.56%
CYP inhibitory promiscuity	+	0.7849	78.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9518	95.18%
Carcinogenicity (trinary)	Non-required	0.6102	61.02%
Eye corrosion	-	0.9602	96.02%
Eye irritation	+	0.9115	91.15%
Skin irritation	-	0.6313	63.13%
Skin corrosion	-	0.9239	92.39%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5487	54.87%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.6977	69.77%
skin sensitisation	+	0.5233	52.33%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7560	75.60%
Acute Oral Toxicity (c)	III	0.6385	63.85%
Estrogen receptor binding	+	0.9225	92.25%
Androgen receptor binding	+	0.6196	61.96%
Thyroid receptor binding	-	0.5197	51.97%
Glucocorticoid receptor binding	-	0.5601	56.01%
Aromatase binding	+	0.6456	64.56%
PPAR gamma	+	0.5754	57.54%
Honey bee toxicity	-	0.8494	84.94%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9453	94.53%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	214 nM; 214 nM	IC50; IC50	PMID: 18318466; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.33%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	91.90%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	90.84%	94.73%
CHEMBL2581	P07339	Cathepsin D	89.92%	98.95%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.04%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.97%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.11%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.28%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.21%	91.11%
CHEMBL2039	P27338	Monoamine oxidase B	82.00%	92.51%
CHEMBL1907	P15144	Aminopeptidase N	81.76%	93.31%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.59%	82.69%

Plants that contains it

• Handroanthus chrysotrichus
• Handroanthus guayacan
• Handroanthus impetiginosus
• Kigelia africana subsp. africana
• Markhamia stipulata
• Newbouldia laevis
• Radermachera sinica
• Rhinacanthus nasutus
• Rubia cordifolia
• Stereospermum kunthianum
• Tabebuia rosea
• Tecomella undulata
• Tectona grandis

Cross-Links

• PubChem: 72734
• NPASS: NPC291799
• ChEMBL: CHEMBL272253
• LOTUS: LTS0218690
• wikiData: Q72461887