Xanthatin-1,5beta-epoxide (4)

Details

• Internal ID: 9bb45900-c3da-4df9-82ff-4c5eb5c9e441
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (1R,3S,5S,6S,8S)-6-methyl-11-methylidene-5-[(E)-3-oxobut-1-enyl]-4,9-dioxatricyclo[6.3.0.03,5]undecan-10-one
• SMILES (Canonical): CC1CC2C(CC3C1(O3)C=CC(=O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@H](C[C@H]3[C@@]1(O3)/C=C/C(=O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H18O4/c1-8-6-12-11(10(3)14(17)18-12)7-13-15(8,19-13)5-4-9(2)16/h4-5,8,11-13H,3,6-7H2,1-2H3/b5-4+/t8-,11+,12-,13-,15+/m0/s1
• InChI Key: NGAVJIMZMAIVPV-SOFYJNGRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 55.90 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• BDBM233120

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	+	0.5374	53.74%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6291	62.91%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9134	91.34%
OATP1B3 inhibitior	+	0.9374	93.74%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8772	87.72%
P-glycoprotein inhibitior	-	0.8350	83.50%
P-glycoprotein substrate	-	0.7740	77.40%
CYP3A4 substrate	+	0.5881	58.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	-	0.7171	71.71%
CYP2C9 inhibition	-	0.8717	87.17%
CYP2C19 inhibition	-	0.8578	85.78%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	-	0.5848	58.48%
CYP2C8 inhibition	-	0.7864	78.64%
CYP inhibitory promiscuity	-	0.9280	92.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8860	88.60%
Carcinogenicity (trinary)	Non-required	0.5506	55.06%
Eye corrosion	-	0.9682	96.82%
Eye irritation	-	0.8537	85.37%
Skin irritation	-	0.6237	62.37%
Skin corrosion	-	0.8845	88.45%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4835	48.35%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6772	67.72%
skin sensitisation	-	0.5751	57.51%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6256	62.56%
Acute Oral Toxicity (c)	III	0.5064	50.64%
Estrogen receptor binding	+	0.7313	73.13%
Androgen receptor binding	+	0.5251	52.51%
Thyroid receptor binding	+	0.5818	58.18%
Glucocorticoid receptor binding	+	0.7443	74.43%
Aromatase binding	-	0.6319	63.19%
PPAR gamma	-	0.5579	55.79%
Honey bee toxicity	-	0.7804	78.04%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9919	99.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.68%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.61%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	90.04%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.93%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.57%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.92%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.90%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.24%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.20%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	81.84%	91.19%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	80.64%	88.84%

Plants that contains it

• Xanthium spinosum
• Xanthium strumarium

Cross-Links

• PubChem: 14633040
• LOTUS: LTS0029703
• wikiData: Q105178815