Versicolactone A

Details

• Internal ID: 0e716d26-0137-45aa-9cb9-e406f522868e
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (4E,8E)-5,9-dimethyl-12-oxabicyclo[9.2.1]tetradeca-1(14),4,8-trien-13-one
• SMILES (Canonical): CC1=CCCC2=CC(CC(=CCC1)C)OC2=O
• SMILES (Isomeric): C/C/1=C\CCC2=CC(C/C(=C/CC1)/C)OC2=O
• InChI: InChI=1S/C15H20O2/c1-11-5-3-7-12(2)9-14-10-13(8-4-6-11)15(16)17-14/h6-7,10,14H,3-5,8-9H2,1-2H3/b11-6+,12-7+
• InChI Key: JOQILOMKLDOWGX-GNXRPPCSSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.69
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Neo-aristolactone
• 136315-17-8
• Neoaristolactone
• (4E,8E)-5,9-DIMETHYL-12-OXABICYCLO[9.2.1]TETRADECA-1(14),4,8-TRIEN-13-ONE
• 12-Oxabicyclo(9.2.1)tetradeca-1(14),4,8-trien-13-one, 5,9-dimethyl-, (E,E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9062	90.62%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Plasma membrane	0.3950	39.50%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.9573	95.73%
OATP1B3 inhibitior	+	0.9624	96.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.5321	53.21%
P-glycoprotein inhibitior	-	0.9307	93.07%
P-glycoprotein substrate	-	0.9773	97.73%
CYP3A4 substrate	-	0.5693	56.93%
CYP2C9 substrate	+	0.5858	58.58%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.8022	80.22%
CYP2C9 inhibition	-	0.9322	93.22%
CYP2C19 inhibition	-	0.6962	69.62%
CYP2D6 inhibition	-	0.9305	93.05%
CYP1A2 inhibition	+	0.6735	67.35%
CYP2C8 inhibition	-	0.9089	90.89%
CYP inhibitory promiscuity	-	0.8959	89.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5629	56.29%
Eye corrosion	-	0.8249	82.49%
Eye irritation	+	0.6916	69.16%
Skin irritation	-	0.5166	51.66%
Skin corrosion	-	0.9608	96.08%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5214	52.14%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6370	63.70%
skin sensitisation	+	0.5739	57.39%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6978	69.78%
Acute Oral Toxicity (c)	III	0.6828	68.28%
Estrogen receptor binding	-	0.8723	87.23%
Androgen receptor binding	-	0.7321	73.21%
Thyroid receptor binding	-	0.7730	77.30%
Glucocorticoid receptor binding	-	0.7242	72.42%
Aromatase binding	-	0.7803	78.03%
PPAR gamma	-	0.5603	56.03%
Honey bee toxicity	-	0.8103	81.03%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9497	94.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.28%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.34%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.20%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.16%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.27%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.30%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	82.29%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.51%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.83%	96.09%

Plants that contains it

• Arctium lappa
• Aristolochia mollissima

Cross-Links

• PubChem: 5315198
• NPASS: NPC88456
• LOTUS: LTS0025740
• wikiData: Q105132481