Aspergillide A

Details

• Internal ID: fccfcd47-64a2-4919-95d0-2eba73236ad6
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,5S,9E,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
• SMILES (Canonical): CC1CCCC=CC2CCC(C(O2)CC(=O)O1)O
• SMILES (Isomeric): C[C@H]1CCC/C=C/[C@H]2CC[C@@H]([C@H](O2)CC(=O)O1)O
• InChI: InChI=1S/C14H22O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6,10-13,15H,2-3,5,7-9H2,1H3/b6-4+/t10-,11-,12-,13+/m0/s1
• InChI Key: FDJDTDDUDZAAFP-GDHSIMSHSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.32 g/mol
• Exact Mass: 254.15180918 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.96
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEBI:65450
• (1R,5S,9E,11R,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
• CHEMBL2407403
• Q27133894

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9796	97.96%
Caco-2	-	0.5559	55.59%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5546	55.46%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.8768	87.68%
OATP1B3 inhibitior	+	0.9242	92.42%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7404	74.04%
P-glycoprotein inhibitior	-	0.9429	94.29%
P-glycoprotein substrate	-	0.8705	87.05%
CYP3A4 substrate	+	0.5151	51.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8591	85.91%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9764	97.64%
CYP2C19 inhibition	-	0.9255	92.55%
CYP2D6 inhibition	-	0.9579	95.79%
CYP1A2 inhibition	-	0.6364	63.64%
CYP2C8 inhibition	-	0.9294	92.94%
CYP inhibitory promiscuity	-	0.9928	99.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6590	65.90%
Eye corrosion	-	0.9462	94.62%
Eye irritation	-	0.9739	97.39%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7688	76.88%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5430	54.30%
skin sensitisation	-	0.8159	81.59%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.7536	75.36%
Acute Oral Toxicity (c)	III	0.4880	48.80%
Estrogen receptor binding	-	0.5095	50.95%
Androgen receptor binding	-	0.7347	73.47%
Thyroid receptor binding	-	0.5577	55.77%
Glucocorticoid receptor binding	+	0.6626	66.26%
Aromatase binding	-	0.8552	85.52%
PPAR gamma	-	0.6007	60.07%
Honey bee toxicity	-	0.9179	91.79%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.7788	77.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.24%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.92%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.27%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.75%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.13%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.10%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.64%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.51%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.05%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 70678632
• LOTUS: LTS0156340
• wikiData: Q27133894