Ircinolin A

Details

• Internal ID: b2163ade-2663-43c9-9396-ea9c35e75a0e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (5S)-5-methyl-5-[(1R,4E,6S,8E)-1,6,14-trihydroxy-4,8-dimethyl-13-oxotetradeca-4,8-dienyl]oxolan-2-one
• InChI: InChI=1S/C21H34O6/c1-15(6-4-5-7-17(23)14-22)12-18(24)13-16(2)8-9-19(25)21(3)11-10-20(26)27-21/h6,13,18-19,22,24-25H,4-5,7-12,14H2,1-3H3/b15-6+,16-13+/t18-,19+,21-/m0/s1
• InChI Key: YKUZFPGHZVFVLY-DZMSUEBXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₆
• Molecular Weight: 382.50 g/mol
• Exact Mass: 382.23553880 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 12

Synonyms

• RefChem:148698
• (5S)-5-methyl-5-((1R,4E,6S,8E)-1,6,14-trihydroxy-4,8-dimethyl-13-oxotetradeca-4,8-dienyl)oxolan-2-one
• CHEMBL1823119
• CHEBI:69461
• Q27137799

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9486	94.86%
Caco-2	-	0.5264	52.64%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7624	76.24%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.8483	84.83%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5280	52.80%
BSEP inhibitior	+	0.8305	83.05%
P-glycoprotein inhibitior	-	0.6658	66.58%
P-glycoprotein substrate	-	0.5773	57.73%
CYP3A4 substrate	+	0.6529	65.29%
CYP2C9 substrate	-	0.8093	80.93%
CYP2D6 substrate	-	0.8554	85.54%
CYP3A4 inhibition	-	0.6062	60.62%
CYP2C9 inhibition	-	0.8306	83.06%
CYP2C19 inhibition	-	0.8620	86.20%
CYP2D6 inhibition	-	0.9186	91.86%
CYP1A2 inhibition	-	0.8332	83.32%
CYP2C8 inhibition	-	0.7593	75.93%
CYP inhibitory promiscuity	-	0.9473	94.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9528	95.28%
Carcinogenicity (trinary)	Non-required	0.6201	62.01%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9006	90.06%
Skin irritation	-	0.5482	54.82%
Skin corrosion	-	0.9546	95.46%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4125	41.25%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6601	66.01%
skin sensitisation	-	0.8698	86.98%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6394	63.94%
Acute Oral Toxicity (c)	III	0.5967	59.67%
Estrogen receptor binding	+	0.5533	55.33%
Androgen receptor binding	-	0.5796	57.96%
Thyroid receptor binding	+	0.6211	62.11%
Glucocorticoid receptor binding	+	0.6445	64.45%
Aromatase binding	-	0.4834	48.34%
PPAR gamma	+	0.5294	52.94%
Honey bee toxicity	-	0.8101	81.01%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9004	90.04%

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	98.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.36%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.90%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.94%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.63%	99.17%
CHEMBL299	P17252	Protein kinase C alpha	90.26%	98.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.30%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	84.10%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.05%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.95%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.81%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.07%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54672087
• LOTUS: LTS0265967
• wikiData: Q27137799