Curcumenolactone C

Details

• Internal ID: 93228beb-6efb-4d49-a315-09fa1bb74fa6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (4aR,5R,5aS,6aR)-6a-hydroxy-3,5a-dimethyl-5-(3-oxobutyl)-3,4a,5,6-tetrahydrocyclopropa[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2=CC3C(C3(CC2(OC1=O)O)C)CCC(=O)C
• SMILES (Isomeric): CC1C2=C[C@@H]3[C@H]([C@@]3(C[C@]2(OC1=O)O)C)CCC(=O)C
• InChI: InChI=1S/C15H20O4/c1-8(16)4-5-10-12-6-11-9(2)13(17)19-15(11,18)7-14(10,12)3/h6,9-10,12,18H,4-5,7H2,1-3H3/t9?,10-,12-,14+,15-/m1/s1
• InChI Key: LKCVEORRYWUEAO-YRVVTGAMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.5492	54.92%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6715	67.15%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9170	91.70%
OATP1B3 inhibitior	+	0.9670	96.70%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.5521	55.21%
BSEP inhibitior	-	0.8073	80.73%
P-glycoprotein inhibitior	-	0.8587	85.87%
P-glycoprotein substrate	-	0.7459	74.59%
CYP3A4 substrate	+	0.5662	56.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8591	85.91%
CYP3A4 inhibition	-	0.6366	63.66%
CYP2C9 inhibition	-	0.8341	83.41%
CYP2C19 inhibition	-	0.9268	92.68%
CYP2D6 inhibition	-	0.9596	95.96%
CYP1A2 inhibition	-	0.5936	59.36%
CYP2C8 inhibition	-	0.8935	89.35%
CYP inhibitory promiscuity	-	0.9519	95.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5555	55.55%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9026	90.26%
Skin irritation	+	0.6322	63.22%
Skin corrosion	-	0.8862	88.62%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5517	55.17%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5631	56.31%
skin sensitisation	-	0.7867	78.67%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5591	55.91%
Acute Oral Toxicity (c)	III	0.4104	41.04%
Estrogen receptor binding	+	0.5281	52.81%
Androgen receptor binding	+	0.6009	60.09%
Thyroid receptor binding	+	0.6809	68.09%
Glucocorticoid receptor binding	+	0.7408	74.08%
Aromatase binding	-	0.7652	76.52%
PPAR gamma	-	0.5585	55.85%
Honey bee toxicity	-	0.9053	90.53%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9861	98.61%

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	96.79%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.44%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.59%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.99%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.26%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.02%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.23%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.04%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.88%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.17%	100.00%

Plants that contains it

• Curcuma zedoaria

Cross-Links

• PubChem: 101110756
• NPASS: NPC307414
• LOTUS: LTS0210021
• wikiData: Q105152989