Oropheolide

Details

• Internal ID: 9e50d185-ec8f-4b1e-8816-301901adbfa4
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3R,5S)-3-hexadec-15-en-7,9,11-triynyl-5-(hydroxymethyl)oxolan-2-one
• SMILES (Canonical): C=CCCC#CC#CC#CCCCCCCC1CC(OC1=O)CO
• SMILES (Isomeric): C=CCCC#CC#CC#CCCCCCC[C@@H]1C[C@H](OC1=O)CO
• InChI: InChI=1S/C21H26O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-17-20(18-22)24-21(19)23/h2,19-20,22H,1,3-4,11-18H2/t19-,20+/m1/s1
• InChI Key: PNMPARWIIBHFCP-UXHICEINSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₃
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.18819469 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• CHEMBL1080662

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9753	97.53%
Caco-2	-	0.7775	77.75%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7679	76.79%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.9072	90.72%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6657	66.57%
P-glycoprotein inhibitior	-	0.7674	76.74%
P-glycoprotein substrate	-	0.7689	76.89%
CYP3A4 substrate	+	0.5506	55.06%
CYP2C9 substrate	-	0.5966	59.66%
CYP2D6 substrate	-	0.8445	84.45%
CYP3A4 inhibition	-	0.8375	83.75%
CYP2C9 inhibition	-	0.8892	88.92%
CYP2C19 inhibition	-	0.7906	79.06%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.7932	79.32%
CYP2C8 inhibition	-	0.7364	73.64%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.7062	70.62%
Eye corrosion	-	0.7743	77.43%
Eye irritation	-	0.8144	81.44%
Skin irritation	-	0.7026	70.26%
Skin corrosion	-	0.7317	73.17%
Ames mutagenesis	-	0.7207	72.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.3637	36.37%
Micronuclear	-	0.9141	91.41%
Hepatotoxicity	+	0.5427	54.27%
skin sensitisation	-	0.7941	79.41%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.8090	80.90%
Acute Oral Toxicity (c)	III	0.5948	59.48%
Estrogen receptor binding	+	0.5631	56.31%
Androgen receptor binding	+	0.5326	53.26%
Thyroid receptor binding	+	0.5784	57.84%
Glucocorticoid receptor binding	+	0.5515	55.15%
Aromatase binding	-	0.5359	53.59%
PPAR gamma	-	0.5516	55.16%
Honey bee toxicity	-	0.7580	75.80%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5012	50.12%
Fish aquatic toxicity	+	0.7667	76.67%

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	95.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.91%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.79%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.77%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	87.12%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.51%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.44%	94.45%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	85.24%	92.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.98%	95.56%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.76%	95.58%
CHEMBL1871	P10275	Androgen Receptor	81.21%	96.43%
CHEMBL2996	Q05655	Protein kinase C delta	80.05%	97.79%

Plants that contains it

• Mitrephora glabra

Cross-Links

• PubChem: 44606075
• LOTUS: LTS0190324
• wikiData: Q105212048