(3R,5S)-5-(hydroxymethyl)-3-icos-19-en-11-ynyloxolan-2-one

Details

• Internal ID: 18448a48-a16e-46ba-ac6d-45e0f3744474
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3R,5S)-5-(hydroxymethyl)-3-icos-19-en-11-ynyloxolan-2-one
• SMILES (Canonical): C=CCCCCCCC#CCCCCCCCCCCC1CC(OC1=O)CO
• SMILES (Isomeric): C=CCCCCCCC#CCCCCCCCCCC[C@@H]1C[C@H](OC1=O)CO
• InChI: InChI=1S/C25H42O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23-21-24(22-26)28-25(23)27/h2,23-24,26H,1,3-8,11-22H2/t23-,24+/m1/s1
• InChI Key: PDSBIIGAXPWHRT-RPWUZVMVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₂O₃
• Molecular Weight: 390.60 g/mol
• Exact Mass: 390.31339520 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 8.50
• Atomic LogP (AlogP): 6.34
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9753	97.53%
Caco-2	-	0.8330	83.30%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7679	76.79%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9273	92.73%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6647	66.47%
P-glycoprotein inhibitior	-	0.6724	67.24%
P-glycoprotein substrate	-	0.8370	83.70%
CYP3A4 substrate	+	0.5168	51.68%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.8467	84.67%
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	-	0.7937	79.37%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.7062	70.62%
Eye corrosion	-	0.7743	77.43%
Eye irritation	-	0.6362	63.62%
Skin irritation	-	0.7026	70.26%
Skin corrosion	-	0.7317	73.17%
Ames mutagenesis	-	0.7407	74.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.6507	65.07%
Micronuclear	-	0.9141	91.41%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.7941	79.41%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.7534	75.34%
Acute Oral Toxicity (c)	III	0.5948	59.48%
Estrogen receptor binding	+	0.7131	71.31%
Androgen receptor binding	-	0.5205	52.05%
Thyroid receptor binding	-	0.4871	48.71%
Glucocorticoid receptor binding	+	0.6261	62.61%
Aromatase binding	-	0.5984	59.84%
PPAR gamma	+	0.5245	52.45%
Honey bee toxicity	-	0.7870	78.70%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5112	51.12%
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	97.07%	91.11%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	93.36%	92.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.90%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	88.94%	89.63%
CHEMBL325	Q13547	Histone deacetylase 1	88.72%	95.92%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.81%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.81%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.81%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	85.16%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.90%	89.00%
CHEMBL1829	O15379	Histone deacetylase 3	84.54%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.37%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.58%	93.99%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.31%	92.88%

Plants that contains it

• Goniothalamus gardneri

Cross-Links

• PubChem: 9977730
• LOTUS: LTS0234360
• wikiData: Q105206719