(3R,5S)-3-[(7E)-hexadeca-7,15-dien-9,11-diynyl]-5-(hydroxymethyl)oxolan-2-one

Details

• Internal ID: 7fb1a499-2506-4900-9f45-59aa4e79491b
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3R,5S)-3-[(7E)-hexadeca-7,15-dien-9,11-diynyl]-5-(hydroxymethyl)oxolan-2-one
• SMILES (Canonical): C=CCCC#CC#CC=CCCCCCCC1CC(OC1=O)CO
• SMILES (Isomeric): C=CCCC#CC#C/C=C/CCCCCC[C@@H]1C[C@H](OC1=O)CO
• InChI: InChI=1S/C21H28O3/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/h2,9-10,19-20,22H,1,3-4,11-18H2/b10-9+/t19-,20+/m1/s1
• InChI Key: VKRYMBMEZLTVEX-FBWYZNFGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.20384475 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 3.78
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 10

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	-	0.7531	75.31%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7679	76.79%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.8815	88.15%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.5909	59.09%
P-glycoprotein inhibitior	-	0.6505	65.05%
P-glycoprotein substrate	-	0.6766	67.66%
CYP3A4 substrate	+	0.5969	59.69%
CYP2C9 substrate	-	0.8185	81.85%
CYP2D6 substrate	-	0.8567	85.67%
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	-	0.6510	65.10%
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	-	0.8884	88.84%
Skin irritation	-	0.7026	70.26%
Skin corrosion	-	0.7317	73.17%
Ames mutagenesis	-	0.6407	64.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.7946	79.46%
Micronuclear	-	0.9141	91.41%
Hepatotoxicity	-	0.5698	56.98%
skin sensitisation	-	0.7941	79.41%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.7300	73.00%
Acute Oral Toxicity (c)	III	0.5948	59.48%
Estrogen receptor binding	+	0.7204	72.04%
Androgen receptor binding	+	0.5758	57.58%
Thyroid receptor binding	+	0.5427	54.27%
Glucocorticoid receptor binding	+	0.6110	61.10%
Aromatase binding	-	0.5472	54.72%
PPAR gamma	+	0.5384	53.84%
Honey bee toxicity	-	0.7442	74.42%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5288	52.88%
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	95.04%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.32%	99.17%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	90.29%	92.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.24%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.12%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.53%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.84%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	84.53%	89.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.24%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.89%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.74%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.41%	95.89%

Plants that contains it

• Mitrephora glabra

Cross-Links

• PubChem: 44606076
• LOTUS: LTS0027803
• wikiData: Q105288042