(3R,4R,5S)-3-hexadec-15-en-7,9-diynyl-4-hydroxy-5-methyloxolan-2-one

Details

• Internal ID: fa3a5030-c246-444b-aac3-a8a07cc7d0bd
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3R,4R,5S)-3-hexadec-15-en-7,9-diynyl-4-hydroxy-5-methyloxolan-2-one
• SMILES (Canonical): CC1C(C(C(=O)O1)CCCCCCC#CC#CCCCCC=C)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H](C(=O)O1)CCCCCCC#CC#CCCCCC=C)O
• InChI: InChI=1S/C21H30O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-20(22)18(2)24-21(19)23/h3,18-20,22H,1,4-7,12-17H2,2H3/t18-,19+,20-/m0/s1
• InChI Key: ZKQDJNRSBPEBRO-ZCNNSNEGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.21949481 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.00
• 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	+	0.9419	94.19%
Caco-2	-	0.6429	64.29%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7112	71.12%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8575	85.75%
OATP1B3 inhibitior	+	0.9397	93.97%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.5264	52.64%
P-glycoprotein inhibitior	-	0.7151	71.51%
P-glycoprotein substrate	-	0.7911	79.11%
CYP3A4 substrate	+	0.5598	55.98%
CYP2C9 substrate	-	0.8028	80.28%
CYP2D6 substrate	-	0.8600	86.00%
CYP3A4 inhibition	-	0.7004	70.04%
CYP2C9 inhibition	-	0.8042	80.42%
CYP2C19 inhibition	-	0.6448	64.48%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.6958	69.58%
CYP2C8 inhibition	-	0.8237	82.37%
CYP inhibitory promiscuity	-	0.8173	81.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8728	87.28%
Carcinogenicity (trinary)	Non-required	0.5697	56.97%
Eye corrosion	-	0.8406	84.06%
Eye irritation	-	0.8743	87.43%
Skin irritation	-	0.5385	53.85%
Skin corrosion	-	0.8091	80.91%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4245	42.45%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7333	73.33%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.6362	63.62%
Acute Oral Toxicity (c)	III	0.6220	62.20%
Estrogen receptor binding	+	0.6276	62.76%
Androgen receptor binding	+	0.6242	62.42%
Thyroid receptor binding	+	0.5884	58.84%
Glucocorticoid receptor binding	+	0.5825	58.25%
Aromatase binding	-	0.6684	66.84%
PPAR gamma	+	0.6138	61.38%
Honey bee toxicity	-	0.8017	80.17%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6062	60.62%
Fish aquatic toxicity	+	0.9503	95.03%

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	91.38%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.01%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.72%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.89%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.85%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.14%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.45%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.01%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.62%	94.80%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.45%	96.00%

Plants that contains it

• Meiogyne cylindrocarpa

Cross-Links

• PubChem: 162941825
• LOTUS: LTS0226904
• wikiData: Q105378656