cis-3-Methyl-4-octanolide

Details

• Internal ID: 51b21a17-514e-46f6-8fce-3f62c8998878
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (4R,5R)-5-butyl-4-methyloxolan-2-one
• SMILES (Canonical): CCCCC1C(CC(=O)O1)C
• SMILES (Isomeric): CCCC[C@@H]1[C@@H](CC(=O)O1)C
• InChI: InChI=1S/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3/t7-,8-/m1/s1
• InChI Key: WNVCMFHPRIBNCW-HTQZYQBOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22 g/mol
• Exact Mass: 156.115029749 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• cis-Whiskey lactone
• cis-Oaklactone
• cis-Methyloctanolide
• Whiskey lactone, (Z)-
• (Z)-Oak lactone
• (+/-)-cis-Whiskey lactone
• (4R,5R)-5-butyl-4-methyloxolan-2-one
• 55013-32-6
• FEMA No. 3803, Z-
• beta-Methyl-gamma-octalactone, cis-
• 105015-53-0
• 5-Butyl-4-methyldihydro-2(3H)-furanone, (Z)-
• 2(3H)-Furanone, 5-butyldihydro-4-methyl-, cis-
• O93PZ85MTG
• 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5R)-
• 5-Butyl-4-methyldihydrofuran-2(3H)-one, (Z)-
• 5-BUTYLDIHYDRO-4-METHYL-2(3H)-FURANONE (CIS)
• 9678LTP737
• cis-.beta.-Methyl-.gamma.-Octalactone
• 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5R)-rel-
• (Z)-Oaklactone
• (cis)-Oak-lactone
• UNII-O93PZ85MTG
• (.+/-.)-cis-Whiskey lactone
• (+-)-cis-Whiskey lactone
• UNII-9678LTP737
• cis-beta-Methyl-gamma-Octalactone
• cis-4-methyl-5-butyldihydro-2(3H)-furanone
• cis-5-Butyl-4-methyldihydrofuran-2(3H)-one
• FEMA No. 3803, cis-(+-)-
• cis-3-Methyl-4-octanolid
• 5-Butyl-4-methyldihydro-2(3H)-furanone, cis-(+-)-
• SCHEMBL9171097
• (+)-CIS-WHISKEY LACTONE
• CHEBI:171765
• WNVCMFHPRIBNCW-HTQZYQBOSA-N
• DTXSID801009384
• cis-(+)-5-Butyl-4-methyldihydro-2(3H)-furanone
• Q5122105
• (4R,5R)-5-BUTYLDIHYDRO-4-METHYL-2(3H)-FURANONE
• 5-BUTYL-4-METHYLDIHYDRO-2(3H)-FURANONE, CIS-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.8473	84.73%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5004	50.04%
OATP2B1 inhibitior	-	0.8446	84.46%
OATP1B1 inhibitior	+	0.9268	92.68%
OATP1B3 inhibitior	+	0.9474	94.74%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9583	95.83%
P-glycoprotein inhibitior	-	0.9710	97.10%
P-glycoprotein substrate	-	0.8960	89.60%
CYP3A4 substrate	-	0.6402	64.02%
CYP2C9 substrate	+	0.6168	61.68%
CYP2D6 substrate	-	0.8637	86.37%
CYP3A4 inhibition	-	0.8164	81.64%
CYP2C9 inhibition	-	0.8952	89.52%
CYP2C19 inhibition	-	0.7288	72.88%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.6792	67.92%
CYP2C8 inhibition	-	0.9550	95.50%
CYP inhibitory promiscuity	-	0.8907	89.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6911	69.11%
Eye corrosion	-	0.6956	69.56%
Eye irritation	+	0.8648	86.48%
Skin irritation	+	0.6557	65.57%
Skin corrosion	-	0.9001	90.01%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6984	69.84%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	+	0.4773	47.73%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	-	0.8444	84.44%
Mitochondrial toxicity	-	0.9250	92.50%
Nephrotoxicity	+	0.6432	64.32%
Acute Oral Toxicity (c)	III	0.7189	71.89%
Estrogen receptor binding	-	0.9500	95.00%
Androgen receptor binding	-	0.7910	79.10%
Thyroid receptor binding	-	0.8379	83.79%
Glucocorticoid receptor binding	-	0.9174	91.74%
Aromatase binding	-	0.8359	83.59%
PPAR gamma	-	0.9080	90.80%
Honey bee toxicity	-	0.9645	96.45%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9249	92.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.62%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.72%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.74%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.01%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	83.55%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.55%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.38%	94.80%
CHEMBL299	P17252	Protein kinase C alpha	81.68%	98.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.33%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.23%	93.56%

Plants that contains it

• Quercus serrata

Cross-Links

• PubChem: 41285
• LOTUS: LTS0101258
• wikiData: Q5122105