gamma-Octalactone

Details

• Internal ID: 3b7a0d9a-1e82-4cab-b82e-d25314bc337d
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: 5-butyloxolan-2-one
• SMILES (Canonical): CCCCC1CCC(=O)O1
• SMILES (Isomeric): CCCCC1CCC(=O)O1
• InChI: InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
• InChI Key: IPBFYZQJXZJBFQ-UHFFFAOYSA-N
• Popularity: 114 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.20 g/mol
• Exact Mass: 142.099379685 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 104-50-7
• 4-Octanolide
• 5-butyloxolan-2-one
• 2(3H)-Furanone, 5-butyldihydro-
• 4-Hydroxyoctanoic acid lactone
• 8-Oxo-5-octanolide
• 5-Butyldihydro-2(3H)-furanone
• Octanoic acid, gamma lactone
• gamma-Butyl-gamma-butyrolactone
• gamma-N-Butyl-gamma-butyrolactone
• FEMA No. 2796
• UHD6M52X0K
• DTXSID1047609
• NSC-24270
• NSC-26509
• DTXCID9027609
• CHEBI:145738
• RefChem:639598
• 203-208-1
• gamma-Octanoic lactone
• 5-Butyldihydrofuran-2(3H)-one
• Octan-4-olide
• gamma-Octanolactone
• Octanolide-1,4
• 4-Butyl-gamma-butyrolactone
• 5-Butyltetrahydro-2-furanone
• .gamma.-Octalactone
• Octano-1,4-lactone
• 2(3H)-Furanone, dihydro-5-butyl-
• 4-Butyl-4-hydroxybutyric acid lactone
• g-Octalactone
• gamma-octanolide
• MFCD00005402
• NSC 24270
• .gamma.-Octanolactone
• Octanoic acid, 4-hydroxy-, lactone
• .gamma.-Butyl-.gamma.-butyrolactone
• .gamma.-Butylbutyrolactone
• 4-Butyl-.gamma.-butyrolactone
• Octanoic acid, .gamma. lactone
• 5-Butyl-dihydrofuran-2(3H)-one
• .gamma.-N-Butyl-.gamma.-butyrolactone
• 4-Hydroxyoctanoic acid, .gamma.-lactone
• Octanoic acid, 4-hydroxy-, .gamma.-lactone
• WLN: T5OVTJ E4
• Octanoic acid, .gamma.-lactone
• Gamma Octalactone
• gamma-Octalactone (natural)
• 5-butyltetrahydrofuran-2-one
• EINECS 203-208-1
• UNII-UHD6M52X0K
• BRN 0111677
• AI3-35896
• .gamma. -0ctalactone
• gamma-Butylbutyrolactone
• gamma -Octanoic lactone
• 5-17-09-00073 (Beilstein Handbook Reference)
• gamma-Octanoic lactone, 97%
• SCHEMBL111822
• 5-Butylhydro-2(3H)-furanone
• SCHEMBL9617846
• GAMMA-OCTALACTONE [FCC]
• 5-butyl-tetrahydro-furan-2-one
• CHEMBL3559967
• FEMA 2796
• IPBFYZQJXZJBFQ-UHFFFAOYSA-
• (RS)-.GAMMA.-OCTALACTONE
• dihydro-5-butyl-2(3H)-furanone
• .GAMMA.-OCTALACTONE [FHFI]
• 5-Butyldihydro-2(3H)-furanone #
• NSC24270
• NSC26509
• Tox21_302569
• AC2057
• LMFA07040016
• MSK014021
• 5-butyl-3,4,5-trihydrofuran-2-one
• gamma-Octalactone, analytical standard
• AKOS015904720
• CS-W018278
• FO03392
• MSK014021-100B
• gamma-Octalactone, >=97%, FCC, FG
• NCGC00256744-01
• BS-14348
• CAS-104-50-7
• gamma-Octalactone, natural, >=97%, FG
• SY015123
• H0232
• NS00013082
• ST50823795
• EN300-253946
• gamma-Octalactone Solution in Acetone, 100ug/mL
• Q27291078
• InChI=1/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8055	80.55%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Plasma membrane	0.5012	50.12%
OATP2B1 inhibitior	-	0.8425	84.25%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9449	94.49%
P-glycoprotein inhibitior	-	0.9849	98.49%
P-glycoprotein substrate	-	0.9381	93.81%
CYP3A4 substrate	-	0.6309	63.09%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8634	86.34%
CYP3A4 inhibition	-	0.9363	93.63%
CYP2C9 inhibition	-	0.8382	83.82%
CYP2C19 inhibition	-	0.6159	61.59%
CYP2D6 inhibition	-	0.9434	94.34%
CYP1A2 inhibition	-	0.6366	63.66%
CYP2C8 inhibition	-	0.9395	93.95%
CYP inhibitory promiscuity	-	0.9058	90.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6541	65.41%
Eye corrosion	+	0.7454	74.54%
Eye irritation	+	0.9690	96.90%
Skin irritation	+	0.7308	73.08%
Skin corrosion	-	0.8572	85.72%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7002	70.02%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.5906	59.06%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	-	0.7986	79.86%
Mitochondrial toxicity	-	0.9250	92.50%
Nephrotoxicity	+	0.5385	53.85%
Acute Oral Toxicity (c)	III	0.8612	86.12%
Estrogen receptor binding	-	0.9455	94.55%
Androgen receptor binding	-	0.8742	87.42%
Thyroid receptor binding	-	0.8629	86.29%
Glucocorticoid receptor binding	-	0.9011	90.11%
Aromatase binding	-	0.8515	85.15%
PPAR gamma	-	0.8457	84.57%
Honey bee toxicity	-	0.9897	98.97%
Biodegradation	+	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5448	54.48%
Fish aquatic toxicity	+	0.8247	82.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.76%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.75%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.33%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.69%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.96%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	82.90%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.84%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.42%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.30%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.07%	100.00%

Plants that contains it

• Akebia quinata
• Akebia trifoliata
• Aspalathus linearis
• Bupleurum chinense
• Carica papaya
• Glycyrrhiza glabra
• Mangifera indica
• Polygala senega
• Prunus armeniaca
• Thymus martinezii

Cross-Links

• PubChem: 7704
• NPASS: NPC273545
• LOTUS: LTS0055875
• wikiData: Q27291078