Gamma-undecalactone

Details

• Internal ID: e0e5c2f7-a053-49cb-892e-db8648ea2947
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: 5-heptyloxolan-2-one
• InChI: InChI=1S/C11H20O2/c1-2-3-4-5-6-7-10-8-9-11(12)13-10/h10H,2-9H2,1H3
• InChI Key: PHXATPHONSXBIL-UHFFFAOYSA-N
• Popularity: 90 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.27 g/mol
• Exact Mass: 184.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.05
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 104-67-6
• 2(3H)-Furanone, 5-heptyldihydro-
• Undecan-4-olide
• Peach aldehyde
• 5-heptyloxolan-2-one
• Persicol
• 1,4-Undecanolide
• Peach lactone
• 5-Heptyldihydro-2(3H)-furanone
• Aldehyde C-14 peach
• gamma-Undecanolactone
• gamma-Undecanolide
• 1,4-Hendecanolide
• 4-Hydroxyundecanoic acid lactone
• .gamma.-Undecalactone
• FEMA No. 3091
• gamma-Undekalakton
• gamma-Heptyl-gamma-butyrolactone
• gamma-n-Heptylbutyrolactone
• gamma-Undekalakton [Czech]
• gamma-Undecalactone (natural)
• CCRIS 1425
• NSC 406421
• QB1T0AG2YL
• EINECS 203-225-4
• BRN 0081943
• DTXSID4034287
• AI3-00751
• Undecanoic acid, 4-hydroxy-, gamma-lactone
• 5-Heptyl-dihydrofuran-2(3H)-one
• GAMMA UNDECALACTONE
• NSC-46118
• NSC-76413
• NSC-406421
• DTXCID2014287
• PHXATPHONSXBIL-UHFFFAOYSA-
• GAMMA-UNDECALACTONE [FCC]
• Undecanoic acid, 4-hydroxy-, .gamma.-lactone
• EC 203-225-4
• (RS)-.GAMMA.-UNDECALACTONE
• .GAMMA.-UNDECALACTONE [FHFI]
• 4Undecanolide
• Undecan4olide
• gammaUndecanolide
• gammaUndekalakton
• deltaundecalactone
• gammaundecalactone
• 1,4undecanolide
• 1,4Hendecanolide
• gammaUndecanolactone
• Aldehyde C14 peach
• Aldehyde C-14 pure
• gammanHeptylbutyrolactone
• RefChem:639609
• gammaHeptylgammabutyrolactone
• gammaUndecalactone (natural)
• 5Heptyldihydro2(3H)furanone
• 4Hydroxyundecanoic acid lactone
• (RS)-GAMMA-UNDECALACTONE
• (+-)-GAMMA-UNDECALACTONE
• GAMMA-UNDECALACTONE [INCI]
• (+-)-.GAMMA.-UNDECALACTONE
• Undecanoic acid, 4hydroxy, gammalactone
• 203-225-4
• InChI=1/C11H20O2/c1-2-3-4-5-6-7-10-8-9-11(12)13-10/h10H,2-9H2,1H3
• 4-Undecanolide
• 5-Heptyldihydrofuran-2(3H)-one
• Undecanoic gamma-lactone
• MFCD00005405
• g-Undecalactone
• 57084-17-0
• Aldehyde C14
• .gamma.-n-Heptylbutyrolactone
• 5-Heptyl-dihydro-furan-2-one
• .gamma.-Undecalatone
• .gamma.-Undecanolide
• xi-gamma-Undecalactone
• .gamma.-Undecanolactone
• .gamma.-Heptylbutyrolactone
• CHEMBL195827
• CHEBI:89362
• .gamma.-Heptyl-.gamma.-butyrolactone
• 4-Hydroxyundecanoic acid, .gamma.-lactone
• WLN: T5OVTJ E7
• Undecanoic acid, .gamma.-lactone
• UNII-QB1T0AG2YL
• 5-heptyltetrahydrofuran-2-one
• Dihydro-5-heptyl-2(3H)-furanone
• |A-Undecanolactone
• Undecanolide-1,4
• .gamma.-Undekalakton
• undecylene methyl lactone
• Undecanoic gamma -lactone
• UNDECALACTONE GAMMA
• Undecanoic .gamma.-lactone
• SCHEMBL113498
• orb1297004
• Undecanoic gamma-lactone, 99%
• 4- hydroxyundecanoic acid lactone
• HMS1786B22
• NSC46118
• NSC76413
• 5-Heptyldihydro-2(3H)-furanone #
• Tox21_300063
• BDBM50168011
• LMFA07040030
• MSK010001
• NSC406421
• 5-heptyl-3,4,5-trihydrofuran-2-one
• AKOS001076126
• (+/-)-.GAMMA.-UNDECALACTONE
• CS-W016994
• FU03388
• HY-W016278
• gamma-Undecalactone, analytical standard
• gamma-Undecalactone, >=98%, FCC, FG
• NCGC00164025-01
• NCGC00164025-02
• NCGC00254148-01
• BS-14211
• CAS-104-67-6
• SY011229
• DB-040554
• NS00076562
• ST50826887
• U0003
• EN300-05986
• D70490
• gamma-Undecalactone, natural (US), >=98%, FG
• F240934
• Q24734376
• Z90120148
• gammaundecalactone;(+/-)-4-Undecanolide;Undecanoic ?-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.8030	80.30%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Plasma membrane	0.4605	46.05%
OATP2B1 inhibitior	-	0.8450	84.50%
OATP1B1 inhibitior	+	0.9280	92.80%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7896	78.96%
P-glycoprotein inhibitior	-	0.9656	96.56%
P-glycoprotein substrate	-	0.9127	91.27%
CYP3A4 substrate	-	0.5958	59.58%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8634	86.34%
CYP3A4 inhibition	-	0.9096	90.96%
CYP2C9 inhibition	-	0.8493	84.93%
CYP2C19 inhibition	-	0.6249	62.49%
CYP2D6 inhibition	-	0.9364	93.64%
CYP1A2 inhibition	-	0.6255	62.55%
CYP2C8 inhibition	-	0.9182	91.82%
CYP inhibitory promiscuity	-	0.9030	90.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6560	65.60%
Eye corrosion	+	0.6594	65.94%
Eye irritation	+	0.9711	97.11%
Skin irritation	+	0.8099	80.99%
Skin corrosion	-	0.8543	85.43%
Ames mutagenesis	-	0.9152	91.52%
Human Ether-a-go-go-Related Gene inhibition	-	0.4913	49.13%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.5701	57.01%
skin sensitisation	-	0.5935	59.35%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	-	0.8542	85.42%
Mitochondrial toxicity	-	0.9250	92.50%
Nephrotoxicity	+	0.5224	52.24%
Acute Oral Toxicity (c)	III	0.6100	61.00%
Estrogen receptor binding	-	0.9034	90.34%
Androgen receptor binding	-	0.8511	85.11%
Thyroid receptor binding	-	0.8488	84.88%
Glucocorticoid receptor binding	-	0.7393	73.93%
Aromatase binding	-	0.8708	87.08%
PPAR gamma	-	0.6281	62.81%
Honey bee toxicity	-	0.9885	98.85%
Biodegradation	+	0.7250	72.50%
Crustacea aquatic toxicity	+	0.7904	79.04%
Fish aquatic toxicity	+	0.8534	85.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	45000 nM	IC50	PMID: 15916432

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.02%	98.95%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	91.53%	90.24%
CHEMBL230	P35354	Cyclooxygenase-2	90.16%	89.63%
CHEMBL2996	Q05655	Protein kinase C delta	89.55%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.88%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.33%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.72%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.47%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.27%	99.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.15%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.54%	92.50%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.52%	91.81%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.03%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.82%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.07%	100.00%

Plants that contains it

• Bupleurum chinense
• Gossypium hirsutum
• Prunus persica

Cross-Links

• PubChem: 7714
• NPASS: NPC145045
• ChEMBL: CHEMBL195827
• LOTUS: LTS0052382
• wikiData: Q24734376