Linderalactone

Details

• Internal ID: fbb2a2f2-2cf4-446d-9756-ea580572ce4c
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (1R,8E)-3,8-dimethyl-5,14-dioxatricyclo[10.2.1.02,6]pentadeca-2(6),3,8,12(15)-tetraen-13-one
• SMILES (Canonical): CC1=CCCC2=CC(C3=C(C1)OC=C3C)OC2=O
• SMILES (Isomeric): C/C/1=C\CCC2=C[C@H](C3=C(C1)OC=C3C)OC2=O
• InChI: InChI=1S/C15H16O3/c1-9-4-3-5-11-7-13(18-15(11)16)14-10(2)8-17-12(14)6-9/h4,7-8,13H,3,5-6H2,1-2H3/b9-4+/t13-/m1/s1
• InChI Key: LWCKQMHMTSRRAA-QGQQYVBWSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 39.40 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.39
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 728-61-0
• (R,7Z,10E)-3,11-dimethyl-4,8,9,12-tetrahydro-6H-4,7-(metheno)furo[3,2-c][1]oxacycloundecin-6-one
• 6H-4,7-Methenofuro[3,2-c]oxacycloundecin-6-one, 4,8,9,12-tetrahydro-3,11-dimethyl-, [R-(E)]-
• CHEBI:69074
• 6H-4,7-Methenofuro(3,2-c)oxacycloundecin-6-one, 4,8,9,12-tetrahydro-3,11-dimethyl-, (R-(E))-
• CHEMBL1080239
• LWCKQMHMTSRRAA-QGQQYVBWSA-N
• (1R,8E)-3,8-dimethyl-5,14-dioxatricyclo[10.2.1.02,6]pentadeca-2(6),3,8,12(15)-tetraen-13-one
• HY-N0781
• AKOS015897170
• NCGC00385309-01
• AC-34847
• MS-23457
• CS-0009799
• A14500
• C17425
• Q27137414
• (1R,8E)-3,8-dimethyl-5,14-dioxatricyclo[10.2.1.0?,?]pentadeca-2(6),3,8,12(15)-tetraen-13-one
• 6H-4,7-Methenofuro(3,2-c)oxacycloundecin-6-one, 4,8,9,12-tetrahydro-3,11-dimethyl-, (4R,10E)-
• Germacra-1(10),4,7,11-tetraen-15-oic acid, 8,12-epoxy-6.alpha.-hydroxy-, .gamma.-lactone, (E)-()-
• Germacra-1(10),4,7,11-tetraen-15-oic acid, 8,12-epoxy-6.alpha.-hydroxy-, .gamma.-lactone, (E)-(+)-
• Germacra-1(10),4,7,11-tetraen-15-oic acid, 8,12-epoxy-6alpha-hydroxy-, gamma-lactone, (E)-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8497	84.97%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5896	58.96%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9341	93.41%
OATP1B3 inhibitior	+	0.9577	95.77%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.6607	66.07%
P-glycoprotein inhibitior	-	0.9120	91.20%
P-glycoprotein substrate	-	0.9088	90.88%
CYP3A4 substrate	+	0.5217	52.17%
CYP2C9 substrate	-	0.6065	60.65%
CYP2D6 substrate	-	0.8616	86.16%
CYP3A4 inhibition	-	0.7446	74.46%
CYP2C9 inhibition	-	0.7953	79.53%
CYP2C19 inhibition	-	0.6684	66.84%
CYP2D6 inhibition	-	0.8592	85.92%
CYP1A2 inhibition	+	0.7941	79.41%
CYP2C8 inhibition	-	0.7978	79.78%
CYP inhibitory promiscuity	-	0.7824	78.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5792	57.92%
Eye corrosion	-	0.9327	93.27%
Eye irritation	-	0.8105	81.05%
Skin irritation	-	0.6544	65.44%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6222	62.22%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5717	57.17%
skin sensitisation	-	0.6393	63.93%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5404	54.04%
Acute Oral Toxicity (c)	III	0.4026	40.26%
Estrogen receptor binding	-	0.7010	70.10%
Androgen receptor binding	-	0.5387	53.87%
Thyroid receptor binding	-	0.7412	74.12%
Glucocorticoid receptor binding	-	0.5868	58.68%
Aromatase binding	-	0.7010	70.10%
PPAR gamma	+	0.5976	59.76%
Honey bee toxicity	-	0.8707	87.07%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.24%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.79%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.20%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.95%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.45%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.36%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.28%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.44%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	82.62%	94.73%

Plants that contains it

• Aconitum japonicum subsp. subcuneatum
• Castanea dentata
• Elaphoglossum lindbergii
• Ferula ammoniacum
• Leucocarpus perfoliatus
• Lindera aggregata
• Lindera chunii
• Myrsine melanophloeos
• Neolitsea cassia
• Neolitsea daibuensis
• Neolitsea hiiranensis
• Neolitsea parvigemma
• Neolitsea villosa
• Pistacia atlantica
• Rogeria adenophylla
• Scrophularia buergeriana
• Stemodia maritima
• Trifolium hybridum

Cross-Links

• PubChem: 6450191
• NPASS: NPC216810
• LOTUS: LTS0251917
• wikiData: Q27137414