(3E)-3-[2-[(1R,3R,4aS,8aR)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethylidene]oxolan-2-one

Details

• Internal ID: 5dbfcf82-3a5b-4aff-981c-f60cfe281cec
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3E)-3-[2-[(1R,3R,4aS,8aR)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethylidene]oxolan-2-one
• SMILES (Canonical): CC1(CCCC2(C1C(=O)C(C(=C)C2CC=C3CCOC3=O)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1C(=O)[C@@H](C(=C)[C@@H]2C/C=C/3\CCOC3=O)O)(C)C
• InChI: InChI=1S/C20H28O4/c1-12-14(7-6-13-8-11-24-18(13)23)20(4)10-5-9-19(2,3)17(20)16(22)15(12)21/h6,14-15,17,21H,1,5,7-11H2,2-4H3/b13-6+/t14-,15+,17-,20+/m0/s1
• InChI Key: LAIHLMZBILKPIA-VDNUWSFTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9782	97.82%
Caco-2	+	0.5133	51.33%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8384	83.84%
OATP2B1 inhibitior	-	0.8637	86.37%
OATP1B1 inhibitior	+	0.8288	82.88%
OATP1B3 inhibitior	+	0.8947	89.47%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	+	0.5845	58.45%
P-glycoprotein inhibitior	-	0.6423	64.23%
P-glycoprotein substrate	-	0.8241	82.41%
CYP3A4 substrate	+	0.6312	63.12%
CYP2C9 substrate	-	0.7957	79.57%
CYP2D6 substrate	-	0.9003	90.03%
CYP3A4 inhibition	-	0.6337	63.37%
CYP2C9 inhibition	-	0.8067	80.67%
CYP2C19 inhibition	-	0.8329	83.29%
CYP2D6 inhibition	-	0.9247	92.47%
CYP1A2 inhibition	-	0.7607	76.07%
CYP2C8 inhibition	-	0.7214	72.14%
CYP inhibitory promiscuity	-	0.8517	85.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5896	58.96%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8925	89.25%
Skin irritation	+	0.5917	59.17%
Skin corrosion	-	0.9250	92.50%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5131	51.31%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5196	51.96%
skin sensitisation	-	0.8244	82.44%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4867	48.67%
Acute Oral Toxicity (c)	III	0.7796	77.96%
Estrogen receptor binding	+	0.7302	73.02%
Androgen receptor binding	+	0.7063	70.63%
Thyroid receptor binding	+	0.6330	63.30%
Glucocorticoid receptor binding	+	0.7748	77.48%
Aromatase binding	+	0.5772	57.72%
PPAR gamma	-	0.5070	50.70%
Honey bee toxicity	-	0.8076	80.76%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9973	99.73%

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	97.60%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.24%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.46%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.28%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.42%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.05%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	82.92%	94.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.49%	92.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.44%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.28%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.31%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.24%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.36%	95.89%

Plants that contains it

• Acacia linarioides
• Anadenanthera colubrina
• Aquilegia viridiflora
• Astragalus kabadianus
• Brombya platynema
• Cerbera odollam
• Cichorium endivia
• Clinopodium gracile
• Coelogyne prolifera
• Daphne arisanensis
• Denhamia disperma
• Guadua angustifolia
• Hedychium coronarium
• Jaborosa leucotricha
• Kiggelaria africana
• Lippia abyssinica
• Lupinus luteus
• Morinda morindoides
• Perymenium jelskii
• Phenax angustifolius
• Potentilla candicans
• Prunus mahaleb
• Rhamnus cathartica
• Rhamnus formosana
• Senecio ruwenzoriensis
• Senna didymobotrya
• Spiraea formosana
• Strychnos elaeocarpa
• Strychnos wallichiana
• Tinadendron noumeanum
• Trichilia havanensis
• Tripterospermum lanceolatum
• Vachellia leucophloea
• Veronica liwanensis
• Viburnum betulifolium

Cross-Links

• PubChem: 21601997
• NPASS: NPC108292
• LOTUS: LTS0072193
• wikiData: Q105148661