(3E,5R)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-hydroxyoxolan-2-one

Details

• Internal ID: 6dbe986c-571a-478f-bd80-69d712f1ed59
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3E,5R)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-hydroxyoxolan-2-one
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2CC=C3CC(OC3=O)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CCC(=C)[C@@H]2C/C=C/3\C[C@@H](OC3=O)O)(C)C
• InChI: InChI=1S/C20H30O3/c1-13-6-9-16-19(2,3)10-5-11-20(16,4)15(13)8-7-14-12-17(21)23-18(14)22/h7,15-17,21H,1,5-6,8-12H2,2-4H3/b14-7+/t15-,16-,17+,20+/m0/s1
• InChI Key: DYYYQLXAGIXUGM-JHZATVQFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.37
• H-Bond Acceptor: 3
• 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	+	0.9956	99.56%
Caco-2	+	0.6313	63.13%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5024	50.24%
OATP2B1 inhibitior	-	0.8635	86.35%
OATP1B1 inhibitior	+	0.8335	83.35%
OATP1B3 inhibitior	+	0.8175	81.75%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7496	74.96%
P-glycoprotein inhibitior	-	0.6461	64.61%
P-glycoprotein substrate	-	0.8623	86.23%
CYP3A4 substrate	+	0.6543	65.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8783	87.83%
CYP3A4 inhibition	-	0.6041	60.41%
CYP2C9 inhibition	-	0.8529	85.29%
CYP2C19 inhibition	-	0.7493	74.93%
CYP2D6 inhibition	-	0.9526	95.26%
CYP1A2 inhibition	-	0.7410	74.10%
CYP2C8 inhibition	-	0.7405	74.05%
CYP inhibitory promiscuity	-	0.9137	91.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5924	59.24%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9112	91.12%
Skin irritation	+	0.5661	56.61%
Skin corrosion	-	0.9141	91.41%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7336	73.36%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.6130	61.30%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5200	52.00%
Acute Oral Toxicity (c)	I	0.5080	50.80%
Estrogen receptor binding	+	0.6417	64.17%
Androgen receptor binding	+	0.6365	63.65%
Thyroid receptor binding	+	0.6636	66.36%
Glucocorticoid receptor binding	+	0.7676	76.76%
Aromatase binding	+	0.6858	68.58%
PPAR gamma	+	0.5930	59.30%
Honey bee toxicity	-	0.8395	83.95%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9970	99.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.88%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.42%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.36%	98.95%
CHEMBL1977	P11473	Vitamin D receptor	91.09%	99.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.59%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.89%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.66%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	86.12%	83.82%
CHEMBL1902	P62942	FK506-binding protein 1A	85.85%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.95%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.54%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.54%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.02%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.02%	93.03%

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
• Zingiber ottensii

Cross-Links

• PubChem: 92983345
• NPASS: NPC108758
• LOTUS: LTS0269685
• wikiData: Q104991653