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

Details

• Internal ID: 00a55f9c-b58c-44a7-9281-bd438b77a287
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2S)-3-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2-hydroxy-2H-furan-5-one
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2C=CC3=CC(=O)OC3O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CCC(=C)[C@@H]2/C=C/C3=CC(=O)O[C@@H]3O)(C)C
• InChI: InChI=1S/C20H28O3/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/h7-8,12,15-16,18,22H,1,5-6,9-11H2,2-4H3/b8-7+/t15-,16-,18-,20+/m0/s1
• InChI Key: KJUPGEKTXQYTSU-MMLWSDKNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.14
• 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	+	0.9946	99.46%
Caco-2	+	0.4883	48.83%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4947	49.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8251	82.51%
OATP1B3 inhibitior	-	0.2342	23.42%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.7005	70.05%
P-glycoprotein inhibitior	-	0.8380	83.80%
P-glycoprotein substrate	-	0.8549	85.49%
CYP3A4 substrate	+	0.6414	64.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8929	89.29%
CYP3A4 inhibition	-	0.7251	72.51%
CYP2C9 inhibition	-	0.7895	78.95%
CYP2C19 inhibition	-	0.6306	63.06%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	+	0.5718	57.18%
CYP2C8 inhibition	-	0.6618	66.18%
CYP inhibitory promiscuity	-	0.8744	87.44%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5619	56.19%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.9300	93.00%
Skin irritation	+	0.5152	51.52%
Skin corrosion	-	0.9230	92.30%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7060	70.60%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.5456	54.56%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5251	52.51%
Acute Oral Toxicity (c)	III	0.4709	47.09%
Estrogen receptor binding	+	0.7880	78.80%
Androgen receptor binding	+	0.5329	53.29%
Thyroid receptor binding	+	0.6630	66.30%
Glucocorticoid receptor binding	+	0.7425	74.25%
Aromatase binding	+	0.7106	71.06%
PPAR gamma	+	0.7781	77.81%
Honey bee toxicity	-	0.8301	83.01%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.06%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.12%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.27%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.17%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	87.62%	94.75%
CHEMBL1977	P11473	Vitamin D receptor	87.39%	99.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.96%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.33%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	84.91%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.62%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.90%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.84%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.19%	93.40%
CHEMBL1871	P10275	Androgen Receptor	81.60%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.04%	86.33%
CHEMBL325	Q13547	Histone deacetylase 1	80.05%	95.92%

Plants that contains it

• Acacia linarioides
• Alpinia chinensis
• Anadenanthera colubrina
• Aquilegia viridiflora
• Astragalus kabadianus
• Brombya platynema
• Cerbera odollam
• Cichorium endivia
• Clinopodium gracile
• Coelogyne prolifera
• Daphne arisanensis
• Denhamia disperma
• Etlingera elatior
• 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: 92466427
• NPASS: NPC261747
• LOTUS: LTS0126384
• wikiData: Q105141974