Villosin

Details

• Internal ID: a3ca09e4-88a3-4a0f-9e63-1b3442ada4b5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2C=CC3=CCOC3=O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CCC(=C)[C@@H]2/C=C/C3=CCOC3=O)(C)C
• InChI: InChI=1S/C20H28O2/c1-14-6-9-17-19(2,3)11-5-12-20(17,4)16(14)8-7-15-10-13-22-18(15)21/h7-8,10,16-17H,1,5-6,9,11-13H2,2-4H3/b8-7+/t16-,17-,20+/m0/s1
• InChI Key: HVTQZHAAIRBKHO-YSLAMIOMSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.40 g/mol
• Exact Mass: 300.208930132 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.82
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 160598-92-5
• 4-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one
• CHEMBL1099266
• AKOS040762490
• (11E)-15,16-Epoxylabda-8(20),11,13-trien-16-one
• 15-Hydroxylabda-8(20),11,13-trien-16-oic acid lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	+	0.6961	69.61%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5482	54.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8721	87.21%
OATP1B3 inhibitior	+	0.8458	84.58%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.5607	56.07%
P-glycoprotein inhibitior	-	0.6848	68.48%
P-glycoprotein substrate	-	0.8665	86.65%
CYP3A4 substrate	+	0.6167	61.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8851	88.51%
CYP3A4 inhibition	-	0.7593	75.93%
CYP2C9 inhibition	-	0.7810	78.10%
CYP2C19 inhibition	+	0.7139	71.39%
CYP2D6 inhibition	-	0.8925	89.25%
CYP1A2 inhibition	+	0.5533	55.33%
CYP2C8 inhibition	-	0.5920	59.20%
CYP inhibitory promiscuity	-	0.7337	73.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5557	55.57%
Eye corrosion	-	0.9740	97.40%
Eye irritation	-	0.8835	88.35%
Skin irritation	-	0.6210	62.10%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7609	76.09%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5019	50.19%
skin sensitisation	-	0.5439	54.39%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6472	64.72%
Acute Oral Toxicity (c)	III	0.7320	73.20%
Estrogen receptor binding	-	0.4834	48.34%
Androgen receptor binding	-	0.5097	50.97%
Thyroid receptor binding	+	0.6554	65.54%
Glucocorticoid receptor binding	+	0.6287	62.87%
Aromatase binding	+	0.6473	64.73%
PPAR gamma	+	0.6340	63.40%
Honey bee toxicity	-	0.8115	81.15%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
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	97.99%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.53%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.31%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.35%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.15%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.01%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.28%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.89%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.12%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.33%	82.69%
CHEMBL1977	P11473	Vitamin D receptor	83.04%	99.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.86%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.77%	94.75%

Plants that contains it

• Acacia linarioides
• Anadenanthera colubrina
• Aquilegia viridiflora
• Astragalus kabadianus
• Brombya platynema
• Cerbera odollam
• Cichorium endivia
• Clinopodium gracile
• Coelogyne prolifera
• Curcuma comosa
• Daphne arisanensis
• Denhamia disperma
• Guadua angustifolia
• Hedychium coronarium
• Hedychium gardnerianum
• Hedychium villosum
• Jaborosa leucotricha
• Kiggelaria africana
• Lippia abyssinica
• Lupinus luteus
• Morinda morindoides
• Perymenium jelskii
• Phenax angustifolius
• Potentilla candicans
• Prunus mahaleb
• Punica granatum
• 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: 16733738
• NPASS: NPC4509
• LOTUS: LTS0042967
• wikiData: Q105300097