Petasitolone

Details

• Internal ID: 0ae0c30d-8eac-41f1-ad16-d6c196d0b90d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4aR,5S,8aR)-3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one
• SMILES (Canonical): CC1CCCC2C1(C=C(C(=O)C2)C(C)(C)O)C
• SMILES (Isomeric): C[C@H]1CCC[C@H]2[C@@]1(C=C(C(=O)C2)C(C)(C)O)C
• InChI: InChI=1S/C15H24O2/c1-10-6-5-7-11-8-13(16)12(14(2,3)17)9-15(10,11)4/h9-11,17H,5-8H2,1-4H3/t10-,11+,15+/m0/s1
• InChI Key: LYFRYUAWUBLCKH-FIXISWKDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.35 g/mol
• Exact Mass: 236.177630004 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• UNII-05X5L9F9XM
• 05X5L9F9XM
• 35124-22-2
• 2(1H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4aR,5S,8aR)-
• 2(1H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4ar-(4aalpha,5alpha,8aalpha))-
• DTXSID30188628
• CHEBI:173720
• (4aR,5S,8aR)-3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one
• Q27236148
• 2(1H)-NAPHTHALENONE, 4A,5,6,7,8,8A-HEXAHYDRO-3-(1-HYDROXY-1-METHYLETHYL)-4A,5-DIMETHYL-, (4AR-(4A.ALPHA.,5.ALPHA.,8A.ALPHA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	+	0.8772	87.72%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6792	67.92%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.8899	88.99%
P-glycoprotein inhibitior	-	0.8980	89.80%
P-glycoprotein substrate	-	0.8693	86.93%
CYP3A4 substrate	+	0.5224	52.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8767	87.67%
CYP3A4 inhibition	-	0.8481	84.81%
CYP2C9 inhibition	-	0.8500	85.00%
CYP2C19 inhibition	-	0.6124	61.24%
CYP2D6 inhibition	-	0.9589	95.89%
CYP1A2 inhibition	-	0.6708	67.08%
CYP2C8 inhibition	-	0.9096	90.96%
CYP inhibitory promiscuity	-	0.8506	85.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5043	50.43%
Eye corrosion	-	0.9912	99.12%
Eye irritation	+	0.6628	66.28%
Skin irritation	+	0.6610	66.10%
Skin corrosion	-	0.9710	97.10%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6308	63.08%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	+	0.6658	66.58%
skin sensitisation	+	0.6069	60.69%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4654	46.54%
Acute Oral Toxicity (c)	III	0.7711	77.11%
Estrogen receptor binding	-	0.6489	64.89%
Androgen receptor binding	-	0.7376	73.76%
Thyroid receptor binding	+	0.6660	66.60%
Glucocorticoid receptor binding	-	0.5099	50.99%
Aromatase binding	-	0.6959	69.59%
PPAR gamma	-	0.7592	75.92%
Honey bee toxicity	-	0.9395	93.95%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9875	98.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.85%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.98%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	92.51%	97.05%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.01%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.70%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.08%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.52%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.60%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.54%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.95%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.90%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.89%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.80%	93.03%

Plants that contains it

• Acacia paradoxa
• Adonis sutchuenensis
• Astragalus ernestii
• Berneuxia thibetica
• Bongardia chrysogonum
• Eragrostis curvula
• Fritillaria meleagris
• Isophysis tasmanica
• Ligularia subspicata
• Matricaria discoidea
• Metasequoia glyptostroboides
• Petasites japonicus
• Philenoptera laxiflora
• Plantago lundborgii
• Sideritis arborescens
• Solanum pseudoquina
• Triadica sebifera

Cross-Links

• PubChem: 5320506
• NPASS: NPC394
• LOTUS: LTS0155597
• wikiData: Q27236148