Pisolactone

Details

• Internal ID: 9ebcf1f5-e0e6-41f7-adcf-cd85bcd638ce
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,5S)-5-[(1S)-1-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-propan-2-yloxolan-2-one
• SMILES (Canonical): CC(C)C1CC(OC1=O)C(C)C2CCC3(C2(CCC4=C3CCC5C4(CCC(C5(C)C)O)C)C)C
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C)[C@@H]5C[C@@H](C(=O)O5)C(C)C
• InChI: InChI=1S/C31H50O3/c1-18(2)20-17-24(34-27(20)33)19(3)21-11-15-31(8)23-9-10-25-28(4,5)26(32)13-14-29(25,6)22(23)12-16-30(21,31)7/h18-21,24-26,32H,9-17H2,1-8H3/t19-,20+,21+,24-,25-,26-,29+,30+,31-/m0/s1
• InChI Key: TWOLTMVJWNRWJQ-DXDFVCSKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.70 g/mol
• Exact Mass: 470.37599545 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 7.80
• Atomic LogP (AlogP): 7.32
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Pisolactone-
• UET6Z5DQ5J
• UNII-UET6Z5DQ5J
• 87164-33-8
• (3R,5S)-5-((1S)-1-((3S,5R,10S,13R,14R,17R)-3-Hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-17-yl)ethyl)-3-isopropyl-tetrahydrofuran-2-one
• Lanost-8-ene-24-carboxylic acid, 3,22-dihydroxy-, gamma-lactone, (3beta,22S,24R)-
• LANOST-8-ENE-24-CARBOXYLIC ACID, 3,22-DIHYDROXY-, .GAMMA.-LACTONE, (3.BETA.,22S,24R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	+	0.5256	52.56%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8088	80.88%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.8723	87.23%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	+	0.8839	88.39%
P-glycoprotein inhibitior	+	0.5881	58.81%
P-glycoprotein substrate	-	0.6260	62.60%
CYP3A4 substrate	+	0.6632	66.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8395	83.95%
CYP3A4 inhibition	-	0.6274	62.74%
CYP2C9 inhibition	-	0.8666	86.66%
CYP2C19 inhibition	-	0.7364	73.64%
CYP2D6 inhibition	-	0.9387	93.87%
CYP1A2 inhibition	-	0.7722	77.22%
CYP2C8 inhibition	-	0.6567	65.67%
CYP inhibitory promiscuity	-	0.8589	85.89%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5379	53.79%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9155	91.55%
Skin irritation	+	0.6205	62.05%
Skin corrosion	-	0.9280	92.80%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4331	43.31%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5165	51.65%
skin sensitisation	-	0.6477	64.77%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5796	57.96%
Acute Oral Toxicity (c)	III	0.6361	63.61%
Estrogen receptor binding	+	0.7321	73.21%
Androgen receptor binding	+	0.7611	76.11%
Thyroid receptor binding	+	0.6424	64.24%
Glucocorticoid receptor binding	+	0.8594	85.94%
Aromatase binding	+	0.7102	71.02%
PPAR gamma	+	0.6152	61.52%
Honey bee toxicity	-	0.7450	74.50%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9927	99.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.84%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.02%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	89.84%	92.78%
CHEMBL2581	P07339	Cathepsin D	89.58%	98.95%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.48%	90.08%
CHEMBL1937	Q92769	Histone deacetylase 2	89.45%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.95%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.65%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.63%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.25%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.71%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.22%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.30%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.05%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.00%	97.25%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.41%	95.71%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.01%	85.11%
CHEMBL221	P23219	Cyclooxygenase-1	81.46%	90.17%
CHEMBL259	P32245	Melanocortin receptor 4	80.65%	95.38%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.59%	93.03%
CHEMBL1871	P10275	Androgen Receptor	80.58%	96.43%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.46%	94.33%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.31%	91.38%

Plants that contains it

• Alcea rosea
• Alpinia roxburghii
• Balanops australiana
• Davallia perdurans
• Euonymus tingens
• Euphorbia cornigera
• Gonzalezia decurrens
• Hylocomium splendens
• Kokoona reflexa
• Maesa ramentacea
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense

Cross-Links

• PubChem: 14167274
• NPASS: NPC206280
• LOTUS: LTS0022480
• wikiData: Q77376319