(4S,5R,6R)-Tetrahydro-4-hydroxy-3,3,5-trimethyl-6-[(E)-1-methyl-1-propenyl]-2H-pyran-2-one

Details

• Internal ID: 2b4e89c3-a2c0-4591-8e1b-d0d1d29619ba
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: (4S,5R,6R)-6-[(E)-but-2-en-2-yl]-4-hydroxy-3,3,5-trimethyloxan-2-one
• SMILES (Canonical): CC=C(C)C1C(C(C(C(=O)O1)(C)C)O)C
• SMILES (Isomeric): C/C=C(\C)/[C@H]1[C@@H]([C@@H](C(C(=O)O1)(C)C)O)C
• InChI: InChI=1S/C12H20O3/c1-6-7(2)9-8(3)10(13)12(4,5)11(14)15-9/h6,8-10,13H,1-5H3/b7-6+/t8-,9-,10-/m0/s1
• InChI Key: TXJOTIFCEKOXSM-WQPYABEOSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.28 g/mol
• Exact Mass: 212.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (4S)-3,3,5beta-Trimethyl-4beta-hydroxy-6alpha-(1-methyl-1-propenyl)tetrahydro-2H-pyran-2-one
• (4S,5R,6R)-Tetrahydro-4-hydroxy-3,3,5-trimethyl-6-[(E)-1-methyl-1-propenyl]-2H-pyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9805	98.05%
Caco-2	+	0.7000	70.00%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8156	81.56%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.8436	84.36%
OATP1B3 inhibitior	+	0.9751	97.51%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7645	76.45%
P-glycoprotein inhibitior	-	0.9315	93.15%
P-glycoprotein substrate	-	0.9358	93.58%
CYP3A4 substrate	-	0.5435	54.35%
CYP2C9 substrate	-	0.8111	81.11%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.9131	91.31%
CYP2C9 inhibition	-	0.8835	88.35%
CYP2C19 inhibition	-	0.8040	80.40%
CYP2D6 inhibition	-	0.9660	96.60%
CYP1A2 inhibition	-	0.9086	90.86%
CYP2C8 inhibition	-	0.9812	98.12%
CYP inhibitory promiscuity	-	0.8710	87.10%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8056	80.56%
Carcinogenicity (trinary)	Non-required	0.5321	53.21%
Eye corrosion	-	0.8683	86.83%
Eye irritation	-	0.6639	66.39%
Skin irritation	+	0.7537	75.37%
Skin corrosion	-	0.8924	89.24%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5529	55.29%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.7146	71.46%
skin sensitisation	+	0.5350	53.50%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	+	0.6766	67.66%
Acute Oral Toxicity (c)	III	0.6898	68.98%
Estrogen receptor binding	-	0.7529	75.29%
Androgen receptor binding	-	0.7202	72.02%
Thyroid receptor binding	-	0.6661	66.61%
Glucocorticoid receptor binding	-	0.8374	83.74%
Aromatase binding	-	0.8395	83.95%
PPAR gamma	-	0.6486	64.86%
Honey bee toxicity	-	0.8680	86.80%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7781	77.81%

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	91.82%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	85.58%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.56%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	83.09%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.72%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.50%	99.23%

Plants that contains it

• Acacia confusa
• Erica arborea
• Erica arborea
• Isodon lihsienensis
• Phoebe clemensii

Cross-Links

• PubChem: 14376452
• NPASS: NPC104738
• LOTUS: LTS0255044
• wikiData: Q105266785