Mevalonolactone

Details

• Internal ID: 555dd604-e754-4d29-8ae6-96980589f2fd
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: (4R)-4-hydroxy-4-methyloxan-2-one
• SMILES (Canonical): CC1(CCOC(=O)C1)O
• SMILES (Isomeric): C[C@]1(CCOC(=O)C1)O
• InChI: InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m1/s1
• InChI Key: JYVXNLLUYHCIIH-ZCFIWIBFSA-N
• Popularity: 202 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14 g/mol
• Exact Mass: 130.062994177 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Mevalonolactone
• (R)-4-Hydroxy-4-methyltetrahydro-2H-pyran-2-one
• (-)-Mevalonolactone
• (R)-(-)-Mevalonolactone
• Adeka mevalonolactone
• (3R)-Mevalonolactone
• Mevalonolactone, (-)-
• (-)-(R)-Mevalonic acid lactone
• (-)-(R)-Mevalonolactone
• 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (4R)-
• 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-
• Mevalonic acid lactone
• Mevalonic-D, L acid lactone
• UNII-661X270Z3L
• CHEBI:67849
• 661X270Z3L
• (R)-(-)-3-Hydroxy-3-methyl-5-pentanolide
• D-Mevalonic Acid Lactone
• r-mevalonolactone
• D-Mevalonolactone
• Prestwick_97
• R(-)Mevalonolactone
• (4R)-4-hydroxy-4-methyloxan-2-one
• Prestwick0_000750
• Prestwick1_000750
• Prestwick2_000750
• SCHEMBL879
• R-mevalonolactone, (-)-
• D,L-mevalonic-acid-lactone
• MEVALONOLACTONE [INCI]
• SPBio_002679
• CHEMBL1401520
• JYVXNLLUYHCIIH-ZCFIWIBFSA-N
• HMS1570E22
• MFCD01074894
• AKOS017343730
• SB47779
• (R)-3-hydroxy-3-methyl-5-pentanolide
• NCGC00016531-01
• CAS-674-26-0
• R)-(-)-3-Hydroxy-3-methyl-5-pentanolide
• (R)-(-)-Mevalonolactone, >=90.0% (GC)
• M-6701
• A937707
• Q27136326

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	+	0.8231	82.31%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8582	85.82%
OATP2B1 inhibitior	-	0.8480	84.80%
OATP1B1 inhibitior	+	0.9464	94.64%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7352	73.52%
BSEP inhibitior	-	0.9274	92.74%
P-glycoprotein inhibitior	-	0.9831	98.31%
P-glycoprotein substrate	-	0.9806	98.06%
CYP3A4 substrate	-	0.5842	58.42%
CYP2C9 substrate	-	0.7974	79.74%
CYP2D6 substrate	-	0.8655	86.55%
CYP3A4 inhibition	-	0.9649	96.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9608	96.08%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9910	99.10%
CYP inhibitory promiscuity	-	0.9952	99.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6207	62.07%
Eye corrosion	-	0.8736	87.36%
Eye irritation	+	0.9829	98.29%
Skin irritation	-	0.6154	61.54%
Skin corrosion	-	0.9250	92.50%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7495	74.95%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.6409	64.09%
skin sensitisation	-	0.8885	88.85%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	+	0.8991	89.91%
Acute Oral Toxicity (c)	III	0.5555	55.55%
Estrogen receptor binding	-	0.9575	95.75%
Androgen receptor binding	-	0.8842	88.42%
Thyroid receptor binding	-	0.9064	90.64%
Glucocorticoid receptor binding	-	0.9182	91.82%
Aromatase binding	-	0.8909	89.09%
PPAR gamma	-	0.9136	91.36%
Honey bee toxicity	-	0.9705	97.05%
Biodegradation	+	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.4867	48.67%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3397	P11712	Cytochrome P450 2C9	12589.3 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	14125.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.01%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.45%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.81%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.20%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.12%	86.33%
CHEMBL2581	P07339	Cathepsin D	80.98%	98.95%

Plants that contains it

• Clausena heptaphylla
• Sarcomelicope glauca
• Stemona japonica

Cross-Links

• PubChem: 6419891
• NPASS: NPC133771
• ChEMBL: CHEMBL1401520
• LOTUS: LTS0037366
• wikiData: Q27136326