Pantolactone

Details

• Internal ID: f31af670-407f-4bfc-9855-1b56f45a1fd3
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3R)-3-hydroxy-4,4-dimethyloxolan-2-one
• SMILES (Canonical): CC1(COC(=O)C1O)C
• SMILES (Isomeric): CC1(COC(=O)[C@@H]1O)C
• InChI: InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
• InChI Key: SERHXTVXHNVDKA-BYPYZUCNSA-N
• Popularity: 274 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: 0.50
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 599-04-2
• PANTOLACTONE
• D-Pantolactone
• (R)-pantolactone
• (R)-3-Hydroxy-4,4-dimethyldihydrofuran-2(3H)-one
• D-(-)-Pantoyl Lactone
• (R)-Pantoyl lactone
• Pantothenic lactone
• pantoyl lactone
• 2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl-, (3R)-
• (R)-(-)-Pantolactone
• Pantolactone, (R)-
• (3R)-3-hydroxy-4,4-dimethyloxolan-2-one
• Pantoic acid gamma-lactone
• UNII-J288D7O0JS
• (3R)-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone
• J288D7O0JS
• (R)-(-)-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone
• EINECS 209-963-3
• 2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl-, (R)-
• EC 209-963-3
• (-)-2-Hydroxy-3,3-dimethyl-.gamma.-butyrolacton
• alpha-Hydroxy-beta,beta-dimethyl-gamma-butyrolactone
• Pantolyl lactone
• (D)-Pantolactone
• 2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl-, D-(-)-
• (3R)-3-hydroxy-4,4-dimethyl-tetrahydrofuran-2-one
• D-(-)-Pantolyl lactone
• D-(-)-Pantoic acid lactone
• MFCD00005392
• D-(?)-Pantolactone
• (R)-(-)pantolactone
• D(-)-2-Hydroxy-3,3-dimethyl-.gamma.-butyrolactone
• PANTOLACTONE [MI]
• bmse000381
• PANTOLACTONE [INCI]
• 3-Hydroxy-4,4-dimethyldihydro-2(3H)-furanone-, D-(-)- #
• PANTOLACTONE [USP-RS]
• PANTOLACTONE, (-)-
• PANTOLACTONE, R-ISOMER
• D-(-)-Pantolactone, 99%
• D-(-)-.alpha.Hydroxy-.beta.,.beta.-dimethyl-.gamma.-butyrolactone
• SCHEMBL1164270
• CHEMBL4587869
• PANTOLACTONE, R-(-)-
• CHEBI:16719
• DTXSID90881249
• AC1149
• s6027
• AKOS006238310
• CS-W011112
• HY-W010396
• AS-14054
• P0011
• (3R)-4,4-dimethyl-3-oxidanyl-oxolan-2-one
• EN300-67110
• C01012
• Dihydro-3-hydroxy-4H-dimethyl-2(3H)-furanone
• alpha-hydroxy-beta,beta-dimethyl-?-butyrolactone
• D-(-)-Pantolactone, puriss., >=99.0% (T)
• (R)-3-Hydroxy-4,4-dimethyl-dihydro-furan-2-one
• dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone
• D-(-)-2-Hydroxy-3,3-dimethyl-gamma-butyrolactone
• Q-200920
• (3R)-3-hydroxy-4,4-dimethyldihydrofuran-2(3H)-one
• (R)-3-hydroxy-4,4-dimethyl-dihydrofuran-2(3H)-one
• Q27102042
• Z1065885480
• (3R)-TETRAHYDRO-3-HYDROXY-4,4-DIMETHYLFURAN-2-ONE
• D-(-)-4-Hydroxyphenylglycine dane salt (methyl potassium)
• 2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl-, (theta)-
• (3R)-3-Hydroxy-4,4-dimethyldihydrofuran-2(3H)-one (Pantolactone)
• Pantolactone, United States Pharmacopeia (USP) Reference Standard
• (R)-.ALPHA.-HYDROXY-.BETA.,.BETA.-DIMETHYL-.GAMMA.-BUTYROLACTONE
• D-(-)-.ALPHA.-HYDROXY-.BETA.,.BETA.-DIMETHYL-.GAMMA.-BUTYROLACTONE
• Pantolactone, Pharmaceutical Secondary Standard; Certified Reference Material
• (R)-(-)-Pantolactone Pantoic acid gamma-lactone (R)-(-)-beta,beta-Dimethyl-alpha-hydroxy-gamma-butyrolactone (R)-(-)-alpha-Hydroxy-beta,beta-dimethyl-gamma-butyrolactone (R)-(-)-4,5-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone D-(-)-alpha-Hydroxy-beta,beta-dimethyl-gamma-butyrolactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9496	94.96%
Caco-2	+	0.5505	55.05%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8157	81.57%
OATP2B1 inhibitior	-	0.8498	84.98%
OATP1B1 inhibitior	+	0.9674	96.74%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9112	91.12%
P-glycoprotein inhibitior	-	0.9822	98.22%
P-glycoprotein substrate	-	0.9568	95.68%
CYP3A4 substrate	-	0.6129	61.29%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.8691	86.91%
CYP3A4 inhibition	-	0.9392	93.92%
CYP2C9 inhibition	-	0.8531	85.31%
CYP2C19 inhibition	-	0.9053	90.53%
CYP2D6 inhibition	-	0.9448	94.48%
CYP1A2 inhibition	-	0.8343	83.43%
CYP2C8 inhibition	-	0.9956	99.56%
CYP inhibitory promiscuity	-	0.9335	93.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5451	54.51%
Eye corrosion	-	0.8458	84.58%
Eye irritation	+	0.9742	97.42%
Skin irritation	-	0.7100	71.00%
Skin corrosion	-	0.8253	82.53%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8400	84.00%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6302	63.02%
skin sensitisation	-	0.7121	71.21%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.7965	79.65%
Acute Oral Toxicity (c)	III	0.6162	61.62%
Estrogen receptor binding	-	0.8418	84.18%
Androgen receptor binding	-	0.7746	77.46%
Thyroid receptor binding	-	0.8746	87.46%
Glucocorticoid receptor binding	-	0.8420	84.20%
Aromatase binding	-	0.8860	88.60%
PPAR gamma	-	0.8923	89.23%
Honey bee toxicity	-	0.9228	92.28%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.6556	65.56%

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	93.53%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	90.10%	89.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.19%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.43%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.47%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.11%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.97%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.33%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.69%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.40%	99.23%

Plants that contains it

• Imperata cylindrica
• Ranunculus ternatus

Cross-Links

• PubChem: 439368
• NPASS: NPC87237