Gluconolactone

Details

• Internal ID: 9bca9569-1de4-4bfa-9e31-5a29fa95d15f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Hexoses > Gluconolactones
• IUPAC Name: (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• SMILES (Canonical): C(C1C(C(C(C(=O)O1)O)O)O)O
• SMILES (Isomeric): C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O
• InChI: InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1
• InChI Key: PHOQVHQSTUBQQK-SQOUGZDYSA-N
• Popularity: 1,880 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14 g/mol
• Exact Mass: 178.04773803 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -3.01
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• delta-gluconolactone
• 90-80-2
• D-glucono-1,5-lactone
• Gluconic acid lactone
• 1,5-Gluconolactone
• Glucono delta-lactone
• D-Gluconolactone
• d-(+)-Glucono-1,5-lactone
• D-Gluconic acid lactone
• D-Gluconic acid delta-lactone
• 1,5-D-Gluconolactone
• Gluconic lactone
• Glucono delta lactone
• Gluconic delta-lactone
• (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one
• D-delta-Gluconolactone
• delta-D-Gluconolactone
• Deltagluconolactone
• Fujiglucon
• D-Gluconic delta-lactone
• glucono-delta-lactone
• (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• Glucarolactone
• beta-Glucono-1,5-lactone
• Lysactone
• D-Aldonolactone
• Riken lactone
• D-(+)-Gluconic acid delta-lactone
• D-Gluconic acid-delta-lactone
• Gluconolactone [USP]
• HSDB 488
• UNII-WQ29KQ9POT
• WQ29KQ9POT
• AI3-19578
• EINECS 202-016-5
• D-threo-Aldono-1,5-lactone
• INS NO.575
• 1335-57-5
• DTXSID0026549
• glucono-1,5-lactone
• CHEBI:16217
• INS-575
• D-Gluconic acid, delta-lactone
• Gluconic Acid Anhydride
• Gluconic acid, delta-lactone, D-
• Glucono .delta. lactone
• Glucono .delta.-lactone
• .delta.-D-Gluconolactone
• NSC 34393
• NSC-34393
• 4253-68-3
• NSC-758238
• Gluconic Acid delta-Lactone
• GLUCONO-DELTA LACTONE
• Gluconic acid lactone (6CI)
• DTXCID406549
• E-575
• d-Gluconic acid .delta.-lactone
• EC 202-016-5
• Gluconolactone (USP)
• RENACIDIN COMPONENT GLUCONOLACTONE
• D-glucono-delta-lactone
• GLUCONOLACTONE COMPONENT OF RENACIDIN
• (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one
• GLUCONOLACTONE (II)
• GLUCONOLACTONE [II]
• 135820-79-0
• GDL
• GLUCONOLACTONE (MART.)
• GLUCONOLACTONE [MART.]
• GLUCONOLACTONE (USP-RS)
• GLUCONOLACTONE [USP-RS]
• 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one
• D-Gluconic acid, .delta.-lactone
• Glucolactone
• d-gluconic acid d-lactone
• GLUCONOLACTONE (USP MONOGRAPH)
• GLUCONOLACTONE [USP MONOGRAPH]
• CAS-90-80-2
• .delta.-Gluconolactone
• LGC
• D-Gluconic acid-1,5-lactone
• gluconolactones
• NSC34393
• Glucono--Lactone
• gluconodeltalactone
• delta-Aldonolactone
• Gluconate, lactone
• NCGC00095002-01
• delta gluconolactone
• gamma-Gluconolactone
• D-Glucono-d-lactone
• MFCD00006647
• Glucono gamma-lactone
• Glucono 1,5-lactone
• D-glucon-1,5-lacton
• D-glucono1,5-lactone
• gluconic acid d-lactone
• delta-delta-Gluconolactone
• 1,5-delta-Gluconolactone
• bmse000230
• D04QWD
• delta-Gluconic acid lactone
• delta-Glucono-delta-lactone
• GLUCONOLACTONE [MI]
• delta-Glucono-1,5-lactone
• delta-Gluconic delta-lactone
• Glucono-Delta-Lactone(GDL)
• SCHEMBL15320
• GLUCONOLACTONE [HSDB]
• GLUCONOLACTONE [INCI]
• delta-Gluconic acid d-lactone
• MLS002207105
• D-Gluconic acid 1,5-lactone
• D- glucono- 1, 5- lactone
• GLUCONOLACTONE [WHO-DD]
• CHEMBL1200829
• D-(+)-Gluconic acid d-lactone
• CHEBI:24267
• D-Gluconic acid, <V-lactone
• delta-Gluconic acid 1,5-lactone
• delta-Gluconic acid delta-lactone
• delta-Gluconic acid-1,5-lactone
• delta-Gluconic acid-delta-lactone
• PHOQVHQSTUBQQK-SQOUGZDYSA-N
• D(+)-Gluconic acid gamma-lactone
• Glucono-|A-lactone USP26 FCCIV
• CS-M3768
• D-(+)-Gluconic acid-delta lactone
• delta-(+)-Gluconic acid d-lactone
• GLUCONO DELTA-LACTONE [FCC]
• HY-I0301
• GLUCONOLACTONE [ORANGE BOOK]
• Tox21_111383
• Tox21_200429
• BDBM50366565
• GLUCONO-DELTA-LACTONE [VANDF]
• AKOS016843888
• Tox21_111383_1
• DB04564
• delta-(+)-Gluconic acid-delta lactone
• DS-4779
• LS-2264
• (3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-one
• NCGC00257983-01
• NCGC00344522-01
• AC-13150
• E575
• SMR001306715
• G0039
• EN300-97037
• C00198
• D04332
• P19765
• D-(+)-Gluconic acid delta-lactone, >=99.0%
• Gluconolactone, meets USP testing specifications
• Q114174
• W-100325
• 3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
• D-(+)-Gluconic acid delta-lactone, analytical standard
• Z1255427181
• A88519CB-A562-4C9C-B925-0A6B1701F841
• Gluconolactone, United States Pharmacopeia (USP) Reference Standard
• (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydropyran-2-one
• (3S,4R,5R,6S)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2-ONE; GLUCONOLACTONE
• D-GLUCONIC ACID DELTA-LACTONE(O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 793)
• GLUCONO DELTA LACTONE(O'Neil, M.J. (ed.). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 793)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8876	88.76%
Caco-2	-	0.9801	98.01%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7488	74.88%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9824	98.24%
P-glycoprotein inhibitior	-	0.9789	97.89%
P-glycoprotein substrate	-	0.9866	98.66%
CYP3A4 substrate	-	0.7047	70.47%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9594	95.94%
CYP2C9 inhibition	-	0.9724	97.24%
CYP2C19 inhibition	-	0.9771	97.71%
CYP2D6 inhibition	-	0.9668	96.68%
CYP1A2 inhibition	-	0.9831	98.31%
CYP2C8 inhibition	-	0.9929	99.29%
CYP inhibitory promiscuity	-	0.9800	98.00%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7691	76.91%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8796	87.96%
Skin irritation	-	0.8453	84.53%
Skin corrosion	-	0.9578	95.78%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8037	80.37%
Micronuclear	-	0.7341	73.41%
Hepatotoxicity	-	0.5488	54.88%
skin sensitisation	-	0.9263	92.63%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.7111	71.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.6504	65.04%
Acute Oral Toxicity (c)	IV	0.6078	60.78%
Estrogen receptor binding	-	0.8134	81.34%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.7099	70.99%
Glucocorticoid receptor binding	-	0.6518	65.18%
Aromatase binding	-	0.8712	87.12%
PPAR gamma	-	0.8014	80.14%
Honey bee toxicity	-	0.8673	86.73%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.8955	89.55%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2179	P04062	Beta-glucocerebrosidase	30000 nM	Ki	PMID: 9871687
CHEMBL1293235	P02545	Prelamin-A/C	794.3 nM; 794.3 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.53%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.60%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	80.46%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.44%	91.11%

Plants that contains it

• Arabidopsis thaliana
• Hyacinthoides non-scripta
• Lotus corniculatus
• Pogostemon cablin
• Solanum lycopersicum

Cross-Links

• PubChem: 7027
• NPASS: NPC220922
• ChEMBL: CHEMBL1200829
• LOTUS: LTS0250595
• wikiData: Q114174