Glucuronolactone

Details

• Internal ID: a04e42d0-1503-4511-a726-6b2546e20c7b
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (2R)-2-[(2S,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetaldehyde
• InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h1-5,8-10H/t2-,3+,4-,5+/m0/s1
• InChI Key: UYUXSRADSPPKRZ-SKNVOMKLSA-N
• Popularity: 150 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₈O₆
• Molecular Weight: 176.12 g/mol
• Exact Mass: 176.03208797 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.81
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• glucuronolactone
• D-Glucurono-6,3-lactone
• D-Glucuronolactone
• GLUCUROLACTONE
• D-Glucurone
• Glucurone
• D-Glucuronic acid lactone
• Glucuronosan
• Guronsan
• Glucoxy
• Glucurolactona
• Glucurolactonum
• Glucuronolattone
• Dicurone
• D-Glucofuranuronic acid, gamma-lactone
• Gluronsan
• D-Glucuronic acid, gamma-lactone
• XE4Y3016M9
• (2R)-2-[(2S,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetaldehyde
• CHEBI:18268
• gamma-Lactone of D-glucofuranuronic acid
• NSC-656
• NSC656
• glucuronic acid, gamma-lactone
• (2R)-2-((2S,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxyacetaldehyde
• RefChem:663158
• GlyTouCan:G10736YH
• CHEBI:24301
• DTXCID001476953
• G10736YH
• 251-053-3
• 63-29-6
• DTXCID4021844
• DTXSID501018940
• DTXSID6041844
• D-Glucurono-3,6-lactone
• d(+)-glucurono-3,6-lactone
• Glucurono-6,3-lactone
• Glucuron
• D-Glucuronic acid, g-lactone
• Glucurolactone [INN]
• Glucuronolactone [JAN]
• MFCD00135622
• Glucuronic acid lactone
• D-(+)-Glucurono-3,6-lactone
• (R)-2-((2S,3R,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)-2-hydroxyacetaldehyde
• Reulatt S.S.
• NSC 656
• Glucurolactone (INN)
• Glucuronolactone (JAN)
• D-Glucurono-gamma-lactone
• 6814-06-8
• Glucuronolattone [DCIT]
• gamma-Glukurolakton
• gamma-Glukurolakton [Czech]
• Glucurolactonum [INN-Latin]
• Glucurolactona [INN-Spanish]
• Glucuronic acid-3,6-lactone
• EINECS 251-053-3
• BRN 0083595
• UNII-XE4Y3016M9
• D-Glucuronicacid,g-lactone
• SCHEMBL28793
• 5-18-05-00033 (Beilstein Handbook Reference)
• D-glucuronic acid, |A-lactone
• GLUCUROLACTONE [MART.]
• d-glucuronic acid-gamma-lactone
• orb1310620
• D-Glucuronic acid, |_-lactone
• D-GLUCURONOLACTONE [MI]
• GLUCUROLACTONE [WHO-DD]
• D-Glucuronolactone-1,6-13C2
• D-glucofuranuronate gamma-lactone
• MSK2831
• HY-41982R
• D-Glucuronic acid lactone (Standard)
• AKOS006341990
• EBC-616129
• KS-1361
• MG02804
• MG46713
• D-Glucofurano-6,3-lactone-1,6-13C2
• HY-41982
• SY005604
• CS-0019952
• NS00013683
• C02670
• D-(+)-Glucuronic acid gamma-lactone, >=99%
• D01800
• D70547
• G-3700
• SBI-0654630.0001
• .GAMMA-LACTONE OF D-GLUCOFURANURONIC ACID
• D-Glucofuranuronic acid,gamma-lactone,1,6-13C2
• F033671
• Q28529701
• D-(+)-Glucuronic acid gamma-lactone, analytical standard
• 00CE759F-D1F9-492E-89F7-B7400A34C72D
• (2R)-2-[(2S,3R,4S)-3,4-dihydroxy-5-oxo-tetrahydrofuran-2-yl]-2-hydroxy-acetaldehyde
• D-Glucurono-6,3-lactoneD-Glucuronic Acid LactoneD(+)-Glucurono-3,6-lactoneD-(+)-Glucuronic acid |A-lactone Glucuronolactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4825	48.25%
Caco-2	-	0.9401	94.01%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6346	63.46%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.9487	94.87%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9802	98.02%
P-glycoprotein inhibitior	-	0.9760	97.60%
P-glycoprotein substrate	-	0.9511	95.11%
CYP3A4 substrate	-	0.6466	64.66%
CYP2C9 substrate	-	0.7936	79.36%
CYP2D6 substrate	-	0.8534	85.34%
CYP3A4 inhibition	-	0.9243	92.43%
CYP2C9 inhibition	-	0.9591	95.91%
CYP2C19 inhibition	-	0.9504	95.04%
CYP2D6 inhibition	-	0.9620	96.20%
CYP1A2 inhibition	-	0.8939	89.39%
CYP2C8 inhibition	-	0.9824	98.24%
CYP inhibitory promiscuity	-	0.9755	97.55%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.6824	68.24%
Eye corrosion	-	0.9427	94.27%
Eye irritation	-	0.7674	76.74%
Skin irritation	-	0.5384	53.84%
Skin corrosion	-	0.7942	79.42%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8561	85.61%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9097	90.97%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.5201	52.01%
Acute Oral Toxicity (c)	IV	0.6143	61.43%
Estrogen receptor binding	-	0.6569	65.69%
Androgen receptor binding	-	0.8878	88.78%
Thyroid receptor binding	-	0.6227	62.27%
Glucocorticoid receptor binding	-	0.6028	60.28%
Aromatase binding	-	0.8043	80.43%
PPAR gamma	-	0.7924	79.24%
Honey bee toxicity	-	0.7843	78.43%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	-	0.5280	52.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.78%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.13%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.25%	89.00%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 92283
• LOTUS: LTS0076652
• wikiData: Q28529701