Levoglucosan

Details

• Internal ID: 166dd8a5-1bf1-4b36-ba11-2be845065ec1
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• SMILES (Canonical): C1C2C(C(C(C(O1)O2)O)O)O
• SMILES (Isomeric): C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)O)O)O
• InChI: InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1
• InChI Key: TWNIBLMWSKIRAT-VFUOTHLCSA-N
• Popularity: 448 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14 g/mol
• Exact Mass: 162.05282342 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.18
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 498-07-7
• 1,6-Anhydro-beta-D-glucopyranose
• Leucoglucosan
• 1,6-Anhydro-beta-D-glucose
• 1,6-Anhydro-beta-glucopyranose
• 1,6-Anhydroglucose
• Glucosan
• (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• 1,6-Anhydro-D-glucose
• 1,6-Anhydro-b-D-glucopyranose
• 1,6-Anhydro-b-D-glucose
• CHEBI:30997
• 5132N17FSD
• .beta.-D-Glucopyranose, 1,6-anhydro-
• Anhydro-d-mannosan
• MFCD00063248
• NSC 46243
• 1,6-Anhydro--D-glucose
• UNII-5132N17FSD
• 1,6-Anhydro-D-glucopyranoside
• CCRIS 4273
• L-glucosan
• NSC-46243
• 4PW
• EINECS 207-855-0
• Anhydro-delta-mannosan
• AI3-61731
• bmse000569
• 1,6-Anhydro-delta-glucose
• SCHEMBL195289
• 1,6-Anhydro-beta-delta-glucose
• CHEMBL3138649
• (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (non-preferred name)
• TWNIBLMWSKIRAT-VFUOTHLCSA-N
• D-GLUCOSE, 1,6-ANHYDRO-
• 1,6-Anhydro- beta -D-glucopyranose
• 1,6-Anhydro-beta-D-glucose, 99%
• beta-D-Glucopyranose, 1,6-anhydro-
• GEO-00235
• 1,6-Anhydro-beta-delta-glucopyranose
• AKOS006281170
• AKOS015924837
• CS-W023160
• FS-4431
• HY-W050145
• 1,6-ANHYDRO-D-GLUCOSE [USP-RS]
• A1074
• T70965
• EN300-7375411
• A827859
• Q6535767
• 6,8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.
• Z1198149756
• 6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.
• (1R,2S,3S,4R,5R)-6,8-dioxa-bicyclo[3.2.1]octane-2,3,4-triol
• 1,6-Anhydro-D-glucose, United States Pharmacopeia (USP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7615	76.15%
Caco-2	-	0.9129	91.29%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5950	59.50%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9687	96.87%
OATP1B3 inhibitior	+	0.9597	95.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9685	96.85%
P-glycoprotein inhibitior	-	0.9798	97.98%
P-glycoprotein substrate	-	0.9709	97.09%
CYP3A4 substrate	-	0.6317	63.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8166	81.66%
CYP3A4 inhibition	-	0.9634	96.34%
CYP2C9 inhibition	-	0.9574	95.74%
CYP2C19 inhibition	-	0.9205	92.05%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.9308	93.08%
CYP2C8 inhibition	-	0.9665	96.65%
CYP inhibitory promiscuity	-	0.9732	97.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6413	64.13%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.6258	62.58%
Skin irritation	-	0.8109	81.09%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6900	69.00%
Micronuclear	-	0.6041	60.41%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9280	92.80%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.5570	55.70%
Acute Oral Toxicity (c)	IV	0.4499	44.99%
Estrogen receptor binding	-	0.8835	88.35%
Androgen receptor binding	-	0.8638	86.38%
Thyroid receptor binding	-	0.6984	69.84%
Glucocorticoid receptor binding	-	0.7862	78.62%
Aromatase binding	-	0.8788	87.88%
PPAR gamma	-	0.8278	82.78%
Honey bee toxicity	-	0.7484	74.84%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.8328	83.28%

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	86.85%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.86%	97.21%

Plants that contains it

• Agave americana
• Arabidopsis thaliana
• Harrisonia perforata
• Lotus corniculatus
• Lotus corniculatus subsp. corniculatus

Cross-Links

• PubChem: 2724705
• LOTUS: LTS0255523
• wikiData: Q104938562