Sucrose octaacetate

Details

• Internal ID: 9a712684-27d7-4570-af7d-3156816849e7
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2,5-bis(acetyloxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H38O19/c1-12(29)37-9-20-22(40-15(4)32)24(42-17(6)34)25(43-18(7)35)27(45-20)47-28(11-39-14(3)31)26(44-19(8)36)23(41-16(5)33)21(46-28)10-38-13(2)30/h20-27H,9-11H2,1-8H3/t20-,21-,22-,23-,24+,25-,26+,27-,28+/m1/s1
• InChI Key: ZIJKGAXBCRWEOL-SAXBRCJISA-N
• Popularity: 228 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.60 g/mol
• Exact Mass: 678.20072898 g/mol
• Topological Polar Surface Area (TPSA): 238.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.83
• H-Bond Acceptor: 19
• H-Bond Donor: 0
• Rotatable Bonds: 13

Synonyms

• 126-14-7
• Octaacetylsucrose
• FEMA No. 3038
• D-(+)-Sucrose octaacetate
• sucrose octa-acetate
• alpha-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-beta-D-fructofuranosyl, 2,3,4,6-tetraacetate
• Sucrose octaacetate [NF]
• D-(+)-Saccharose Octaacetate
• DTXSID3042423
• NSC-1695
• Octa-O-acetyl D-(+)-Sucrose
• NCGC00160615-01
• 07V591057T
• Sucrose octaacetate (NF)
• (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Octa-O-acetylsucrose
• DTXCID1022423
• MFCD00006623
• a-D-Glucopyranoside,1,3,4,6-tetra-O-acetyl-b-D-fructofuranosyl, 2,3,4,6-tetraacetate
• CAS-126-14-7
• NSC 1695
• EINECS 204-772-1
• BRN 0079290
• AI3-00071
• sucrose-octaacetate
• UNII-07V591057T
• 2,3,4,6,1',3',4',6'-Octa-O-acetylsucrose
• 1,3,4,6-Tetra-O-acetyl-beta-D-fructofuranosyl-alpha-D-glucopyranoside tetraacetate
• SCHEMBL48906
• 5-17-08-00410 (Beilstein Handbook Reference)
• CHEMBL2105790
• SUCROSE OCTAACETATE [MI]
• CHEBI:180783
• Octa-O-acetyl D-(+)-Saccharose
• ZIJKGAXBCRWEOL-SAXBRCJISA-N
• SUCROSE OCTAACETATE [FHFI]
• SUCROSE OCTAACETATE [INCI]
• Sucrose octaacetate, >=97%, FG
• D-(+)-Sucrose octaacetate, 98%
• Tox21_111938
• Tox21_300386
• SUCROSE OCTAACETATE [USP-RS]
• SUCROSE OCTA-ACETATE [MART.]
• AKOS015895274
• SUCROSE OCTA-ACETATE [WHO-DD]
• Tox21_111938_1
• 1,3,4,6-Tetra-O-acetyl-beta-D-fructofuranosyl-alpha-D-glucopyrano- side tetraacetate
• alpha-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-beta-D-fructofuranosyl, tetracetate
• NCGC00160615-02
• NCGC00160615-03
• NCGC00254310-01
• [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2,5-bis(acetyloxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl acetate
• BS-15102
• HY-119309
• CS-0066987
• S0052
• D-(+)-Sucrose octaacetate, analytical standard
• D05935
• F20296
• Q410482
• SR-01000883711
• Q-201753
• SR-01000883711-1
• Sucrose octaacetate, United States Pharmacopeia (USP) Reference Standard
• (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((2S,3S,4R,5R)-3,4-diacetoxy-2,5-bis(acetoxymethyl)tetrahydrofuran-2-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8076	80.76%
Caco-2	-	0.7991	79.91%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8347	83.47%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.8623	86.23%
OATP1B3 inhibitior	+	0.9206	92.06%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9292	92.92%
P-glycoprotein inhibitior	+	0.8433	84.33%
P-glycoprotein substrate	-	0.9388	93.88%
CYP3A4 substrate	+	0.6065	60.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9023	90.23%
CYP3A4 inhibition	-	0.9518	95.18%
CYP2C9 inhibition	-	0.9610	96.10%
CYP2C19 inhibition	-	0.8688	86.88%
CYP2D6 inhibition	-	0.9407	94.07%
CYP1A2 inhibition	-	0.8900	89.00%
CYP2C8 inhibition	-	0.6981	69.81%
CYP inhibitory promiscuity	-	0.8856	88.56%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6495	64.95%
Eye corrosion	-	0.9520	95.20%
Eye irritation	-	0.8697	86.97%
Skin irritation	-	0.8391	83.91%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4855	48.55%
Micronuclear	-	0.6826	68.26%
Hepatotoxicity	-	0.6765	67.65%
skin sensitisation	-	0.8393	83.93%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.7124	71.24%
Acute Oral Toxicity (c)	III	0.8030	80.30%
Estrogen receptor binding	+	0.8318	83.18%
Androgen receptor binding	+	0.5690	56.90%
Thyroid receptor binding	+	0.5999	59.99%
Glucocorticoid receptor binding	+	0.7381	73.81%
Aromatase binding	+	0.6339	63.39%
PPAR gamma	+	0.7266	72.66%
Honey bee toxicity	-	0.6471	64.71%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7155	71.55%
Fish aquatic toxicity	+	0.6946	69.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.80%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.72%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.45%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	89.29%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	88.75%	92.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.45%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	87.27%	94.73%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.05%	82.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.62%	94.33%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.41%	83.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.10%	96.95%
CHEMBL4208	P20618	Proteasome component C5	82.04%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.34%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.08%	97.36%
CHEMBL2581	P07339	Cathepsin D	80.61%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.23%	94.80%

Plants that contains it

• Planchonella vitiensis

Cross-Links

• PubChem: 31340
• LOTUS: LTS0047308
• wikiData: Q410482