Melezitose

Details

• Internal ID: 34c870b1-5954-4728-a1c4-05dd046194a7
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C(C1C(C(C(C(O1)OC2C(C(OC2(CO)OC3C(C(C(C(O3)CO)O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-15-10(25)7(3-21)33-18(15,4-22)34-17-14(29)12(27)9(24)6(2-20)31-17/h5-17,19-29H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+/m1/s1
• InChI Key: QWIZNVHXZXRPDR-WSCXOGSTSA-N
• Popularity: 1,742 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₂O₁₆
• Molecular Weight: 504.40 g/mol
• Exact Mass: 504.16903493 g/mol
• Topological Polar Surface Area (TPSA): 269.00 Ų
• XlogP: -5.80
• Atomic LogP (AlogP): -7.57
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

• 597-12-6
• D-Melezitose
• (+)-Melezitose
• CHEBI:6731
• T4T25QN29L
• DTXSID20883458
• NSC-2080
• (2R,3R,4S,5S,6R)-2-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-{[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• alpha-D-Glucopyranoside, O-alpha-D-glucopyranosyl-(1->3)-beta-D-fructofuranosyl
• (2R,3R,4S,5S,6R)-2-(((2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxolan-3-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-((2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxolan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• RefChem:156333
• GlyTouCan:G80689JY
• DTXCID401022988
• G80689JY
• O alpha-D-glucopyranosyl-(1,3)-O beta-D-fructofuranosyl-(2,1) alpha-D-glucopyranoside
• 209-894-9
• D-(+)-Melezitose
• Melizitose
• MFCD00006627
• (+)-Melezitose;D-Melezitose
• Melicitose
• NSC 2080
• (2R,3R,4S,5S,6R)-2-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydrofuran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• UNII-T4T25QN29L
• .alpha.-D-Glucopyranoside, O-.alpha.-D-glucopyranosyl-(1->3)-.beta.-D-fructofuranosyl
• EINECS 209-894-9
• MELEZITOSE [MI]
• AI3-19426
• MELEZITOSE, (+)-
• SCHEMBL131977
• CHEMBL386007
• MSK3231W
• orb1707998
• QWIZNVHXZXRPDR-WSCXOGSTSA-N
• HY-N2340
• s5142
• AKOS015955765
• CCG-269726
• CS-6328
• AS-56726
• DA-65327
• M0049
• NS00014989
• C08243
• C75789
• Q418842
• 58079E13-F3CD-4185-B028-4BD36A97D4D3
• .alpha.-D-Glucopyranoside, O-.alpha.-D-glucopyranosyl-(1-3)-.beta.-D-fructofuranosyl-
• alpha-D-Glucopyranoside, O-alpha-D-glucopyranosyl-(1.fwdarw.3)-beta-D-fructofuranosyl
• alpha-D-glucopyranosyl-(1->3)-beta-D-fructofuranosyl alpha-D-glucopyranoside
• O-alpha-D-glucopyranosyl-(1,3)-beta-D-fructofuranosyl-alpha-D-glucopyranoside
• O-alpha-D-glucopyranosyl-(1-3)-beta-D-fructofuranosyl-alpha-D-glucopyranoside
• (2R,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-6,6'-(((2S,3S,4R,5R)-4-Hydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2,3-diyl)bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)
• O-.ALPHA.-D-GLUCOPYRANOSYL-(1->3)-.BETA.-D-FRUCTOFURANOSYL-.ALPHA.-D-GLUCOPYRANOSIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9685	96.85%
Caco-2	-	0.9082	90.82%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7796	77.96%
OATP2B1 inhibitior	-	0.8640	86.40%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8496	84.96%
P-glycoprotein inhibitior	-	0.8023	80.23%
P-glycoprotein substrate	-	0.9536	95.36%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8378	83.78%
CYP3A4 inhibition	-	0.9410	94.10%
CYP2C9 inhibition	-	0.9095	90.95%
CYP2C19 inhibition	-	0.8373	83.73%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	-	0.9418	94.18%
CYP2C8 inhibition	-	0.8322	83.22%
CYP inhibitory promiscuity	-	0.8369	83.69%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6497	64.97%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9378	93.78%
Skin irritation	-	0.8917	89.17%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7087	70.87%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.9425	94.25%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.5669	56.69%
Acute Oral Toxicity (c)	IV	0.5888	58.88%
Estrogen receptor binding	-	0.5642	56.42%
Androgen receptor binding	-	0.4939	49.39%
Thyroid receptor binding	+	0.6095	60.95%
Glucocorticoid receptor binding	-	0.6434	64.34%
Aromatase binding	+	0.8276	82.76%
PPAR gamma	+	0.5630	56.30%
Honey bee toxicity	-	0.5873	58.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.7319	73.19%

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	93.63%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.10%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.44%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.04%	95.83%
CHEMBL3589	P55263	Adenosine kinase	84.54%	98.05%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.10%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	82.80%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.33%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.70%	85.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.28%	91.24%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	80.74%	95.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.59%	96.21%

Plants that contains it

• Arabidopsis thaliana
• Pogostemon cablin

Cross-Links

• PubChem: 92817
• NPASS: NPC290179
• LOTUS: LTS0145769
• wikiData: Q418842