Raffinose

Details

• Internal ID: 4a8d3ac2-c28f-44eb-96cc-a8eccf36c852
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3(C(C(C(O3)CO)O)O)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]([C@H](O3)CO)O)O)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1
• InChI Key: MUPFEKGTMRGPLJ-ZQSKZDJDSA-N
• Popularity: 12,134 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

• Melitose
• D-Raffinose
• Gossypose
• Melitriose
• d-(+)-Raffinose
• 512-69-6
• 6G-alpha-D-galactosylsucrose
• rafinose
• raflinose
• Raffinose, pure
• NSC 2025
• UNII-N5O3QU595M
• NSC 170228
• N5O3QU595M
• CHEBI:16634
• AI3-19427
• EINECS 208-146-9
• Caryophyllene alcohol acetate
• beta-D-fructofuranosyl alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranoside
• DTXSID8041111
• NSC-2025
• NSC-170228
• Raffinose hydrate
• alpha-D-glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1->6)-
• alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1-6)-
• alpha-D-Galp-(1->6)-alpha-D-Glcp-(1->2)-beta-D-Fruf
• alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranoside
• alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranosyl-(1->2)-beta-D-fructofuranoside
• alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl (1 to 6)-, hydrate
• beta-D-Fructofuranosyl-O-alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranoside
• alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1-6)-, pentahydrate
• delta-Raffinose
• NSC170228
• (2S,3R,4S,5S,6R)-2-(((2R,3R,4S,5R,6R)-6-((2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl)oxy-3,4,5-trihydroxy-oxan-2-yl)methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• RAF
• Raffinose (8CI)
• Melitriose, Raffinose
• delta-(+)-Raffinose
• RAFFINOSE [MI]
• RAFFINOSE [INCI]
• bmse000221
• RAFFINOSE [WHO-DD]
• SCHEMBL33743
• CHEMBL603717
• 6G-alpha-delta-galactosylsucrose
• DTXCID6021111
• O(C1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C3(CO)OC(CO)C(O)C3O
• beta-D-Fructofuranosyl-O-alpha-D-galactopyranosyl-(1?6)alpha-D-glucopyranoside
• HY-N7088
• s5155
• AKOS025393299
• BS-9703
• CCG-269725
• (2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CS-0081719
• R0002
• C00492
• Q410005
• 720EEA6C-2455-46E5-9CFA-A6800C4E0D6F
• alpha-D-Galp-(1->6)-alpha-D-Glcp-(12)-beta-D-Fruf
• alpha-D-Galp-(1->6)-alpha-D-Glcp-(1<->2)-beta-D-Fruf
• .alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-(1->6)-
• alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl (1 to 6)-
• alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1.fwdarw.6)-
• alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1>6)- (9CI)
• O-alp.-D-Galactopyranosyl-(1-->6)-alp.-D-glucopyranosyl-bet.-D-fructofuranoside
• O-alpha-D-Galactopyranosyl(1,6)-O-alpha-D-glucopyranosyl-(1,2)-beta-D-fructofuranoside
• (2R,3R,4S,5S,6R)-2-((2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yloxy)-6-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
• (2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-2,5-bis(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]oxy-3,4,5-tris(oxidanyl)oxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• (2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-dimethylol-tetrahydrofuran-2-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methoxy]-6-methylol-tetrahydropyran-3,4,5-triol
• .BETA.-D-FRUCTOFURANOSYL-O-.ALPHA.-D-GALACTOPYRANOSYL-(1->6)-.ALPHA.-D-GLUCOPYRANOSIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9685	96.85%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7796	77.96%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.9202	92.02%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8576	85.76%
P-glycoprotein inhibitior	-	0.7786	77.86%
P-glycoprotein substrate	-	0.9446	94.46%
CYP3A4 substrate	+	0.5137	51.37%
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	-	0.8004	80.04%
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	-	0.9312	93.12%
Skin irritation	-	0.8917	89.17%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7526	75.26%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.9425	94.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.5831	58.31%
Acute Oral Toxicity (c)	IV	0.5888	58.88%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.6033	60.33%
Thyroid receptor binding	+	0.5938	59.38%
Glucocorticoid receptor binding	-	0.5471	54.71%
Aromatase binding	+	0.8503	85.03%
PPAR gamma	+	0.5354	53.54%
Honey bee toxicity	-	0.7051	70.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	-	0.7319	73.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2094128	P24941	Cyclin-dependent kinase 2/cyclin A	16 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.71%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	90.45%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.21%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.80%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	85.32%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.19%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.75%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.65%	95.83%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.41%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.66%	94.00%

Plants that contains it

• Agave americana
• Allium sativum
• Allium suworowi
• Amaranthus cruentus
• Arabidopsis thaliana
• Cajanus cajan
• Cannabis sativa
• Gentiana lutea
• Glycine max
• Gossypium hirsutum
• Hedera pastuchovii
• Helianthus annuus
• Ilex paraguariensis
• Linum usitatissimum
• Lonicera caerulea
• Lotus corniculatus
• Lotus corniculatus subsp. corniculatus
• Lupinus mutabilis
• Nicotiana tabacum
• Origanum vulgare
• Panax ginseng
• Phaseolus coccineus
• Pogostemon cablin
• Polygonatum sewerzowi
• Populus nigra
• Populus tremula
• Pseudostellaria heterophylla
• Rehmannia glutinosa
• Rosulabryum capillare
• Rubia argyi
• Schinus molle
• Scrophularia nodosa
• Tamarix aphylla
• Teucrium polium
• Trigonella foenum-graecum
• Vigna unguiculata
• Xanthium strumarium

Cross-Links

• PubChem: 439242
• NPASS: NPC34877
• LOTUS: LTS0113066
• wikiData: Q410005