NP-MRD: Showing NP-Card for Raffinose (NP0000023)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:41 UTC

Updated at

2024-09-03 04:18:44 UTC

NP-MRD ID

NP0000023

Natural Product DOI

https://doi.org/10.57994/1496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Raffinose

Description

Raffinose is a complex carbohydrate. It is a trisaccharide composed of galactose, fructose, and glucose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose is hydrolyzed to D-galactose and sucrose by D-galactosidase (D-GAL). D-GAL also hydrolyzes other D-galactosides such as stachyose, verbascose, and galactinol [1-O-(D-galactosyl)-myoinositol], if present. The enzyme does not cleave linked galactose, as in lactose. Raffinose is also known as melitose and may be thought of as galactose and sucrose connected via an alpha(1->6) glycosidic linkage. Thus, raffinose can be broken down into galactose and sucrose via the enzyme alpha-galactosidase. Human intestines do not contain this enzyme. Raffinose is a trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652308122017202D          

 34 36  0  0  0  0            999 V2000
 9999.578210002.6911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.070410000.8327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.279010000.8389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.812310002.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.097810002.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.005410000.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7191 9999.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1484 9997.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8621 9997.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2897 9998.9789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2897 9997.3288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7191 9996.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.005410003.5161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.436910002.6911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.436910001.0410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.919310003.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.659910003.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.192110002.7729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.524710002.2879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.779610001.5033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.604610001.5033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.859510002.2879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.006110002.6911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.291610002.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.291610001.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.006110001.0411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.720610001.4535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.720610002.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7198 9998.9783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0053 9998.5658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0053 9997.7407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7198 9997.3283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4343 9997.7407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4343 9998.5658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 34  1  0  0  0  0
 33 34  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24  1  1  6  0  0  0
 26  6  1  1  0  0  0
 27 15  1  6  0  0  0
 28 14  1  1  0  0  0
 23 13  1  6  0  0  0
 29  7  1  1  0  0  0
 33  8  1  6  0  0  0
 32 12  1  6  0  0  0
 31 11  1  6  0  0  0
 30 10  1  1  0  0  0
  1 22  1  0  0  0  0
 22 16  1  6  0  0  0
 19  4  1  1  0  0  0
 20  3  1  6  0  0  0
 21  2  1  1  0  0  0
M  END


  Mrv1652308122017202D          

 34 36  0  0  0  0            999 V2000
 9999.578210002.6911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.070410000.8327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.279010000.8389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.812310002.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.097810002.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.005410000.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7191 9999.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1484 9997.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8621 9997.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2897 9998.9789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2897 9997.3288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7191 9996.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.005410003.5161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.436910002.6911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.436910001.0410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.919310003.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.659910003.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.192110002.7729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.524710002.2879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.779610001.5033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.604610001.5033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.859510002.2879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.006110002.6911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.291610002.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.291610001.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.006110001.0411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.720610001.4535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.720610002.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7198 9998.9783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0053 9998.5658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0053 9997.7407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7198 9997.3283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4343 9997.7407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4343 9998.5658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 34  1  0  0  0  0
 33 34  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24  1  1  6  0  0  0
 26  6  1  1  0  0  0
 27 15  1  6  0  0  0
 28 14  1  1  0  0  0
 23 13  1  6  0  0  0
 29  7  1  1  0  0  0
 33  8  1  6  0  0  0
 32 12  1  6  0  0  0
 31 11  1  6  0  0  0
 30 10  1  1  0  0  0
  1 22  1  0  0  0  0
 22 16  1  6  0  0  0
 19  4  1  1  0  0  0
 20  3  1  6  0  0  0
 21  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0000023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C18H32O16

> <MOLECULAR_WEIGHT>
504.4371

> <EXACT_MASS>
504.169034976

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.17173301178494

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
-3.36

> <JCHEM_LOGP>
-6.299670609333333

> <ALOGPS_LOGS>
0.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.148641922410812

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.695274801560533

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483773177512537

> <JCHEM_POLAR_SURFACE_AREA>
268.67999999999995

> <JCHEM_REFRACTIVITY>
101.18739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.69e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
raffinose

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  O   UNK     0    8665.8798671.690   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8664.9318668.221   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8661.5878668.233   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8660.7168671.690   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8659.3838670.920   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8668.5438667.070   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8669.8768666.301   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8672.5448661.680   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8673.8768662.449   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8667.2078664.761   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8667.2078661.680   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8669.8768660.140   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8668.5438673.230   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8671.2168671.690   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8671.2168668.610   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8664.6498672.457   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8666.0328673.135   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8663.2928671.843   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8662.0468670.937   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8662.5228669.473   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.0628669.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8664.5388670.937   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.5458671.690   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.2118670.920   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8667.2118669.380   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0    8668.5458668.610   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8669.8788669.380   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8669.8788670.920   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8669.8778664.759   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8668.5438663.989   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8668.5438662.449   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8669.8778661.679   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8671.2118662.449   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0    8671.2118663.989   0.000  0.00  0.00           O+0
CONECT    1   24   22                                                       
CONECT    2   21                                                            
CONECT    3   20                                                            
CONECT    4    5   19                                                       
CONECT    5    4                                                            
CONECT    6    7   26                                                       
CONECT    7    6   29                                                       
CONECT    8    9   33                                                       
CONECT    9    8                                                            
CONECT   10   30                                                            
CONECT   11   31                                                            
CONECT   12   32                                                            
CONECT   13   23                                                            
CONECT   14   28                                                            
CONECT   15   27                                                            
CONECT   16   17   22                                                       
CONECT   17   16                                                            
CONECT   18   19   22                                                       
CONECT   19   20   18    4                                                  
CONECT   20   19   21    3                                                  
CONECT   21   20   22    2                                                  
CONECT   22   21   18    1   16                                             
CONECT   23   24   28   13                                                  
CONECT   24   23   25    1                                                  
CONECT   25   24   26                                                       
CONECT   26   27   25    6                                                  
CONECT   27   26   28   15                                                  
CONECT   28   23   27   14                                                  
CONECT   29   30   34    7                                                  
CONECT   30   29   31   10                                                  
CONECT   31   30   32   11                                                  
CONECT   32   31   33   12                                                  
CONECT   33   32   34    8                                                  
CONECT   34   29   33                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
6g-alpha-D-Galactosylsucrose	ChEBI
alpha-D-Galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranoside	ChEBI
alpha-D-Galp-(1->6)-alpha-D-GLCP-(12)-beta-D-fruf	ChEBI
Gossypose	ChEBI
Melitose	ChEBI
Melitriose	ChEBI
Rafinose	ChEBI
Raflinose	ChEBI
6g-a-D-Galactosylsucrose	Generator
6g-Α-D-galactosylsucrose	Generator
a-D-Galactopyranosyl-(1->6)-a-D-glucopyranosyl b-D-fructofuranoside	Generator
Α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl β-D-fructofuranoside	Generator
a-D-Galp-(1->6)-a-D-GLCP-(12)-b-D-fruf	Generator
Α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-fruf	Generator
D-(+)-Raffinose	HMDB
D-Raffinose	HMDB
beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1→6)-alpha-D-glucopyranoside	HMDB
Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside	HMDB
Raffinose	HMDB

Chemical Formula

C₁₈H₃₂O₁₆

Average Mass

504.4371 Da

Monoisotopic Mass

504.16903 Da

IUPAC Name

(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

Traditional Name

raffinose

CAS Registry Number

512-69-6

SMILES

[H][C@]1(CO)O[C@@](CO)(O[C@@]2([H])O[C@]([H])(CO[C@@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, C2D6OS, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus		FooDB
Actinidia chinensis		FooDB
Agaricus bisporus		FooDB
Agave		FooDB
Agave americana		LOTUS database
Allium ampeloprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium ascalonicum		FooDB
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium cepa L.		FooDB
Allium fistulosum		FooDB
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium schoenoprasum		FooDB
Allium suworowii		LOTUS database
Allium tuberosum		FooDB
Aloysia triphylla		FooDB
Amaranthus		FooDB
Amelanchier alnifolia		FooDB
Anacardium occidentale		FooDB
Ananas comosus		FooDB
Anethum graveolens		FooDB
Angelica keiskei		FooDB
Annona cherimola		FooDB
Annona muricata		FooDB
Annona reticulata		FooDB
Annona squamosa		FooDB
Anthriscus cerefolium		FooDB
Apium graveolens		FooDB
Apium graveolens var. dulce		FooDB
Apium graveolens var. rapaceum		FooDB
Apium graveolens var. secalinum		FooDB
Arabidopsis thaliana	Plant	KNApSAcK
Arachis hypogaea		FooDB
Arctium lappa		FooDB
Armoracia rusticana		FooDB
Artemisia dracunculus		FooDB
Artemisia vulgaris		FooDB
Artocarpus altilis		FooDB
Artocarpus heterophyllus		FooDB
Asparagus officinalis		FooDB
Attalea speciosa		FooDB
Auricularia auricula-judae		FooDB
Auricularia polytricha		FooDB
Avena sativa L.		FooDB
Averrhoa carambola		FooDB
Basella alba		FooDB
Benincasa hispida		FooDB
Bertholletia excelsa		FooDB
Beta vulgaris		FooDB
Beta vulgaris ssp. cicla		FooDB
Borago officinalis		FooDB
Brassica alboglabra		FooDB
Brassica juncea		FooDB
Brassica napus		FooDB
Brassica napus var. napus		FooDB
Brassica oleracea		FooDB
Brassica oleracea L. ssp. Botrytis	Plant	KNApSAcK
Brassica oleracea var. botrytis		FooDB
Brassica oleracea var. capitata		FooDB
Brassica oleracea var. gemmifera		FooDB
Brassica oleracea var. gongylodes		FooDB
Brassica oleracea var. italica		FooDB
Brassica oleracea var. sabauda		FooDB
Brassica oleracea var. viridis		FooDB
Brassica rapa		FooDB
Brassica rapa ssp. chinensis		FooDB
Brassica rapa var. pekinensis		FooDB
Brassica rapa var. rapa		FooDB
Brassica ruvo		FooDB
Brosimum alicastrum		FooDB
Bryum capillare		LOTUS database
Byrsonima crassifolia		FooDB
Cajanus cajan		FooDB
Canarium ovatum		FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius		FooDB
Capparis spinosa		FooDB
Capsicum annuum		FooDB
Capsicum annuum L.		FooDB
Capsicum annuum var. annuum		FooDB
Capsicum chinense		FooDB
Capsicum pubescens		FooDB
Carica papaya L.	Plant	KNApSAcK
Carissa macrocarpa		FooDB
Carthamus tinctorius		FooDB
Carum carvi		FooDB
Carya		FooDB
Carya illinoinensis		FooDB
Castanea		FooDB
Castanea crenata		FooDB
Castanea mollissima		FooDB
Castanea sativa		FooDB
Ceratonia siliqua	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chamaemelum nobile		FooDB
Chamerion angustifolium		FooDB
Chenopodium album		FooDB
Chenopodium quinoa		FooDB
Chrysanthemum coronarium		FooDB
Cicer arietinum		FooDB
Cichorium endivia		FooDB
Cichorium intybus		FooDB
Cinara laricis		LOTUS database
Cinnamomum		FooDB
Cinnamomum aromaticum		FooDB
Cinnamomum verum		FooDB
Cirsium		FooDB
Citrullus lanatus		FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)		FooDB
Citrus aurantiifolia		FooDB
Citrus latifolia		FooDB
Citrus limon		FooDB
Citrus maxima		FooDB
Citrus paradisi		FooDB
Citrus reticulata		FooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)		FooDB
Cocos nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea canephora		FooDB
Colocasia esculenta		FooDB
Corchorus olitorius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coriandrum sativum L.		FooDB
Corylus		FooDB
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Crateva religiosa		FooDB
Crocus sativus		FooDB
Cucumis melo		FooDB
Cucumis metuliferus		FooDB
Cucumis sativus L.		FooDB
Cucurbita		FooDB
Cucurbita maxima		FooDB
Cucurbita moschata		FooDB
Cuminum cyminum		FooDB
Curcuma longa		FooDB
Cydonia oblonga		FooDB
Cymbopogon citratus		FooDB
Cynara cardunculus		FooDB
Cynara scolymus		FooDB
Daphnia pulex		LOTUS database
Daucus carota		FooDB
Daucus carota ssp. sativus		FooDB
Dimocarpus longan		FooDB
Dioscorea		FooDB
Dioscorea pentaphylla		FooDB
Diospyros		FooDB
Diospyros kaki		FooDB
Diospyros virginiana		FooDB
Durio zibethinus		FooDB
Dysphania ambrosioides		FooDB
Elaeis		FooDB
Eleocharis dulcis		FooDB
Elettaria cardamomum		FooDB
Empetrum nigrum		FooDB
Eragrostis tef		FooDB
Eriobotrya japonica		FooDB
Eruca vesicaria subsp. Sativa		FooDB
Eugenia javanica		FooDB
Eugenia uniflora		FooDB
Eutrema japonicum		FooDB
Fagopyrum esculentum		FooDB
Fagopyrum tataricum		FooDB
Fagus		FooDB
Feijoa sellowiana		FooDB
Ficus carica		FooDB
Flammulina velutipes		FooDB
Foeniculum vulgare		FooDB
Fragaria x ananassa		FooDB
Garcinia mangostana		FooDB
Gaylussacia baccata		FooDB
Gentiana lutea	Plant	KNApSAcK
Gentiana spp.	Plant	KNApSAcK
Gentiana straminea	Plant	KNApSAcK
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium hirsutum		LOTUS database
Grifola frondosa		FooDB
Hedera pastuchowii		LOTUS database
Hedysarum alpinum		FooDB
Helianthus annuus		LOTUS database
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus tuberosus		FooDB
Hibiscus sabbariffa		FooDB
Hippophae rhamnoides		FooDB
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hyssopus officinalis L.		FooDB
Ilex paraguariensis		LOTUS database
Illicium verum		FooDB
Ipomoea aquatica		FooDB
Ipomoea batatas		FooDB
Juglans		FooDB
Juglans ailanthifolia		FooDB
Juglans cinerea		FooDB
Juglans nigra L.		FooDB
Juglans regia		FooDB
Lablab purpureus		FooDB
Lactuca sativa		FooDB
Lagenaria siceraria		FooDB
Lathyrus sativus		FooDB
Laurus nobilis L.		FooDB
Lens culinaris		FooDB
Lentinus edodes		FooDB
Lepidium sativum		FooDB
Levisticum officinale		FooDB
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Litchi chinensis		FooDB
Lonicera caerulea		LOTUS database
Lotus corniculatus		LOTUS database
Lotus glaber		LOTUS database
Luffa aegyptiaca		FooDB
Lupinus		FooDB
Lupinus albus		FooDB
Lupinus mutabilis		LOTUS database
Macadamia		FooDB
Macadamia tetraphylla		FooDB
Malpighia emarginata		FooDB
Malus		FooDB
Malus pumila		FooDB
Mammea americana		FooDB
Mangifera indica		FooDB
Manihot esculenta		FooDB
Manilkara zapota		FooDB
Maranta arundinacea		FooDB
Matricaria recutita		FooDB
Matteuccia struthiopteris		FooDB
Medicago sativa		FooDB
Melissa officinalis L.		FooDB
Mentha		FooDB
Mentha aquatica		FooDB
Mentha arvensis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha spicata		FooDB
Mentha x piperita		FooDB
Mespilus germanica		FooDB
Metroxylon sagu		FooDB
Momordica charantia		FooDB
Morchellaceae		FooDB
Morella rubra		FooDB
Moringa oleifera		FooDB
Morus		FooDB
Morus nigra		FooDB
Mus musculus		LOTUS database
Musa acuminata		FooDB
Musa x paradisiaca		FooDB
Myrica		FooDB
Myristica fragrans		FooDB
Nelumbo		FooDB
Nelumbo nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nephelium lappaceum		FooDB
Nicotiana tabacum		LOTUS database
Nuphar lutea		FooDB
Ocimum basilicum		FooDB
Oenothera biennis		FooDB
Olea europaea		FooDB
Opuntia		FooDB
Opuntia cochenillifera		FooDB
Opuntia macrorhiza		FooDB
Origanum majorana		FooDB
Origanum onites		FooDB
Origanum vulgare		FooDB
Origanum X majoricum		FooDB
Oryza rufipogon		FooDB
Oryza sativa		FooDB
Pachyrhizus erosus		FooDB
Panax ginseng	Plant	KNApSAcK
Pangium edule		FooDB
Panicum miliaceum		FooDB
Passiflora edulis		FooDB
Pastinaca sativa		FooDB
Pediomelum esculentum		FooDB
Perideridia oregana		FooDB
Persea americana		FooDB
Petasites japonicus		FooDB
Petroselinum crispum		FooDB
Phaseolus coccineus		FooDB
Phaseolus lunatus		FooDB
Phaseolus vulgaris		FooDB
Phoenix dactylifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Photinia melanocarpa		FooDB
Phyllostachys edulis		FooDB
Physalis		FooDB
Physalis philadelphica var. immaculata		FooDB
Phytolacca americana		FooDB
Pimenta dioica		FooDB
Pimpinella anisum		FooDB
Pinus		FooDB
Pinus edulis		FooDB
Piper nigrum L.		FooDB
Pistacia vera		FooDB
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Plantago asiatica	Plant	KNApSAcK
Pleiogynium timoriense		LOTUS database
Pleurotus ostreatus		FooDB
Polygonum alpinum		FooDB
Populus maximowiczii		LOTUS database
Populus tremula		LOTUS database
Portulaca oleracea		FooDB
Pouteria sapota		FooDB
Prunus armeniaca		FooDB
Prunus avium	Plant	KNApSAcK
Prunus avium L.		FooDB
Prunus cerasus		FooDB
Prunus domestica		FooDB
Prunus dulcis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica		FooDB
Prunus persica var. nucipersica		FooDB
Prunus persica var. persica		FooDB
Prunus tomentosa		FooDB
Prunus virginiana		FooDB
Pseudostellaria heterophylla		LOTUS database
Psidium cattleianum		FooDB
Psidium guajava		FooDB
Psophocarpus tetragonolobus		FooDB
Punica granatum		FooDB
Pyrus communis		FooDB
Pyrus pyrifolia		FooDB
Quercus		FooDB
Raphanus sativus		FooDB
Raphanus sativus var. longipinnatus		FooDB
Raphanus sativus var. sativus		FooDB
Rehmannia glutinosa	Plant	KNApSAcK
Rheum rhabarbarum		FooDB
Ribes aureum		FooDB
Ribes glandulosum		FooDB
Ribes nigrum		FooDB
Ribes rubrum		FooDB
Ribes uva-crispa		FooDB
Rosa		FooDB
Rubus arcticus		FooDB
Rubus chamaemorus		FooDB
Rubus idaeus		FooDB
Rubus occidentalis		FooDB
Rubus spectabilis		FooDB
Rumex		FooDB
Rumex acetosa		FooDB
Rumex articus		FooDB
Sagittaria latifolia		FooDB
Salacia oblonga		LOTUS database
Salix pulchra		FooDB
Salvia elegans		FooDB
Salvia hispanica		FooDB
Salvia officinalis		FooDB
Salvia rosmarinus		FooDB
Sambucus nigra		FooDB
Sambucus nigra L.		FooDB
Satureja hortensis L.		FooDB
Satureja montana		FooDB
Scorzonera hispanica		FooDB
Scrophularia nodosa		LOTUS database
Secale cereale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sechium edule		FooDB
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesbania bispinosa		FooDB
Sinapis alba		FooDB
Sisymbrium		FooDB
Solanum lycopersicum		FooDB
Solanum lycopersicum var. cerasiforme		FooDB
Solanum lycopersicum var. lycopersicum		FooDB
Solanum melongena		FooDB
Solanum quitoense		FooDB
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sorbus aucuparia		FooDB
Sorghum bicolor		FooDB
Sphenostylis stenocarpa		LOTUS database
Spinacia oleracea		FooDB
Syzygium aromaticum		FooDB
Syzygium cumini	Plant	KNApSAcK
Syzygium jambos		FooDB
Tamarindus indica		FooDB
Tamarix aphylla		LOTUS database
Taraxacum officinale		FooDB
Taxus baccata	Plant	KNApSAcK
Tetragonia tetragonioides		FooDB
Teucrium polium		LOTUS database
Thelesperma		FooDB
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Thymus pulegioides		FooDB
Thymus vulgaris		FooDB
Tilia cordata		FooDB
Tilia L.		FooDB
Tragopogon porrifolius		FooDB
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum		FooDB
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum durum		FooDB
Triticum spelta		FooDB
Triticum turanicum		FooDB
Typha angustifolia		FooDB
Vaccinium		FooDB
Vaccinium angustifolium		FooDB
Vaccinium angustifolium X Vaccinium corymbosum		FooDB
Vaccinium arboreum		FooDB
Vaccinium corymbosum		FooDB
Vaccinium deliciosum		FooDB
Vaccinium elliottii		FooDB
Vaccinium macrocarpon		FooDB
Vaccinium myrtilloides		FooDB
Vaccinium myrtillus		FooDB
Vaccinium ovalifolium		FooDB
Vaccinium ovatum		FooDB
Vaccinium oxycoccos		FooDB
Vaccinium parvifolium		FooDB
Vaccinium reticulatum		FooDB
Vaccinium stamineum		FooDB
Vaccinium uliginosum		FooDB
Vaccinium vitis-idaea		FooDB
Valerianella locusta		FooDB
Vanilla		FooDB
Verbena officinalis		FooDB
Viburnum edule		FooDB
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna aconitifolia		FooDB
Vigna angularis		FooDB
Vigna mungo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna umbellata		FooDB
Vigna unguiculata		FooDB
Vigna unguiculata ssp. cylindrica		FooDB
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna unguiculata var. sesquipedalis		FooDB
Vitis		FooDB
Vitis aestivalis		FooDB
Vitis labrusca		FooDB
Vitis rotundifolia		FooDB
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Xanthosoma sagittifolium		FooDB
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zizania		FooDB
Zizania aquatica		FooDB
Ziziphus zizyphus		FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Tetrahydrofuran
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

trisaccharide (CHEBI:16634 )
raffinose family oligosaccharide (CHEBI:16634 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	80 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	203 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	669 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-6.3	ChemAxon
logS	0.12	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	268.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	101.19 m³·mol⁻¹	ChemAxon
Polarizability	46.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0003213

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001145

Chemspider ID

Not Available

KEGG Compound ID

C00492

BioCyc ID

CPD-1099

BiGG ID

Not Available

Wikipedia Link

Raffinose

METLIN ID

Not Available

PubChem Compound

439242

PDB ID

Not Available

ChEBI ID

16634

Good Scents ID

Not Available

References

General References

Rodrigues Silva C, Dutra de Oliveira JE, de Souza RA, Silva HC: Effect of a rice bran fiber diet on serum glucose levels of diabetic patients in Brazil. Arch Latinoam Nutr. 2005 Mar;55(1):23-7. [PubMed:16187674 ]
Lobley RW, Burrows PC, Warwick R, Dawson DJ, Holmes R: Simultaneous assessment of intestinal permeability and lactose tolerance with orally administered raffinose, lactose and L-arabinose. Clin Sci (Lond). 1990 Aug;79(2):175-83. [PubMed:2167807 ]
Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60. [PubMed:1176592 ]
Toussaint M, Latger-Cannard V, Caron A, Lecompte T, Vigneron C, Menu P: Hemoglobin-based oxygen carriers do not alter platelet functions: study of three chemically modified hemoglobin solutions. Intensive Care Med. 2003 Jan;29(1):62-8. Epub 2002 Nov 30. [PubMed:12528024 ]
Xue S, Paterson W, Valdez D, Miller D, Christoff B, Wong LT, Diamant NE: Effect of an o-raffinose cross-linked haemoglobin product on oesophageal and lower oesophageal sphincter motor function. Neurogastroenterol Motil. 1999 Dec;11(6):421-30. [PubMed:10583849 ]
Persson AE, Schnermann J, Agerup B, Eriksson NE: The hydraulic conductivity of the rat proximal tubular wall determined with colloidal solutions. Pflugers Arch. 1975 Oct 16;360(1):25-44. [PubMed:1237863 ]
Hessels J, Snoeyink EJ, Platenkamp AJ, Voortman G, Steggink J, Eidhof HH: Assessment of intestinal permeability: enzymatic determination of urinary mannitol, raffinose, sucrose and lactose on Hitachi analyzer. Clin Chem Lab Med. 2003 Jan;41(1):33-8. [PubMed:12636047 ]
Horodniceanu T, Delbos F: [Group D streptococci in human infections: identification and sensitivity to antibiotics (author's transl)]. Ann Microbiol (Paris). 1980 Sep-Oct;131B(2):131-44. [PubMed:7458116 ]
Lieberthal W, Fuhro R, Alam H, Rhee P, Szebeni J, Hechtman HB, Favuzza J, Veech RL, Valeri CR: Comparison of the effects of a 50% exchange-transfusion with albumin, hetastarch, and modified hemoglobin solutions. Shock. 2002 Jan;17(1):61-9. [PubMed:11795671 ]
Gundermann KJ, Lie TS: Problems of competition in charcoal hemoperfusion for the treatment of intoxications. Artif Organs. 1979 Nov;3(4):346-9. [PubMed:533425 ]

Showing NP-Card for Raffinose (NP0000023)

MOL for NP0000023 (Raffinose)

3D MOL for NP0000023 (Raffinose)

3D SDF for NP0000023 (Raffinose)

3D-SDF for NP0000023 (Raffinose)

PDB for NP0000023 (Raffinose)

3D PDB for NP0000023 (Raffinose)

SMILES for NP0000023 (Raffinose)

INCHI for NP0000023 (Raffinose)

Structure for NP0000023 (Raffinose)

3D Structure for NP0000023 (Raffinose)