NP-MRD: Showing NP-Card for Maltobionic acid (NP0336722)

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Record Information

Version

2.0

Created at

2024-09-11 07:33:40 UTC

Updated at

2024-09-11 07:33:41 UTC

NP-MRD ID

NP0336722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Maltobionic acid

Description

Maltobionic acid is also known as maltobionate. Maltobionic acid was first documented in 2018 (PMID: 35558231). Based on a literature review a significant number of articles have been published on Maltobionic acid (PMID: 38188310) (PMID: 37246400) (PMID: 37058246) (PMID: 36539642) (PMID: 36526877) (PMID: 35959256).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262310052D          

 24 24  0  0  0  0            999 V2000
    2.5171   -1.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8572   -2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -2.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067   -2.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2889   -1.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889    0.1234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712    0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712    1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311    1.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489    2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089    3.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -0.3715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141    0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7742    0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    0.4538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -1.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8667   -2.5175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067    3.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6186   -3.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7742    1.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141   -1.2797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712    1.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4 21  1  0  0  0  0
  5  6  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6 23  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10 24  1  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  2  0  0  0  0
 12 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)C(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)

> <INCHI_KEY>
JYTUSYBCFIZPBE-UHFFFAOYNA-N

> <FORMULA>
C12H22O12

> <MOLECULAR_WEIGHT>
358.296

> <EXACT_MASS>
358.111126148

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
31.66470378465536

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,5,6-tetrahydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanoic acid

> <JCHEM_LOGP>
-5.180579956333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.102947959919355

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.261370489979411

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5247961073479206

> <JCHEM_POLAR_SURFACE_AREA>
217.59999999999997

> <JCHEM_REFRACTIVITY>
70.6843

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
maltobionic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0       4.699  -3.312   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.467  -4.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.080  -3.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.001  -4.391   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.386  -3.774   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.539  -2.234   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.693  -1.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.539   0.230   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.693   1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.693   2.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.925   3.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.771   5.161   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.003   5.931   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.850  -0.693   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.080   0.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.312   1.462   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.699   0.847   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.080  -1.926   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.618  -4.699   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.386   5.931   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.155  -5.931   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.312   3.466   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.080  -2.389   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.693   3.311   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    9   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    3    7                                                       
CONECT   19    5                                                            
CONECT   20   12                                                            
CONECT   21    4                                                            
CONECT   22   11                                                            
CONECT   23    6                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
Maltobionate	Generator

Chemical Formula

C₁₂H₂₂O₁₂

Average Mass

358.2960 Da

Monoisotopic Mass

358.11113 Da

IUPAC Name

2,3,5,6-tetrahydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanoic acid

Traditional Name

maltobionic acid

CAS Registry Number

Not Available

SMILES

OCC(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)C(O)C(O)=O

InChI Identifier

InChI=1/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)

InChI Key

JYTUSYBCFIZPBE-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-5.2	ChemAxon
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	217.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	70.68 m³·mol⁻¹	ChemAxon
Polarizability	31.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

de Souza RC, da Silva LM, Buratti BA, Carra S, Flores M, Puton BM, Rigotti M, Salvador M, Malvessi E, Moreira FKV, Steffens C, Valduga E, Zeni J: Purification, bioactivity and application of maltobionic acid in active films. 3 Biotech. 2024 Jan;14(1):32. doi: 10.1007/s13205-023-03879-3. Epub 2024 Jan 3. [PubMed:38188310 ]
Liu J, Zhang Y, van Dongen K, Kennedy C, Schotman MJG, Marin San Roman PP, Storm C, Dankers PYW, Sijbesma RP: Hepatic Spheroid Formation on Carbohydrate-Functionalized Supramolecular Hydrogels. Biomacromolecules. 2023 Jun 12;24(6):2447-2458. doi: 10.1021/acs.biomac.2c01390. Epub 2023 May 29. [PubMed:37246400 ]
Bieringer E, Garcia Vazquez U, Klein L, Moreto Bravo N, Tobler M, Weuster-Botz D: Bioproduction and applications of aldobionic acids with a focus on maltobionic and cellobionic acid. Bioprocess Biosyst Eng. 2023 Jul;46(7):921-940. doi: 10.1007/s00449-023-02872-7. Epub 2023 Apr 14. [PubMed:37058246 ]
Cho C, Eom GT: Enhanced production of maltobionic acid by a metabolically engineered Escherichia coli incapable of maltose utilization. Bioprocess Biosyst Eng. 2023 Apr;46(4):507-513. doi: 10.1007/s00449-022-02835-4. Epub 2022 Dec 20. [PubMed:36539642 ]
Cho C, Eom GT: Conversion of waste cooked rice into maltose by a Bacillus subtilis-derived maltogenic amylase and production of maltobionic acid from the prepared maltose using genetically modified Pseudomonas taetrolens. Bioprocess Biosyst Eng. 2023 Feb;46(2):273-277. doi: 10.1007/s00449-022-02832-7. Epub 2022 Dec 16. [PubMed:36526877 ]
Suehiro D, Moriwaki Y, Fukami K, Abe-Dohmae S, Ohnishi M: The effect of maltobionic acid on bone metabolism markers in healthy Japanese postmenopausal women: A randomized double-blind placebo-controlled crossover study. Food Sci Nutr. 2022 Apr 1;10(8):2496-2504. doi: 10.1002/fsn3.2855. eCollection 2022 Aug. [PubMed:35959256 ]
de Souza RC, da Silva LM, Carra S, Flores M, Puton BM, Malvessi E, Valduga E, Zeni J: High-sodium maltobionate production by immobilized Zymomonas mobilis cells in polyurethane. Bioprocess Biosyst Eng. 2022 Sep;45(9):1465-1476. doi: 10.1007/s00449-022-02756-2. Epub 2022 Jul 25. [PubMed:35876965 ]
Oh YR, Jang YA, Song JK, Eom GT: Whole-cell biocatalysis using genetically modified Pseudomonas taetrolens for efficient production of maltobionic acid from pure maltose and high-maltose corn syrup. Bioprocess Biosyst Eng. 2022 May;45(5):901-909. doi: 10.1007/s00449-022-02708-w. Epub 2022 Feb 24. [PubMed:35201399 ]
Oh YR, Jang YA, Hong SH, Eom GT: High-level production of maltobionic acid from high-maltose corn syrup by genetically engineered Pseudomonas taetrolens. Biotechnol Rep (Amst). 2020 Nov 12;28:e00558. doi: 10.1016/j.btre.2020.e00558. eCollection 2020 Dec. [PubMed:33294406 ]
Tanabe K, Okuda A, Ken F, Yamanaka N, Nakamura S, Oku T: Metabolic fate of newly developed nondigestible oligosaccharide, maltobionic acid, in rats and humans. Food Sci Nutr. 2020 May 20;8(7):3610-3616. doi: 10.1002/fsn3.1643. eCollection 2020 Jul. [PubMed:32724623 ]
Suehiro D, Nishio A, Kawai J, Fukami K, Ohnishi M: Effects of corn syrup solids containing maltobionic acid (maltobionic acid calcium salt) on bone resorption in healthy Japanese adult women: A randomized double-blind placebo-controlled crossover study. Food Sci Nutr. 2020 Jan 9;8(2):1030-1037. doi: 10.1002/fsn3.1387. eCollection 2020 Feb. [PubMed:32148811 ]
Wu H, Lu H, Xiao W, Yang J, Du H, Shen Y, Qu H, Jia B, Manna SK, Ramachandran M, Xue X, Ma Z, Xu X, Wang Z, He Y, Lam KS, Zawadzki RJ, Li Y, Lin TY: Sequential Targeting in Crosslinking Nanotheranostics for Tackling the Multibarriers of Brain Tumors. Adv Mater. 2020 Apr;32(14):e1903759. doi: 10.1002/adma.201903759. Epub 2020 Feb 20. [PubMed:32078198 ]
Fukami K, Suehiro D, Ohnishi M: In Vitro Utilization Characteristics of Maltobionic Acid and Its Effects on Bowel Movements in Healthy Subjects. J Appl Glycosci (1999). 2020 Feb 20;67(1):1-9. doi: 10.5458/jag.jag.JAG-2019_0013. eCollection 2020. [PubMed:34429693 ]
Ma X, Kan Z, Du Y, Yang J, Feng Z, Zhu X, Chen C: Enantioseparation of amino alcohol drugs by nonaqueous capillary electrophoresis with a maltobionic acid-based ionic liquid as the chiral selector. Analyst. 2019 Dec 2;144(24):7468-7477. doi: 10.1039/c9an01162e. [PubMed:31710318 ]
Suehiro D, Kawase H, Uehara S, Kawase R, Fukami K, Nakagawa T, Shimada M, Hayakawa T: Maltobionic acid accelerates recovery from iron deficiency-induced anemia in rats. Biosci Biotechnol Biochem. 2020 Feb;84(2):393-401. doi: 10.1080/09168451.2019.1676694. Epub 2019 Oct 12. [PubMed:31608802 ]
Suehiro D, Okada M, Fukami K, Nakagawa T, Hayakawa T: Maltobionic acid enhances intestinal absorption of calcium and magnesium in rats. Biosci Biotechnol Biochem. 2019 Sep;83(9):1766-1773. doi: 10.1080/09168451.2019.1611411. Epub 2019 May 6. [PubMed:31056002 ]
Mao S, Liu Y, Hou Y, Ma X, Yang J, Han H, Wu J, Jia L, Qin H, Lu F: Efficient production of sugar-derived aldonic acids by Pseudomonas fragi TCCC11892. RSC Adv. 2018 Nov 30;8(70):39897-39901. doi: 10.1039/c8ra07556e. eCollection 2018 Nov 28. [PubMed:35558231 ]

Showing NP-Card for Maltobionic acid (NP0336722)

MOL for NP0336722 (Maltobionic acid)

3D MOL for NP0336722 (Maltobionic acid)

3D SDF for NP0336722 (Maltobionic acid)

3D-SDF for NP0336722 (Maltobionic acid)

PDB for NP0336722 (Maltobionic acid)

3D PDB for NP0336722 (Maltobionic acid)

SMILES for NP0336722 (Maltobionic acid)

INCHI for NP0336722 (Maltobionic acid)

Structure for NP0336722 (Maltobionic acid)

3D Structure for NP0336722 (Maltobionic acid)