NP-MRD: Showing NP-Card for Trehalulose (NP0338224)

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Record Information

Version

2.0

Created at

2024-09-11 14:26:56 UTC

Updated at

2024-09-11 14:26:56 UTC

NP-MRD ID

NP0338224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trehalulose

Description

Trehalulose belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Trehalulose was first documented in 2024 (PMID: 38890884). Based on a literature review a small amount of articles have been published on Trehalulose (PMID: 38688341) (PMID: 38260771) (PMID: 38124990) (PMID: 37862235).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262316592D          

 23 24  0  0  0  0            999 V2000
    4.8764    7.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    6.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5793    5.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3863    5.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9383    6.2021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273    5.1475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2822    4.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302    3.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    3.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712    3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191    3.9213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4482    4.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    4.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0892    4.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3441    3.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0891    1.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686    1.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7837    2.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0386    2.8233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    3.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    2.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587    2.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737    1.3712    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  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  1  0  0  0  0
 10 21  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O)(COC2OC(CO)C(O)C(O)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-3-12(20)10(19)7(16)5(2-14)23-12/h4-11,13-20H,1-3H2

> <INCHI_KEY>
NMXLJRHBJVMYPD-UHFFFAOYNA-N

> <FORMULA>
C12H22O11

> <MOLECULAR_WEIGHT>
342.297

> <EXACT_MASS>
342.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.551872740733703

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-6-{[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

> <JCHEM_LOGP>
-4.528834963666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.102334622924015

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.263739088523755

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834350301185

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
68.77409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-6-{[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

> <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       9.103  13.362   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.072  12.218   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.548  10.753   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.054  10.433   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.085  11.577   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.518   9.609   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.993   8.144   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.963   7.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.457   7.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.426   6.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.396   7.320   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      12.037   8.648   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.530   8.968   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.500   7.824   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.976   6.359   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.633   2.721   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.101   2.560   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.196   3.806   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.672   5.270   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.716   5.746   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.180   5.270   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.656   3.806   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.751   2.560   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19   21                                             
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    4   12   14                                                  
CONECT   14    7   13   15                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   10   18                                                       
CONECT   20   21                                                            
CONECT   21   10   20   22                                                  
CONECT   22   18   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₂₂O₁₁

Average Mass

342.2970 Da

Monoisotopic Mass

342.11621 Da

IUPAC Name

2-(hydroxymethyl)-6-{[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

Traditional Name

2-(hydroxymethyl)-6-{[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OCC1OC(O)(COC2OC(CO)C(O)C(O)C2O)C(O)C1O

InChI Identifier

InChI=1/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-3-12(20)10(19)7(16)5(2-14)23-12/h4-11,13-20H,1-3H2

InChI Key

NMXLJRHBJVMYPD-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
C-glycosyl compound
Oxane
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-4.5	ChemAxon
pKa (Strongest Acidic)	10.26	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.77 m³·mol⁻¹	ChemAxon
Polarizability	31.55 Å³	ChemAxon
Number of Rings	2	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

Trehalulose

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mello Dos Santos M, Khan N, Lim LY, Locher C: Antioxidant Activity, Physicochemical and Sensory Properties of Stingless Bee Honey from Australia. Foods. 2024 May 25;13(11):1657. doi: 10.3390/foods13111657. [PubMed:38890884 ]
Lee CY, So YS, Lim MC, Jeong S, Yoo SH, Park CS, Jung JH, Seo DH: Characterization of a unique pH-dependent amylosucrase from Deinococcus cellulosilyticus. Int J Biol Macromol. 2024 Jun;269(Pt 2):131834. doi: 10.1016/j.ijbiomac.2024.131834. Epub 2024 Apr 29. [PubMed:38688341 ]
Turck D, Bohn T, Castenmiller J, De Henauw S, Hirsch-Ernst KI, Maciuk A, Mangelsdorf I, McArdle HJ, Naska A, Pentieva K, Siani A, Thies F, Tsabouri S, Vinceti M, Aguilera-Gomez M, Cubadda F, Frenzel T, Heinonen M, Marchelli R, Neuhauser-Berthold M, Poulsen M, Prieto Maradona M, Schlatter JR, Siskos A, van Loveren H, Ferreira da Costa L, Albert O, Knutsen HK: Safety of isomaltulose syrup (dried) as a novel food pursuant to Regulation (EU) 2015/2283. EFSA J. 2024 Jan 22;22(1):e8491. doi: 10.2903/j.efsa.2024.8491. eCollection 2024 Jan. [PubMed:38260771 ]
Rosli MA, Mohd Nasir NA, Mustafa MZ, Othman MA, Zakaria Z, Halim AS: Effectiveness of stingless bee (Kelulut) honey versus conventional gel dressing in diabetic wound bed preparation: A randomized controlled trial. J Taibah Univ Med Sci. 2023 Nov 24;19(1):209-219. doi: 10.1016/j.jtumed.2023.11.003. eCollection 2024 Feb. [PubMed:38124990 ]
Ramlan NAFM, Mohamad Azman E, Muhammad K, Jusoh AZ, Johari NA, Yusof YA, Zawawi N: Physicochemical homogeneity of stingless bee honey (Heterotrigona itama) produced in the west coast, east coast and inland area of Peninsular Malaysia. J Sci Food Agric. 2024 Feb;104(3):1756-1767. doi: 10.1002/jsfa.13067. Epub 2023 Nov 15. [PubMed:37862235 ]

Showing NP-Card for Trehalulose (NP0338224)

MOL for NP0338224 (Trehalulose)

3D MOL for NP0338224 (Trehalulose)

3D SDF for NP0338224 (Trehalulose)

3D-SDF for NP0338224 (Trehalulose)

PDB for NP0338224 (Trehalulose)

3D PDB for NP0338224 (Trehalulose)

SMILES for NP0338224 (Trehalulose)

INCHI for NP0338224 (Trehalulose)

Structure for NP0338224 (Trehalulose)

3D Structure for NP0338224 (Trehalulose)