NP-MRD: Showing NP-Card for Levan (NP0087064)

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Record Information

Version

2.0

Created at

2022-05-11 16:38:57 UTC

Updated at

2022-05-11 16:38:57 UTC

NP-MRD ID

NP0087064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Levan

Description

Levan, also known as fructan or levan N, 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. Levan was first documented in 2003 (PMID: 14627303). Levan is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Untitled Document-6
  Mrv0541 02231219452D          

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M  END

     RDKit          3D

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M  END

Untitled Document-6
  Mrv0541 02231219452D          

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M  END
> <DATABASE_ID>
NP0087064

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O16/c19-1-7-9(23)14(28)18(5-22,33-7)31-2-8-10(24)12(26)16(3-20,32-8)6-30-15-11(25)13(27)17(29,4-21)34-15/h7-15,19-29H,1-6H2/t7-,8-,9-,10-,11+,12+,13+,14+,15+,16+,17-,18-/m1/s1

> <INCHI_KEY>
AIHDCSAXVMAMJH-GFBKWZILSA-N

> <FORMULA>
C18H32O16

> <MOLECULAR_WEIGHT>
504.4371

> <EXACT_MASS>
504.169034976

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
47.61786684364046

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5S)-5-{[(2S,3S,4S,5R)-5-({[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]methoxy}-2-(hydroxymethyl)oxolane-2,3,4-triol

> <ALOGPS_LOGP>
-2.89

> <JCHEM_LOGP>
-6.261129065666667

> <ALOGPS_LOGS>
-0.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.813760387003148

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.22617457834656

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4539656704035

> <JCHEM_POLAR_SURFACE_AREA>
268.67999999999995

> <JCHEM_REFRACTIVITY>
101.8442

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fructans

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-6                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.830   5.257   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.830   3.717   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.295   3.241   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.200   4.487   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.295   5.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.475   1.906   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.314   0.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.808   0.054   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.038   1.388   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.068   2.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.488  -3.396   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.488  -4.936   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.024  -5.412   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.881  -4.166   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.024  -2.920   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.838   3.866   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.459  -0.656   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.310  -2.150   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.734  -5.841   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.344   5.517   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.416   6.162   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.823   3.438   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.416   2.811   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.771   7.197   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.344   3.456   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.650  -1.513   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.182  -1.353   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.734  -2.491   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.452  -6.877   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.809   2.676   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.809   5.041   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.378   3.866   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.644  -2.920   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.959  -7.197   0.000  0.00  0.00           O+0
CONECT    1    2    5   21                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20   25                                             
CONECT    5    4    1   24                                                  
CONECT    6    7   10   30                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   16   22                                             
CONECT   11   12   15   28                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   11   18   26                                             
CONECT   16   10   32                                                       
CONECT   17    7                                                            
CONECT   18   15   33                                                       
CONECT   19   12                                                            
CONECT   20    4   31                                                       
CONECT   21    1                                                            
CONECT   22   10   23                                                       
CONECT   23    2   22                                                       
CONECT   24    5                                                            
CONECT   25    4                                                            
CONECT   26   15   27                                                       
CONECT   27    8   26                                                       
CONECT   28   11                                                            
CONECT   29   13   34                                                       
CONECT   30    6                                                            
CONECT   31   20                                                            
CONECT   32   16                                                            
CONECT   33   18                                                            
CONECT   34   29                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2,6-beta-D-Fructosyl)N	HMDB
(2,6-beta-D-Fructosyl)n+1	HMDB
(2,6-beta-delta-Fructosyl)N	HMDB
(2,6-beta-delta-Fructosyl)n+1	HMDB
2,6-beta-D-Fructan	HMDB
2,6-beta-delta-Fructan	HMDB
Fructan	HMDB
Levan N	HMDB

Chemical Formula

C₁₈H₃₂O₁₆

Average Mass

504.4371 Da

Monoisotopic Mass

504.16903 Da

IUPAC Name

(2R,3S,4S,5S)-5-{[(2S,3S,4S,5R)-5-({[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]methoxy}-2-(hydroxymethyl)oxolane-2,3,4-triol

Traditional Name

fructans

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H32O16/c19-1-7-9(23)14(28)18(5-22,33-7)31-2-8-10(24)12(26)16(3-20,32-8)6-30-15-11(25)13(27)17(29,4-21)34-15/h7-15,19-29H,1-6H2/t7-,8-,9-,10-,11+,12+,13+,14+,15+,16+,17-,18-/m1/s1

InChI Key

AIHDCSAXVMAMJH-GFBKWZILSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

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

C-glycosyl compound
Disaccharide
O-glycosyl compound
Ketal
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Dialkyl ether
Acetal
Primary alcohol
Hydrocarbon derivative
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	-2.9	ALOGPS
logP	-6.3	ChemAxon
logS	-0.21	ALOGPS
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	-3.5	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	10	ChemAxon
Refractivity	101.84 m³·mol⁻¹	ChemAxon
Polarizability	47.62 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

HMDB0003539

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023192

KNApSAcK ID

Not Available

Chemspider ID

17216231

KEGG Compound ID

C01355

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levan

METLIN ID

6945

PubChem Compound

22833608

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kleessen B, Elsayed NA, Loehren U, Schroedl W, Krueger M: Jerusalem artichokes stimulate growth of broiler chickens and protect them against endotoxins and potential cecal pathogens. J Food Prot. 2003 Nov;66(11):2171-5. doi: 10.4315/0362-028x-66.11.2171. [PubMed:14627303 ]

Showing NP-Card for Levan (NP0087064)

MOL for NP0087064 (Levan)

3D MOL for NP0087064 (Levan)

3D SDF for NP0087064 (Levan)

3D-SDF for NP0087064 (Levan)

PDB for NP0087064 (Levan)

3D PDB for NP0087064 (Levan)

SMILES for NP0087064 (Levan)

INCHI for NP0087064 (Levan)

Structure for NP0087064 (Levan)

3D Structure for NP0087064 (Levan)