NP-MRD: Showing NP-Card for laminarin (NP0291516)

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Record Information

Version

1.0

Created at

2022-09-09 22:38:25 UTC

Updated at

2022-09-09 22:38:25 UTC

NP-MRD ID

NP0291516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

laminarin

Description

Laminaran 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. laminarin is found in Ascoseira mirabilis, Chorda filum, Cystoseira barbata, Padina antillarum, Padina tetrastromatica and Pleurotus ostreatus. It was first documented in 2021 (PMID: 34677439). Based on a literature review a significant number of articles have been published on Laminaran (PMID: 35873409) (PMID: 34825909) (PMID: 34578399) (PMID: 34453982).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102200382D          

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M  END
> <DATABASE_ID>
NP0291516

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O16/c19-1-4-7(22)10(25)11(26)17(31-4)34-15-9(24)6(3-21)32-18(13(15)28)33-14-8(23)5(2-20)30-16(29)12(14)27/h4-29H,1-3H2/t4-,5-,6-,7-,8-,9-,10+,11-,12-,13-,14+,15+,16?,17?,18?/m1/s1

> <INCHI_KEY>
DBTMGCOVALSLOR-VPNXCSTESA-N

> <FORMULA>
C18H32O16

> <MOLECULAR_WEIGHT>
504.438

> <EXACT_MASS>
504.16903495

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.97336272644683

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4S,5S,6R)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-6.474210509333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.956407677931654

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.21486717533891

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483775752750818

> <JCHEM_POLAR_SURFACE_AREA>
268.67999999999995

> <JCHEM_REFRACTIVITY>
100.75000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
laminarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   12   22                                                  
CONECT   22   21                                                            
CONECT   23   10   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24    7   28                                                  
CONECT   28   27                                                            
CONECT   29    5   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
Laminarin	MeSH

Chemical Formula

C₁₈H₃₂O₁₆

Average Mass

504.4380 Da

Monoisotopic Mass

504.16903 Da

IUPAC Name

(3R,4S,5S,6R)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

laminarin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H32O16/c19-1-4-7(22)10(25)11(26)17(31-4)34-15-9(24)6(3-21)32-18(13(15)28)33-14-8(23)5(2-20)30-16(29)12(14)27/h4-29H,1-3H2/t4-,5-,6-,7-,8-,9-,10+,11-,12-,13-,14+,15+,16?,17?,18?/m1/s1

InChI Key

DBTMGCOVALSLOR-VPNXCSTESA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ascoseira mirabilis	LOTUS Database	35616633
Chorda filum	LOTUS Database	35616633
Cystoseira barbata	LOTUS Database	35616633
Padina antillarum	LOTUS Database	35616633
Padina tetrastromatica	LOTUS Database	35616633
Pleurotus ostreatus	LOTUS Database	35616633

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
O-glycosyl compound
Glycosyl compound
Oxane
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	-6.5	ChemAxon
pKa (Strongest Acidic)	11.21	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	7	ChemAxon
Refractivity	100.75 m³·mol⁻¹	ChemAxon
Polarizability	45.97 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

388438

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Laminarin

METLIN ID

Not Available

PubChem Compound

439306

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cheong KL, Li JK, Zhong S: Preparation and Structure Characterization of High-Value Laminaria digitata Oligosaccharides. Front Nutr. 2022 Jul 7;9:945804. doi: 10.3389/fnut.2022.945804. eCollection 2022. [PubMed:35873409 ]
Zargarzadeh M, Silva AS, Nunes C, Coimbra MA, Custodio CA, Mano JF: Self-glucose feeding hydrogels by enzyme empowered degradation for 3D cell culture. Mater Horiz. 2022 Feb 7;9(2):694-707. doi: 10.1039/d0mh01982h. [PubMed:34825909 ]
Malyarenko OS, Malyarenko TV, Usoltseva RV, Surits VV, Kicha AA, Ivanchina NV, Ermakova SP: Combined Anticancer Effect of Sulfated Laminaran from the Brown Alga Alaria angusta and Polyhydroxysteroid Glycosides from the Starfish Protoreaster lincki on 3D Colorectal Carcinoma HCT 116 Cell Line. Mar Drugs. 2021 Sep 25;19(10):540. doi: 10.3390/md19100540. [PubMed:34677439 ]
Geetha Bai R, Tuvikene R: Potential Antiviral Properties of Industrially Important Marine Algal Polysaccharides and Their Significance in Fighting a Future Viral Pandemic. Viruses. 2021 Sep 13;13(9):1817. doi: 10.3390/v13091817. [PubMed:34578399 ]
Jeong DW, Hyeon JE, Lee ME, Ko YJ, Kim M, Han SO: Efficient utilization of brown algae for the production of Polyhydroxybutyrate (PHB) by using an enzyme complex immobilized on Ralstonia eutropha. Int J Biol Macromol. 2021 Oct 31;189:819-825. doi: 10.1016/j.ijbiomac.2021.08.149. Epub 2021 Aug 26. [PubMed:34453982 ]
LOTUS database [Link]

Showing NP-Card for laminarin (NP0291516)

MOL for NP0291516 (laminarin)

3D MOL for NP0291516 (laminarin)

3D SDF for NP0291516 (laminarin)

3D-SDF for NP0291516 (laminarin)

PDB for NP0291516 (laminarin)

3D PDB for NP0291516 (laminarin)

SMILES for NP0291516 (laminarin)

INCHI for NP0291516 (laminarin)

Structure for NP0291516 (laminarin)

3D Structure for NP0291516 (laminarin)