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Showing NP-Card for Lotaustralin (NP0047771)

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Record Information
Version2.0
Created at2022-03-17 20:45:41 UTC
Updated at2022-03-17 20:45:41 UTC
NP-MRD IDNP0047771
Secondary Accession NumbersNone
Natural Product Identification
Common NameLotaustralin
DescriptionLotaustralin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Lotaustralin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lotaustralin has been detected, but not quantified in, several different foods, such as orange bell peppers, pepper (capsicum), chinese cabbages, kombus, and european cranberries. This could make lotaustralin a potential biomarker for the consumption of these foods. Lotaustralin is structurally related to linamarin, another glucoside found in these plants, and differs from it only by the presence of an extra methyl group. Both lotaustralin and linamarin may be hydrolysed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide. Lotaustralin is found in Acacia aroma , Apis cerana, Berberidopsis beckleri, Dorycnium spp., Euphorbia hirta, Euphorbia supina, Haloragis erecta , Hevea brasiliensis, Hevea pauciflora, Hevea spruceana, Linum austriacum, Linum grandiflorum, Lotus arabicus, Lotus arenarius, Lotus australis, Lotus conjugatus, Lotus corniculatus , Lotus creticus, Lotus edulis , Lotus glaber, Lotus krylovii, Lotus maroccanus, Lotus ornithopodioides, Lotus parviflorus, Lotus tetragonolobus , Ornithopus, Ornithopus perpusillus, Ornithopus pinnatus, Osteospermum ecklonis, Passiflora adenopoda DC., Passiflora lutea L. , Passiflora morifolia Mast., Passiflora pendens, Passiflora pendens MacDougal, Passiflora spp., Rhodiola kirilowii, Rhodiola rosea, Rhodiola sachalinensis , Rhodiola sacra, Rhodiola semenovii, Tetragonolobus spp., Trifolium nigrescens, Trifolium occidentale, Trifolium repens and Triticum monococcum . Lotaustralin is a cyanogenic glucoside found in small amounts in name giving Fabaceae Lotus australis, cassava (Manihot esculenta), lima bean (Phaseolus lunatus), roseroot (Rhodiola rosea) and white clover (Trifolium repens), among other plants.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047771 (Lotaustralin)


  Mrv0541 02241219432D          

 18 18  0  0  0  0            999 V2000
   -0.2801   -3.0043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826   -1.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826   -0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8857    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    0.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -0.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838   -0.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844   -1.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857   -1.3217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    1.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    0.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    1.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4049    3.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844    1.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 16  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
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3D MOL for NP0047771 (Lotaustralin)

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3D SDF for NP0047771 (Lotaustralin)

  Mrv0541 02241219432D          

 18 18  0  0  0  0            999 V2000
   -0.2801   -3.0043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826   -1.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826   -0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8857    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    0.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -0.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838   -0.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844   -1.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857   -1.3217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819    1.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    0.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    1.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4049    3.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844    1.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 16  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3

> <INCHI_KEY>
WEWBWVMTOYUPHH-UHFFFAOYSA-N

> <FORMULA>
C11H19NO6

> <MOLECULAR_WEIGHT>
261.2717

> <EXACT_MASS>
261.121237345

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.890879259950943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.88

> <JCHEM_LOGP>
-1.2294280160000004

> <ALOGPS_LOGS>
-0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199260364821779

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208421962208211

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810842510256697

> <JCHEM_POLAR_SURFACE_AREA>
123.17000000000002

> <JCHEM_REFRACTIVITY>
59.469699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047771 (Lotaustralin)
Download
PDB for NP0047771 (Lotaustralin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -0.523  -5.608   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.514  -3.664   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.514  -0.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.253   0.075   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.075   0.075   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.766   0.075   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.514  -1.121   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.010  -1.121   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.758  -2.467   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.253  -2.467   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.766   2.766   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.514   1.420   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.010   1.420   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.758   0.075   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.253   0.075   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.514   3.664   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.356   5.608   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.758   2.766   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   16                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    6   11   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14    8   13   15                                                  
CONECT   15   14                                                            
CONECT   16    3   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

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3D PDB for NP0047771 (Lotaustralin)
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SMILES for NP0047771 (Lotaustralin)
CCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N
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INCHI for NP0047771 (Lotaustralin)
InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3
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View in JSmol
Synonyms
ValueSource
2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranosideHMDB
2-(beta-D-Glucopyranosyloxy)-2-methyl-(R)-butanenitrileHMDB
2(R)-Hydroxy-2-methylbutyronitrile-beta-D- glucopyranosideMeSH
Lotaustralin, (S)-isomerMeSH
Chemical FormulaC11H19NO6
Average Mass261.2717 Da
Monoisotopic Mass261.12124 Da
IUPAC Name2-methyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
Traditional Name2-methyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
CAS Registry Number534-67-8
SMILES
CCC(C)(OC1OC(CO)C(O)C(O)C1O)C#N
InChI Identifier
InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3
InChI KeyWEWBWVMTOYUPHH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia aromaPlant
Apis ceranaLOTUS Database
Berberidopsis beckleriLOTUS Database
Dorycnium spp.Plant
Euphorbia hirtaLOTUS Database
Euphorbia supinaLOTUS Database
Haloragis erectaPlant
Hevea brasiliensisLOTUS Database
Hevea paucifloraLOTUS Database
Hevea spruceanaLOTUS Database
Linum austriacumLOTUS Database
Linum grandiflorumLOTUS Database
Linum usitatissimumFooDB
Lotus arabicusPlant
Lotus arenariusPlant
Lotus australisPlant
Lotus conjugatusPlant
Lotus corniculatusPlant
Lotus creticusLOTUS Database
Lotus edulisPlant
Lotus glaberPlant
Lotus kryloviiPlant
Lotus maroccanusPlant
Lotus ornithopodioidesPlant
Lotus parviflorusPlant
Lotus tetragonolobusPlant
Manihot esculentaFooDB
Ornithopus-
Ornithopus perpusillusPlant
Ornithopus pinnatusPlant
Osteospermum ecklonisLOTUS Database
Passiflora adenopoda DC.Plant
Passiflora lutea L.Plant
Passiflora morifolia Mast.Plant
Passiflora pendensLOTUS Database
Passiflora pendens MacDougalPlant
Passiflora spp.Plant
Rhodiola kirilowiiPlant
Rhodiola roseaLOTUS Database
Rhodiola sachalinensisPlant
Rhodiola sacraLOTUS Database
Rhodiola semenoviiLOTUS Database
Tetragonolobus spp.-
Trifolium nigrescensPlant
Trifolium occidentaleLOTUS Database
Trifolium repensPlant
Triticum monococcumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentCyanogenic glycosides  
Alternative Parents
Substituents
  • Cyanogenic glycoside
    • 

  • Hexose monosaccharide
    • 

  • O-glycosyl compound
    • 

  • Monosaccharide
    • 

  • Oxane
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Acetal
    • 

  • Primary alcohol
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.88ALOGPS
logP-1.2ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.17 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.47 m³·mol⁻¹ChemAxon
Polarizability25.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033865  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012049  
KNApSAcK IDNot Available
Chemspider ID3817241  
KEGG Compound IDC08334  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLotaustralin  
METLIN IDNot Available
PubChem Compound4626626  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available