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Showing NP-Card for Linustatin (NP0049140)

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Record Information
Version2.0
Created at2022-03-17 21:07:45 UTC
Updated at2022-03-17 21:07:45 UTC
NP-MRD IDNP0049140
Secondary Accession NumbersNone
Natural Product Identification
Common NameLinustatin
Description Linustatin is found in Hevea brasiliensis, Hevea pauciflora, Manihot esculenta, Passiflora pendens and Passiflora spp..
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049140 (Linustatin)


  Mrv0541 02241215442D          

 28 29  0  0  0  0            999 V2000
    3.3250   -1.5221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -2.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622   -1.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834    1.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834    2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    3.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -1.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403   -2.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250   -2.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -0.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1206    0.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410    2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    3.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1231   -2.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1206    2.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423   -3.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423   -2.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2 27  1  0  0  0  0
  3  4  1  0  0  0  0
  3 27  1  0  0  0  0
  4  5  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 23  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
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3D MOL for NP0049140 (Linustatin)

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3D SDF for NP0049140 (Linustatin)

  Mrv0541 02241215442D          

 28 29  0  0  0  0            999 V2000
    3.3250   -1.5221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -2.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622   -1.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    0.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834    1.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834    2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    3.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -1.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403   -2.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250   -2.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -0.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -0.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1206    0.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410    2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    3.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1231   -2.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1206    2.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423   -3.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423   -2.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2 27  1  0  0  0  0
  3  4  1  0  0  0  0
  3 27  1  0  0  0  0
  4  5  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 23  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C16H27NO11/c1-16(2,5-17)28-15-13(11(23)9(21)7(4-19)26-15)27-14-12(24)10(22)8(20)6(3-18)25-14/h6-15,18-24H,3-4H2,1-2H3

> <INCHI_KEY>
STZOICDLLWZNHE-UHFFFAOYSA-N

> <FORMULA>
C16H27NO11

> <MOLECULAR_WEIGHT>
409.3857

> <EXACT_MASS>
409.158410711

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
39.139920527560264

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.90

> <JCHEM_LOGP>
-3.5227860566666678

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.700587489289653

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.089839570060487

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835766873804

> <JCHEM_POLAR_SURFACE_AREA>
202.31999999999996

> <JCHEM_REFRACTIVITY>
87.35900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049140 (Linustatin)
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PDB for NP0049140 (Linustatin)
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       6.207  -2.841   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.010  -4.337   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.916  -2.393   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.916   1.794   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.262   2.542   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.262   4.038   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.609   4.786   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.609   6.282   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.674  -2.841   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.822  -2.841   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.570  -4.187   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.822  -5.534   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -6.207  -4.187   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.459  -2.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.813  -2.841   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.066  -1.495   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.570  -1.495   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.225   1.794   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.570   2.542   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.570   4.038   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.916   4.786   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.916   6.282   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.066  -4.187   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.963  -5.534   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.225   4.786   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.066  -6.282   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.066  -4.337   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.121  -4.786   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1   27                                                       
CONECT    3    4   27                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   17                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    4   18   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21    6   20   22                                                  
CONECT   22   21                                                            
CONECT   23   11   15   24                                                  
CONECT   24   23                                                            
CONECT   25   20                                                            
CONECT   26   27                                                            
CONECT   27    2    3   26   28                                             
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

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3D PDB for NP0049140 (Linustatin)
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SMILES for NP0049140 (Linustatin)
CC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C#N
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INCHI for NP0049140 (Linustatin)
InChI=1S/C16H27NO11/c1-16(2,5-17)28-15-13(11(23)9(21)7(4-19)26-15)27-14-12(24)10(22)8(20)6(3-18)25-14/h6-15,18-24H,3-4H2,1-2H3
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SynonymsNot Available
Chemical FormulaC16H27NO11
Average Mass409.3857 Da
Monoisotopic Mass409.15841 Da
IUPAC Name2-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-methylpropanenitrile
Traditional Name2-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-methylpropanenitrile
CAS Registry Number72229-40-4
SMILES
CC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C#N
InChI Identifier
InChI=1S/C16H27NO11/c1-16(2,5-17)28-15-13(11(23)9(21)7(4-19)26-15)27-14-12(24)10(22)8(20)6(3-18)25-14/h6-15,18-24H,3-4H2,1-2H3
InChI KeySTZOICDLLWZNHE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Hevea brasiliensisLOTUS Database
Hevea paucifloraLOTUS Database
Linum usitatissimumFooDB
Manihot esculentaLOTUS Database
Passiflora pendensLOTUS Database
Passiflora spp.Plant
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
    • 

  • Disaccharide
    • 

  • O-glycosyl compound
    • 

  • Oxane
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Acetal
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Oxacycle
    • 

  • Primary alcohol
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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-1.9ALOGPS
logP-3.5ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)12.09ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area202.32 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.36 m³·mol⁻¹ChemAxon
Polarizability39.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017850  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45934451  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available