NP-MRD: Showing NP-Card for 1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol (NP0277933)

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Record Information

Version

2.0

Created at

2022-09-09 02:46:47 UTC

Updated at

2022-09-09 02:46:47 UTC

NP-MRD ID

NP0277933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol

Description

2-(1,2,3,4-Tetrahydroxybutyl)-6-(2,3,4-trihydroxybutyl)pyrazine, also known as 1-[6-(2,3,4-trihydroxybutyl)pyrazinyl]-1,2,3,4-butanetetrol, 9CI, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. 2-(1,2,3,4-Tetrahydroxybutyl)-6-(2,3,4-trihydroxybutyl)pyrazine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(1,2,3,4-Tetrahydroxybutyl)-6-(2,3,4-trihydroxybutyl)pyrazine has been detected, but not quantified in, nuts. 1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol is found in Gynura divaricata. This could make 2-(1,2,3,4-tetrahydroxybutyl)-6-(2,3,4-trihydroxybutyl)pyrazine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    5.0870    0.8153    1.4056 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347   -0.4306    0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.9363    0.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1205   -2.1603   -0.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3611    0.1057   -0.6602 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3173    0.2880   -1.6722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0729   -0.2627   -1.3257 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2547   -1.4403   -2.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9185   -0.3185   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269   -1.4503    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243   -1.5553    1.1926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2150   -0.5536    1.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485    0.5718    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0400    1.6759    0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699    1.5319   -0.2774 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9906    2.6550   -0.3174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777    0.2912   -0.1561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8162    0.2255   -1.2937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8806    0.2687    1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5948   -0.9288    1.0016 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    0.6563   -0.2817 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7047    1.4958    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853   -0.3059   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6992   -1.1760    1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -0.9918    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0388   -2.5158   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    1.0579   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0425   -0.1237   -2.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742    0.5333   -2.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -1.4863   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4046   -2.2918    0.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728   -0.6286    1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3567    1.7322    1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5070    2.6165    0.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6919    1.4853   -1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9280    2.3434   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -0.6384   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1741   -0.6950   -1.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973    0.2451    1.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6178    1.0978    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5440   -0.8028    1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 21  2  0
 21  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  9  7  1  0
  7  8  1  0
  7  5  1  0
  5  6  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  1  0
 12 13  1  0
 20 41  1  0
 19 39  1  0
 19 40  1  0
 17 37  1  1
 18 38  1  0
 15 35  1  6
 16 36  1  0
 14 33  1  0
 14 34  1  0
 10 31  1  0
 12 32  1  0
  7 29  1  6
  8 30  1  0
  5 27  1  1
  6 28  1  0
  3 25  1  1
  4 26  1  0
  2 23  1  0
  2 24  1  0
  1 22  1  0
M  END


  Mrv0541 02241209032D          

 21 21  0  0  0  0            999 V2000
   -3.5712    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    1.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859    0.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7155   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5711   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    1.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859    0.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419   -0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008   -1.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.4095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    1.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3 19  1  0  0  0  0
  7 14  2  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 10 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0277933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)C(O)CC1=NC(=CN=C1)C(O)C(O)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C12H20N2O7/c15-4-9(18)8(17)1-6-2-13-3-7(14-6)11(20)12(21)10(19)5-16/h2-3,8-12,15-21H,1,4-5H2

> <INCHI_KEY>
MBHUNOHYVYVNIP-UHFFFAOYSA-N

> <FORMULA>
C12H20N2O7

> <MOLECULAR_WEIGHT>
304.2964

> <EXACT_MASS>
304.127051004

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
29.511605724554066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol

> <ALOGPS_LOGP>
-2.02

> <JCHEM_LOGP>
-4.596327548

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.090272546114242

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.28345990869065

> <JCHEM_PKA_STRONGEST_BASIC>
0.3822068186018085

> <JCHEM_POLAR_SURFACE_AREA>
167.39000000000001

> <JCHEM_REFRACTIVITY>
68.91859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      -6.666   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.332   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.332   2.309   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -8.000   0.770   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -4.001  -1.539   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.336  -1.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.666  -0.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.332   0.767   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.998  -0.003   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.332   2.306   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.000   0.767   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.998  -1.542   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -0.001  -2.309   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.330  -1.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.330  -0.003   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.001   0.764   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.333   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.664   0.767   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.664   2.306   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2    6   19                                                  
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    3                                                            
CONECT    7   14   18                                                       
CONECT    8    9   12                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   13   20                                                  
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13   10                                                            
CONECT   14    7   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18    7   17   19                                                  
CONECT   19    3   18                                                       
CONECT   20   10   16   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-[6-(2,3,4-Trihydroxybutyl)pyrazinyl]-1,2,3,4-butanetetrol, 9ci	HMDB

Chemical Formula

C₁₂H₂₀N₂O₇

Average Mass

304.2964 Da

Monoisotopic Mass

304.12705 Da

IUPAC Name

1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol

Traditional Name

1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol

CAS Registry Number

Not Available

SMILES

OCC(O)C(O)CC1=NC(=CN=C1)C(O)C(O)C(O)CO

InChI Identifier

InChI=1S/C12H20N2O7/c15-4-9(18)8(17)1-6-2-13-3-7(14-6)11(20)12(21)10(19)5-16/h2-3,8-12,15-21H,1,4-5H2

InChI Key

MBHUNOHYVYVNIP-UHFFFAOYSA-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
Gynura divaricata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Sugar alcohol
Heteroaromatic compound
Secondary alcohol
Polyol
Azacycle
Aromatic alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	ALOGPS
logP	-4.6	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.28	ChemAxon
pKa (Strongest Basic)	0.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	167.39 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	68.92 m³·mol⁻¹	ChemAxon
Polarizability	29.51 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034894

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013470

KNApSAcK ID

Not Available

Chemspider ID

13468534

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12285901

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol (NP0277933)

MOL for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

3D MOL for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

3D SDF for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

3D-SDF for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

PDB for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

3D PDB for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

SMILES for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

INCHI for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

Structure for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)

3D Structure for NP0277933 (1-[6-(2,3,4-trihydroxybutyl)pyrazin-2-yl]butane-1,2,3,4-tetrol)