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Showing NP-Card for n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid (NP0223511)

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Record Information
Version2.0
Created at2022-09-06 01:37:38 UTC
Updated at2022-09-06 01:37:38 UTC
NP-MRD IDNP0223511
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid
DescriptionTolbutamide, also known as orinase or diaval, belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. Tolbutamide is a drug which is used for treatment of niddm (non-insulin-dependent diabetes mellitus) in conjunction with diet and exercise. Tolbutamide is a weakly acidic compound (based on its pKa). n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid is found in Homo sapiens. n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid was first documented in 2001 (PMID: 11840346). An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position (PMID: 11835228) (PMID: 11911494) (PMID: 12042355).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)

1124
  Mrv0541 02231215162D          

 18 18  0  0  0  0            999 V2000
    2.4751   -0.6188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  4 12  2  0  0  0  0
  5  8  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
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3D MOL for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)

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3D SDF for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)
1124
  Mrv0541 02231215162D          

 18 18  0  0  0  0            999 V2000
    2.4751   -0.6188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  4 12  2  0  0  0  0
  5  8  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

> <INCHI_KEY>
JLRGJRBPOGGCBT-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O3S

> <MOLECULAR_WEIGHT>
270.348

> <EXACT_MASS>
270.103813142

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.09953664240288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-butyl-1-(4-methylbenzenesulfonyl)urea

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.295335827333333

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.114800808981375

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.333945172256472

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
70.27

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tolbutamide

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)
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PDB for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1124                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620  -1.155   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.080  -1.155   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160  -1.155   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.288   0.385   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.954   2.695   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.620   0.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.288   5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.288   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.621   5.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.621   7.315   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954   1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286  -3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.620  -5.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.286  -5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.954  -5.005   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.620  -7.315   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   10                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   12                                                            
CONECT    5    8   12                                                       
CONECT    6    1   12                                                       
CONECT    7    8    9                                                       
CONECT    8    5    7                                                       
CONECT    9    7   11                                                       
CONECT   10    1   13   14                                                  
CONECT   11    9                                                            
CONECT   12    4    5    6                                                  
CONECT   13   10   16                                                       
CONECT   14   10   17                                                       
CONECT   15   16   17   18                                                  
CONECT   16   13   15                                                       
CONECT   17   14   15                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

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3D PDB for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)
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SMILES for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)
CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1
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INCHI for NP0223511 (n-(4-methylbenzenesulfonyl)butane-1-carbamimidic acid)
InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)
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View in JSmol
Synonyms
ValueSource
1-Butyl-3-(p-methylphenylsulfonyl)ureaChEBI
1-Butyl-3-(p-tolylsulfonyl)ureaChEBI
1-Butyl-3-tosylureaChEBI
1-p-Toluenesulfonyl-3-butylureaChEBI
3-(p-Tolyl-4-sulfonyl)-1-butylureaChEBI
N-(4-Methylbenzenesulfonyl)-n'-butylureaChEBI
N-(4-Methylphenylsulfonyl)-n'-butylureaChEBI
N-(p-Methylbenzenesulfonyl)-n'-butylureaChEBI
N-(Sulfonyl-p-methylbenzene)-n'-N-butylureaChEBI
N-Butyl-n'-(4-methylphenylsulfonyl)ureaChEBI
N-Butyl-n'-(p-tolylsulfonyl)ureaChEBI
N-Butyl-n'-p-toluenesulfonylureaChEBI
N-N-Butyl-n'-tosylureaChEBI
OrinaseChEBI
TolbutamidaChEBI
TolbutamidumChEBI
TolylsulfonylbutylureaChEBI
1-Butyl-3-(p-methylphenylsulphonyl)ureaGenerator
1-Butyl-3-(p-tolylsulphonyl)ureaGenerator
1-p-Toluenesulphonyl-3-butylureaGenerator
3-(p-Tolyl-4-sulphonyl)-1-butylureaGenerator
N-(4-Methylbenzenesulphonyl)-n'-butylureaGenerator
N-(4-Methylphenylsulphonyl)-n'-butylureaGenerator
N-(p-Methylbenzenesulphonyl)-n'-butylureaGenerator
N-(Sulphonyl-p-methylbenzene)-n'-N-butylureaGenerator
N-Butyl-n'-(4-methylphenylsulphonyl)ureaGenerator
N-Butyl-n'-(p-tolylsulphonyl)ureaGenerator
N-Butyl-n'-p-toluenesulphonylureaGenerator
TolylsulphonylbutylureaGenerator
Berlin chemie brand OF tolbutamideHMDB
Berlin-chemie brand OF tolbutamideHMDB
DiavalHMDB
RastinonHMDB
Tolbutamid r.a.n.HMDB
Yamanouchi brand OF tolbutamideHMDB
ArtosinHMDB
Hoechst brand OF tolbutamideHMDB
OrabetHMDB
Tolbutamide butamide brandHMDB
Tolbutamide hoechst brandHMDB
Apo-tolbutamideHMDB
Butamide brand OF tolbutamideHMDB
DolipolHMDB
Pfizer brand OF tolbutamideHMDB
Tolbutamide aventis brandHMDB
Valdecasas brand OF tolbutamideHMDB
Apotex brand OF tolbutamideHMDB
Aventis brand OF tolbutamideHMDB
DiabetolHMDB
R.A.N. brand OF tolbutamideHMDB
Tolbutamide pfizer brandHMDB
Chemical FormulaC12H18N2O3S
Average Mass270.3480 Da
Monoisotopic Mass270.10381 Da
IUPAC Name3-butyl-1-(4-methylbenzenesulfonyl)urea
Traditional Nametolbutamide
CAS Registry NumberNot Available
SMILES
CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)
InChI KeyJLRGJRBPOGGCBT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Homo sapiensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzenesulfonamides  
Direct ParentBenzenesulfonamides  
Alternative Parents
Substituents
  • Benzenesulfonamide
    • 

  • Tosyl compound
    • 

  • Benzenesulfonyl group
    • 

  • Toluene
    • 

  • Sulfonylurea
    • 

  • Organic sulfonic acid or derivatives
    • 

  • Organosulfonic acid or derivatives
    • 

  • Sulfonyl
    • 

  • Aminosulfonyl compound
    • 

  • Carboximidic acid derivative
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP2.04ALOGPS
logP2.3ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.27 m³·mol⁻¹ChemAxon
Polarizability29.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0015256  
DrugBank IDDB01124  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5304  
KEGG Compound IDC07148  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolbutamide  
METLIN IDNot Available
PubChem Compound5505  
PDB IDNot Available
ChEBI ID27999  
Good Scents IDNot Available
References
General References
  1. Smoak IW: Tolbutamide alters glucose transport and metabolism in the embryonic mouse heart. Teratology. 2002 Jan;65(1):19-25. doi: 10.1002/tera.1094. [PubMed:11835228  ] 
  2. Kodama T, Oku H, Kawamura H, Sakagami K, Puro DG: Platelet-derived growth factor-BB: a survival factor for the retinal microvasculature during periods of metabolic compromise. Curr Eye Res. 2001 Aug;23(2):93-7. doi: 10.1076/ceyr.23.2.93.5476. [PubMed:11840346  ] 
  3. Liu SH, Lin-Shiau SY: Mercuric chloride alters the membrane potential and intracellular calcium level in mouse pancreatic islet cells. J Toxicol Environ Health A. 2002 Feb;65(3-4):317-26. doi:  10.1080/15287390252800891. [PubMed:11911494  ] 
  4. Matsumoto N, Komiyama S, Akaike N: Pre- and postsynaptic ATP-sensitive potassium channels during metabolic inhibition of rat hippocampal CA1 neurons. J Physiol. 2002 Jun 1;541(Pt 2):511-20. doi: 10.1113/jphysiol.2002.018267. [PubMed:12042355  ] 
  5. LOTUS database [Link]