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Showing NP-Card for acefylline (NP0231624)

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Record Information
Version1.0
Created at2022-09-06 12:34:15 UTC
Updated at2022-09-06 12:34:15 UTC
NP-MRD IDNP0231624
Secondary Accession NumbersNone
Natural Product Identification
Common Nameacefylline
DescriptionAcefylline belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Acefylline is an extremely weak basic (essentially neutral) compound (based on its pKa). acefylline is found in Pogostemon cablin. It acts as an adenosine receptor antagonist.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0231624 (acefylline)


  Mrv1572004221607022D          

 17 18  0  0  0  0            999 V2000
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
 10  4  2  0  0  0  0
 10  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  6  1  0  0  0  0
 14  5  2  0  0  0  0
 15  5  1  0  0  0  0
 16  8  2  0  0  0  0
 17  9  2  0  0  0  0
M  END
Download

3D MOL for NP0231624 (acefylline)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -2.5753   -2.0754   -0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8014   -0.9214   -0.3023 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731   -1.0477   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -2.1743   -0.1124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2744    0.0426    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707    1.2756    0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    2.1382    0.7842 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737    1.5348    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5624    0.2185    0.6532 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -0.7743    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2865   -0.9006   -0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259   -0.1824   -1.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117   -1.7920   -0.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866    1.3809    0.1396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    2.6793    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3837    0.2851   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261    0.3509   -0.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9230   -2.0154   -1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935   -3.0044   -0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4965   -2.1535   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    1.9600    1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113   -0.4872    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1977   -1.7885    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873   -1.6029   -0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196    2.7035   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2977    2.9498    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515    3.4008   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14  6  1  0
  6  5  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  9  8  1  0
  8  7  2  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  2 16  1  0
 16 17  2  0
 16 14  1  0
  7  6  1  0
 15 25  1  0
 15 26  1  0
 15 27  1  0
 10 22  1  0
 10 23  1  0
 13 24  1  0
  8 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
M  END
Download

3D SDF for NP0231624 (acefylline)


  Mrv1572004221607022D          

 17 18  0  0  0  0            999 V2000
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
 10  4  2  0  0  0  0
 10  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  6  1  0  0  0  0
 14  5  2  0  0  0  0
 15  5  1  0  0  0  0
 16  8  2  0  0  0  0
 17  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0231624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(N(CC(O)=O)C=N2)C(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10N4O4/c1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h4H,3H2,1-2H3,(H,14,15)

> <INCHI_KEY>
HCYFGRCYSCXKNQ-UHFFFAOYSA-N

> <FORMULA>
C9H10N4O4

> <MOLECULAR_WEIGHT>
238.203

> <EXACT_MASS>
238.070204818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.81266792857246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)acetic acid

> <ALOGPS_LOGP>
-0.80

> <JCHEM_LOGP>
-1.0676622833333338

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2622646839458302

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0357759017948838

> <JCHEM_POLAR_SURFACE_AREA>
95.74000000000001

> <JCHEM_REFRACTIVITY>
55.9158

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acefylline

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0231624 (acefylline)

Download
PDB for NP0231624 (acefylline)
HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.198   0.237   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -2.726   3.192   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.281   0.583   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    5   13                                                       
CONECT    4   10   13                                                       
CONECT    5    3   14   15                                                  
CONECT    6    7    8   13                                                  
CONECT    7    6   10   11                                                  
CONECT    8    6   12   16                                                  
CONECT    9   11   12   17                                                  
CONECT   10    4    7                                                       
CONECT   11    1    7    9                                                  
CONECT   12    2    8    9                                                  
CONECT   13    3    4    6                                                  
CONECT   14    5                                                            
CONECT   15    5                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

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3D PDB for NP0231624 (acefylline)
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SMILES for NP0231624 (acefylline)
CN1C2=C(N(CC(O)=O)C=N2)C(=O)N(C)C1=O
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INCHI for NP0231624 (acefylline)
InChI=1S/C9H10N4O4/c1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h4H,3H2,1-2H3,(H,14,15)
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View in JSmol
Synonyms
ValueSource
Theophylline-7-acetic acidMeSH
7-Theophyllineacetic acidMeSH
Acefylline, sodium saltMeSH
AcephyllineMeSH
AcefyllineMeSH
2-(1,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)acetateGenerator
Chemical FormulaC9H10N4O4
Average Mass238.2030 Da
Monoisotopic Mass238.07020 Da
IUPAC Name2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)acetic acid
Traditional Nameacefylline
CAS Registry NumberNot Available
SMILES
CN1C2=C(N(CC(O)=O)C=N2)C(=O)N(C)C1=O
InChI Identifier
InChI=1S/C9H10N4O4/c1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h4H,3H2,1-2H3,(H,14,15)
InChI KeyHCYFGRCYSCXKNQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pogostemon cablinLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassImidazopyrimidines  
Sub ClassPurines and purine derivatives  
Direct ParentXanthines  
Alternative Parents
Substituents
  • Xanthine
    • 

  • 6-oxopurine
    • 

  • Alpha-amino acid or derivatives
    • 

  • Purinone
    • 

  • Alkaloid or derivatives
    • 

  • Pyrimidone
    • 

  • Pyrimidine
    • 

  • N-substituted imidazole
    • 

  • Heteroaromatic compound
    • 

  • Azole
    • 

  • Imidazole
    • 

  • Vinylogous amide
    • 

  • Lactam
    • 

  • Urea
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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-0.8ALOGPS
logP-1.1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area95.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.92 m³·mol⁻¹ChemAxon
Polarizability21.81 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB13573  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcefylline  
METLIN IDNot Available
PubChem Compound69550  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]