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Showing NP-Card for [({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid (NP0178889)

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Record Information
Version2.0
Created at2022-09-03 16:58:37 UTC
Updated at2022-09-03 16:58:38 UTC
NP-MRD IDNP0178889
Secondary Accession NumbersNone
Natural Product Identification
Common Name[({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid
Description7-[[(Carboxymethyl)(methyl)amino]methyl]-2-methyl-5,6-dihydroxy-4H-naphtho[2,3-b]pyran-4,8,9-trione belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Based on a literature review very few articles have been published on 7-[[(Carboxymethyl)(methyl)amino]methyl]-2-methyl-5,6-dihydroxy-4H-naphtho[2,3-b]pyran-4,8,9-trione.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)


  Mrv1652309032218582D          

 27 29  0  0  0  0            999 V2000
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 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 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 18 26  2  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
Download

3D MOL for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)

Download
3D SDF for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)

  Mrv1652309032218582D          

 27 29  0  0  0  0            999 V2000
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 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 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 18 26  2  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(CC(O)=O)CC1=C(O)C2=C(C=C3OC(C)=CC(=O)C3=C2O)C(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO8/c1-7-3-10(20)14-11(27-7)4-8-13(18(14)26)15(23)9(17(25)16(8)24)5-19(2)6-12(21)22/h3-4,23,26H,5-6H2,1-2H3,(H,21,22)

> <INCHI_KEY>
UXQPXYXSABKRLE-UHFFFAOYSA-N

> <FORMULA>
C18H15NO8

> <MOLECULAR_WEIGHT>
373.317

> <EXACT_MASS>
373.079766447

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.7392408433052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[({5,6-dihydroxy-2-methyl-4,8,9-trioxo-4H,8H,9H-cyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid

> <JCHEM_LOGP>
-1.6231562728816973

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.503643093711762

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.3699538210493549

> <JCHEM_PKA_STRONGEST_BASIC>
6.461904418129275

> <JCHEM_POLAR_SURFACE_AREA>
141.44

> <JCHEM_REFRACTIVITY>
95.03059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)
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PDB for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   18    9   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Download
3D PDB for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)
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SMILES for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)
CN(CC(O)=O)CC1=C(O)C2=C(C=C3OC(C)=CC(=O)C3=C2O)C(=O)C1=O
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INCHI for NP0178889 ([({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid)
InChI=1S/C18H15NO8/c1-7-3-10(20)14-11(27-7)4-8-13(18(14)26)15(23)9(17(25)16(8)24)5-19(2)6-12(21)22/h3-4,23,26H,5-6H2,1-2H3,(H,21,22)
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H15NO8
Average Mass373.3170 Da
Monoisotopic Mass373.07977 Da
IUPAC Name2-[({5,6-dihydroxy-2-methyl-4,8,9-trioxo-4H,8H,9H-cyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid
Traditional Name[({5,6-dihydroxy-2-methyl-4,8,9-trioxocyclohexa[g]chromen-7-yl}methyl)(methyl)amino]acetic acid
CAS Registry NumberNot Available
SMILES
CN(CC(O)=O)CC1=C(O)C2=C(C=C3OC(C)=CC(=O)C3=C2O)C(=O)C1=O
InChI Identifier
InChI=1S/C18H15NO8/c1-7-3-10(20)14-11(27-7)4-8-13(18(14)26)15(23)9(17(25)16(8)24)5-19(2)6-12(21)22/h3-4,23,26H,5-6H2,1-2H3,(H,21,22)
InChI KeyUXQPXYXSABKRLE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassNaphthopyrans  
Sub ClassNaphthopyranones  
Direct ParentNaphthopyranones  
Alternative Parents
Substituents
  • Naphthopyranone
    • 

  • Naphthoquinone
    • 

  • Chromone
    • 

  • 1-naphthol
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • Benzopyran
    • 

  • Naphthalene
    • 

  • 1-benzopyran
    • 

  • Quinone
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Cyclic ketone
    • 

  • Amino acid or derivatives
    • 

  • Ketone
    • 

  • Amino acid
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Enol
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Amine
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen 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-1.6ChemAxon
pKa (Strongest Acidic)0.37ChemAxon
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area141.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.03 m³·mol⁻¹ChemAxon
Polarizability35.74 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound53483341  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]