Np mrd loader

Showing NP-Card for chromene-2,2,6-triol (NP0249775)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-07 12:26:04 UTC
Updated at2022-09-07 12:26:04 UTC
NP-MRD IDNP0249775
Secondary Accession NumbersNone
Natural Product Identification
Common Namechromene-2,2,6-triol
Description2,2,6-Trihydroxychromene belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. chromene-2,2,6-triol is found in Artemisia annua. 2,2,6-Trihydroxychromene is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0249775 (chromene-2,2,6-triol)


  Mrv1533004261511172D          

 13 14  0  0  0  0            999 V2000
    0.0000   -1.6500    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   -0.4125    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 O   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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
M  END
Download

3D MOL for NP0249775 (chromene-2,2,6-triol)

     RDKit          3D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -3.9321    0.1600   -0.8409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6138   -0.1240   -0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112   -1.2392    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980   -1.5066    0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128   -0.6423    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2639    0.4682   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616    0.7037   -0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461    1.3426   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885    1.0964   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122   -0.0934    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0171    0.3021    1.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -0.8426   -0.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063   -0.8843    0.7234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5072    0.7375   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1371   -1.8844    0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288   -2.3951    1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7624    1.5792   -1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250    2.2226   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    1.7496   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3796    0.8732    2.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9740   -1.6234   -0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 13  1  0
 13 10  1  0
 10 11  1  0
 10 12  1  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  2  0
  7  2  1  0
  6  5  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
 11 20  1  0
 12 21  1  0
  9 19  1  0
  8 18  1  0
  7 17  1  0
M  END
Download

3D SDF for NP0249775 (chromene-2,2,6-triol)


  Mrv1533004261511172D          

 13 14  0  0  0  0            999 V2000
    0.0000   -1.6500    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   -0.4125    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 O   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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2OC(O)(O)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-1-2-8-6(5-7)3-4-9(11,12)13-8/h1-5,10-12H

> <INCHI_KEY>
JNEAWAJKXCLSEX-UHFFFAOYSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.159

> <EXACT_MASS>
180.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.953764639210007

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2H-chromene-2,2,6-triol

> <ALOGPS_LOGP>
0.29

> <JCHEM_LOGP>
1.1271717973333333

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.804570675250128

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.626177053991158

> <JCHEM_PKA_STRONGEST_BASIC>
-4.536313263159667

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
46.75500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chromene-2,2,6-triol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0249775 (chromene-2,2,6-triol)

Download
PDB for NP0249775 (chromene-2,2,6-triol)
HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.195   0.677   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.185  -1.037   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Download
3D PDB for NP0249775 (chromene-2,2,6-triol)
Download
SMILES for NP0249775 (chromene-2,2,6-triol)
OC1=CC=C2OC(O)(O)C=CC2=C1
Download
INCHI for NP0249775 (chromene-2,2,6-triol)
InChI=1S/C9H8O4/c10-7-1-2-8-6(5-7)3-4-9(11,12)13-8/h1-5,10-12H
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC9H8O4
Average Mass180.1590 Da
Monoisotopic Mass180.04226 Da
IUPAC Name2H-chromene-2,2,6-triol
Traditional Namechromene-2,2,6-triol
CAS Registry NumberNot Available
SMILES
OC1=CC=C2OC(O)(O)C=CC2=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-1-2-8-6(5-7)3-4-9(11,12)13-8/h1-5,10-12H
InChI KeyJNEAWAJKXCLSEX-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
Artemisia annuaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct Parent1-benzopyrans  
Alternative Parents
Substituents
  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Orthocarboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP0.29ALOGPS
logP1.13ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.76 m³·mol⁻¹ChemAxon
Polarizability16.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 Compound101681785  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]