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Showing NP-Card for Leptodactylone (NP0051450)

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Record Information
Version2.0
Created at2022-04-27 22:48:45 UTC
Updated at2022-04-27 22:48:45 UTC
NP-MRD IDNP0051450
Secondary Accession NumbersNone
Natural Product Identification
Common NameLeptodactylone
DescriptionLeptodactylone belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. Leptodactylone is found in Artemisia capillaris, Boenninghausenia sessilicarpa, Citrus medica, Leptodactylon californicum, Leptodactylon dianthiflorus and Linanthus dichotomus. Leptodactylone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051450 (Leptodactylone)


  Mrv1533004231520592D          

 16 17  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.4289    0.8250    0.0000 O   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
    2.1434   -0.4125    0.0000 C   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   -0.4125    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
Download

3D MOL for NP0051450 (Leptodactylone)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.2991   -1.8773    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8954   -0.5469    0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5838   -0.1184    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472   -1.0119   -0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7839   -0.6067   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8249   -1.5302   -0.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6305   -2.9081   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667    0.7333    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545    1.2340   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023    2.5943    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    3.4113    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    4.6653    0.1790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612    2.9351    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0324    1.6437    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035    1.2317    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3581    2.1034    0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3182   -1.9375    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949   -2.5144    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.2662   -1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7193   -2.0744   -0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009   -3.3761   -0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324   -3.3490    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -3.0999   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753    0.5383   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026    3.0098    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2195    3.1168    0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15  3  1  0
 14  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 16 26  1  0
M  END
Download

3D SDF for NP0051450 (Leptodactylone)


  Mrv1533004231520592D          

 16 17  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.4289    0.8250    0.0000 O   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
    2.1434   -0.4125    0.0000 C   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   -0.4125    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051450

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C=CC(=O)OC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O5/c1-14-7-5-8(15-2)10(13)11-6(7)3-4-9(12)16-11/h3-5,13H,1-2H3

> <INCHI_KEY>
TUFLVKBJDSZLAW-UHFFFAOYSA-N

> <FORMULA>
C11H10O5

> <MOLECULAR_WEIGHT>
222.196

> <EXACT_MASS>
222.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.09419302021879

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-5,7-dimethoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.8144517623333334

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.207874062640121

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4183888910390463

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
56.455900000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leptodactylone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0051450 (Leptodactylone)

Download
PDB for NP0051450 (Leptodactylone)
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0051450 (Leptodactylone)
Download
SMILES for NP0051450 (Leptodactylone)
COC1=CC(OC)=C2C=CC(=O)OC2=C1O
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INCHI for NP0051450 (Leptodactylone)
InChI=1S/C11H10O5/c1-14-7-5-8(15-2)10(13)11-6(7)3-4-9(12)16-11/h3-5,13H,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H10O5
Average Mass222.1960 Da
Monoisotopic Mass222.05282 Da
IUPAC Name8-hydroxy-5,7-dimethoxy-2H-chromen-2-one
Traditional Nameleptodactylone
CAS Registry NumberNot Available
SMILES
COC1=CC(OC)=C2C=CC(=O)OC2=C1O
InChI Identifier
InChI=1S/C11H10O5/c1-14-7-5-8(15-2)10(13)11-6(7)3-4-9(12)16-11/h3-5,13H,1-2H3
InChI KeyTUFLVKBJDSZLAW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia capillarisLOTUS Database
Boenninghausenia sessilicarpaPlant
Citrus medicaLOTUS Database
Leptodactylon californicumPlant
Leptodactylon dianthiflorusPlant
Linanthus dichotomusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassHydroxycoumarins  
Direct ParentHydroxycoumarins  
Alternative Parents
Substituents
  • Hydroxycoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.8ALOGPS
logP1.81ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.21ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.46 m³·mol⁻¹ChemAxon
Polarizability21.09 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 IDC00002479  
Chemspider IDNot Available
KEGG Compound IDC09271  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442134  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available