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Showing NP-Card for leptorumol (NP0186754)

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Record Information
Version2.0
Created at2022-09-04 02:43:08 UTC
Updated at2022-09-04 02:43:08 UTC
NP-MRD IDNP0186754
Secondary Accession NumbersNone
Natural Product Identification
Common Nameleptorumol
DescriptionLeptorumol belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. leptorumol is found in Arachniodes miqueliana, Pisonia aculeata and Trianthema portulacastrum. leptorumol was first documented in 1968 (PMID: 5751282). Leptorumol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 23055639).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0186754 (leptorumol)


  Mrv1533004161518152D          

 15 16  0  0  0  0            999 V2000
    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
    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 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
    1.4289    0.8250    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
    3.5724   -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
    2.8579   -2.4750    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  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  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
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
Download

3D MOL for NP0186754 (leptorumol)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.7165   -1.4598   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4353   -0.7671   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.6220    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468    1.2655    0.1924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    1.3311    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847    2.8010    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9860    0.6848    0.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0934    1.4027    0.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2730    0.8485    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458   -0.5201   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077   -1.3101   -0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318   -2.5529   -0.3120 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913   -0.6691   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148   -1.3915   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -2.7653   -0.2741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.5532    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971   -1.1569    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650   -1.2097   -1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5031    0.7469    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737    3.1986   -0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    3.1051    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    3.2349    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935    1.4545    0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3014   -0.9870   -0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246   -3.3528   -0.3177 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
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14  2  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 15 25  1  0
M  END
Download

3D SDF for NP0186754 (leptorumol)


  Mrv1533004161518152D          

 15 16  0  0  0  0            999 V2000
    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
    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 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
    1.4289    0.8250    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
    3.5724   -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
    2.8579   -2.4750    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  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  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
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186754

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(C)=C2OC=CC(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O4/c1-5-9(13)6(2)11-8(10(5)14)7(12)3-4-15-11/h3-4,13-14H,1-2H3

> <INCHI_KEY>
OWGYZWMBXRFUQP-UHFFFAOYSA-N

> <FORMULA>
C11H10O4

> <MOLECULAR_WEIGHT>
206.197

> <EXACT_MASS>
206.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.279341109640516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-6,8-dimethyl-4H-chromen-4-one

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
2.7391926946666665

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.923471953172129

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.374626564286338

> <JCHEM_PKA_STRONGEST_BASIC>
-5.308870427115941

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
55.332300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-6,8-dimethylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0186754 (leptorumol)

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PDB for NP0186754 (leptorumol)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+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  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0186754 (leptorumol)
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SMILES for NP0186754 (leptorumol)
CC1=C(O)C(C)=C2OC=CC(=O)C2=C1O
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INCHI for NP0186754 (leptorumol)
InChI=1S/C11H10O4/c1-5-9(13)6(2)11-8(10(5)14)7(12)3-4-15-11/h3-4,13-14H,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H10O4
Average Mass206.1970 Da
Monoisotopic Mass206.05791 Da
IUPAC Name5,7-dihydroxy-6,8-dimethyl-4H-chromen-4-one
Traditional Name5,7-dihydroxy-6,8-dimethylchromen-4-one
CAS Registry NumberNot Available
SMILES
CC1=C(O)C(C)=C2OC=CC(=O)C2=C1O
InChI Identifier
InChI=1S/C11H10O4/c1-5-9(13)6(2)11-8(10(5)14)7(12)3-4-15-11/h3-4,13-14H,1-2H3
InChI KeyOWGYZWMBXRFUQP-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
Leptorumohra miquelianaLOTUS Database
Pisonia aculeataLOTUS Database
Trianthema portulacastrumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct ParentChromones  
Alternative Parents
Substituents
  • Chromone
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.78ALOGPS
logP2.74ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)7.37ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.33 m³·mol⁻¹ChemAxon
Polarizability20.28 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 CompoundNot Available
PDB IDNot Available
ChEBI ID67370  
Good Scents IDNot Available
References
General References
  1. Shivhare MK, Singour PK, Chaurasiya PK, Pawar RS: Trianthema portulacastrum Linn. (Bishkhapra). Pharmacogn Rev. 2012 Jul;6(12):132-40. doi: 10.4103/0973-7847.99947. [PubMed:23055639  ] 
  2. Fukushima S, Noro T, Saiki Y, Ueno A, Akahori Y: [Studies on the constituents of Leptorumohra miqueliana H Ito. I. The structures of leptorumolin and leptorumol]. Yakugaku Zasshi. 1968 Sep;88(9):1135-42. doi: 10.1248/yakushi1947.88.9_1135. [PubMed:5751282  ] 
  3. LOTUS database [Link]