NP-MRD: Showing NP-Card for Libanorin (NP0051451)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:48:46 UTC

Updated at

2022-04-27 22:48:46 UTC

NP-MRD ID

NP0051451

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Libanorin

Description

Libanorin belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Libanorin is found in Cicuta virosa, Diplotaenia damavandica, Libanotis schrenkiana and Peucedanum oreoselinum . Libanorin was first documented in 2017 (PMID: 27570117). Based on a literature review very few articles have been published on Libanorin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    5.1415    1.5472    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883    0.5767   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    0.1737   -1.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    0.1453    1.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -0.7920    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8613   -1.2052    2.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003   -1.2647   -0.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -2.1564   -0.2626 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5993   -2.3265   -1.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -3.5056    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344   -1.4850    0.1557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8132   -0.2193   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8726    0.3882    0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -0.1415    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5906    0.2791    2.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947    1.1900    2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7408    1.7099    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7324    2.6282    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8558    3.1321   -0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9533    2.6794   -1.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716    3.1452   -2.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0271    1.8118   -1.2656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8712    1.3010   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6211   -1.0412    1.4664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7445    2.5647    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7169    1.5139   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7817    1.1977    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643    0.7239   -2.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -0.9224   -1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423    0.4905   -1.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636    0.4790    2.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.9123   -2.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -2.7746   -1.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017   -1.2901   -2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048   -3.6084    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -4.2378   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0007   -3.8057    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3696   -2.1959   -0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1661   -0.4259   -1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    0.4281   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4692   -0.1351    3.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2855    1.5245    2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4212    2.9662    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6135    3.8490   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  8  7  1  6
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 23  2  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 24  1  0
 24 11  1  0
 14 13  1  0
 17 23  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 19 44  1  0
 18 43  1  0
 16 42  1  0
 15 41  1  0
M  END


  Mrv1652304282200482D          

 24 26  0  0  1  0            999 V2000
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0626    1.6514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7896    1.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8153    0.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908    1.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2178    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9190    1.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2436    0.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959    0.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    1.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)OC(C)(C)[C@@H]1CC2=C3OC(=O)C=CC3=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O5/c1-11(2)9-17(21)24-19(3,4)15-10-13-14(22-15)7-5-12-6-8-16(20)23-18(12)13/h5-9,15H,10H2,1-4H3/t15-/m0/s1

> <INCHI_KEY>
YCXXSERNLQPDHF-HNNXBMFYSA-N

> <FORMULA>
C19H20O5

> <MOLECULAR_WEIGHT>
328.364

> <EXACT_MASS>
328.131073744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.092997813717986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(8S)-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl]propan-2-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.7931416240000004

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.881880016273729

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
90.09560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
libanorin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.062   2.127   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.719  -0.076   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.141   2.271   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.450   3.083   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.807   2.355   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.855   0.815   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.116   3.166   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.473   2.438   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.782   3.249   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.521   0.899   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.952   0.962   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.330   3.580   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    3   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    2                                                       
CONECT   15   13   16   23   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15                                                            
CONECT   24   15                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₅

Average Mass

328.3640 Da

Monoisotopic Mass

328.13107 Da

IUPAC Name

2-[(8S)-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl]propan-2-yl 3-methylbut-2-enoate

Traditional Name

libanorin

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)OC(C)(C)[C@@H]1CC2=C3OC(=O)C=CC3=CC=C2O1

InChI Identifier

InChI=1S/C19H20O5/c1-11(2)9-17(21)24-19(3,4)15-10-13-14(22-15)7-5-12-6-8-16(20)23-18(12)13/h5-9,15H,10H2,1-4H3/t15-/m0/s1

InChI Key

YCXXSERNLQPDHF-HNNXBMFYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cicuta virosa	LOTUS Database	35616633
Diplotaenia damavandica	LOTUS Database	35616633
Libanotis schrenkiana	-	KNApSAcK
Peucedanum oreoselinum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

Angular furanocoumarin
Benzopyran
1-benzopyran
Coumaran
Alkyl aryl ether
Fatty acid ester
Pyranone
Pyran
Fatty acyl
Benzenoid
Enoate ester
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

furanocoumarin (CHEBI:6450 )
Furanocoumarins (C09272 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.75	ALOGPS
logP	3.79	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.1 m³·mol⁻¹	ChemAxon
Polarizability	35.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002480

Chemspider ID

390655

KEGG Compound ID

C09272

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Song PP, Zhao J, Liu ZL, Duan YB, Hou YP, Zhao CQ, Wu M, Wei M, Wang NH, Lv Y, Han ZJ: Evaluation of antifungal activities and structure-activity relationships of coumarin derivatives. Pest Manag Sci. 2017 Jan;73(1):94-101. doi: 10.1002/ps.4422. Epub 2016 Oct 3. [PubMed:27570117 ]

Showing NP-Card for Libanorin (NP0051451)

MOL for NP0051451 (Libanorin)

3D MOL for NP0051451 (Libanorin)

3D SDF for NP0051451 (Libanorin)

3D-SDF for NP0051451 (Libanorin)

PDB for NP0051451 (Libanorin)

3D PDB for NP0051451 (Libanorin)

SMILES for NP0051451 (Libanorin)

INCHI for NP0051451 (Libanorin)

Structure for NP0051451 (Libanorin)

3D Structure for NP0051451 (Libanorin)