NP-MRD: Showing NP-Card for Linderone (NP0054855)

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Record Information

Version

2.0

Created at

2022-04-28 01:04:33 UTC

Updated at

2022-04-28 01:04:33 UTC

NP-MRD ID

NP0054855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Linderone

Description

Linderone belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Thus, linderone is considered to be a flavonoid. Linderone is found in Lindera erythrocarpa and Lindera pipericarpa. Linderone was first documented in 2013 (PMID: 32313803). Based on a literature review a small amount of articles have been published on Linderone (PMID: 31893611) (PMID: 29937519) (PMID: 24605879) (PMID: 23173924).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    5.2671    1.6268   -1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7989    0.6451   -0.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395    0.3772   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728   -0.6113    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7232   -1.5248    1.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011   -1.6873    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -0.6072    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7468   -1.4245    1.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    0.4836   -0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411    0.8609   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    1.9651   -1.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631    0.2154   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5628    0.6003   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8034   -0.0293   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077    0.5022   -0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2229   -0.0219   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2261   -1.1056    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -1.6439    1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -1.1049    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416    1.1128   -0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    2.0994   -1.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741    1.4031   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407    2.6086   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3744    1.6192   -1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4810   -2.4695    1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6901   -0.7624    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3193   -2.0195    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1878    1.8720   -2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2839   -0.6333    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173    1.4581   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9834    1.3574   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1359    0.4197   -0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2038   -1.5236    1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1458   -2.5024    1.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -1.5558    1.2094 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
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  2  0
 20  3  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END

  Mrv1652304282203042D          

 21 22  0  0  0  0            999 V2000
    0.1067   -2.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041   -4.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7907   -4.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112   -4.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4552   -5.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -5.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009   -6.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214   -6.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8569   -6.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3720   -7.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5515   -7.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160   -6.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5607   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454   -2.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -2.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303   -1.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  5 16  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(=O)C(=C(O)\C=C\C2=CC=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-15-13(18)12(14(19)16(15)21-2)11(17)9-8-10-6-4-3-5-7-10/h3-9,17H,1-2H3/b9-8+

> <INCHI_KEY>
IUTJITCLNLMFAJ-CMDGGOBGSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.70115952891885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-1-hydroxy-3-phenylprop-2-en-1-ylidene]-4,5-dimethoxycyclopent-4-ene-1,3-dione

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.833065681333333

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.468239980961308

> <JCHEM_PKA_STRONGEST_BASIC>
-4.725055829001117

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
81.20410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linderone

> <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       0.199  -4.735   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.445  -5.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.969  -7.105   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.874  -8.351   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.571  -7.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.476  -8.351   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.008  -8.190   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.850  -9.758   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.682  -9.919   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.308 -11.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.840 -11.486   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.466 -12.893   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.561 -14.139   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.029 -13.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.403 -12.571   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.047  -5.640   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.511  -5.164   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.910  -5.164   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.230  -3.658   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.199  -3.195   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
CONECT    1    2   16   20                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    5    1   17                                                  
CONECT   17   16                                                            
CONECT   18    2   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

2-[(2E)-1-hydroxy-3-phenylprop-2-en-1-ylidene]-4,5-dimethoxycyclopent-4-ene-1,3-dione

Traditional Name

linderone

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(=O)C(=C(O)\C=C\C2=CC=CC=C2)C1=O

InChI Identifier

InChI=1S/C16H14O5/c1-20-15-13(18)12(14(19)16(15)21-2)11(17)9-8-10-6-4-3-5-7-10/h3-9,17H,1-2H3/b9-8+

InChI Key

IUTJITCLNLMFAJ-CMDGGOBGSA-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
Lindera erythrocarpa	Plant	KNApSAcK
Lindera pipericarpa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
Vinylogous ester
Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120437 )

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	1.78	ALOGPS
logP	1.83	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.2 m³·mol⁻¹	ChemAxon
Polarizability	29.7 Å³	ChemAxon
Number of Rings	2	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

C00007167

Chemspider ID

10297676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Linderone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yoon JH, Pham TH, Lee J, Lee J, Ryu HW, Oh SR, Oh JW, Yoon DY: Methyl Linderone Suppresses TPA-Stimulated IL-8 and MMP-9 Expression Via the ERK/STAT3 Pathway in MCF-7 Breast Cancer Cells. J Microbiol Biotechnol. 2020 Mar 28;30(3):325-332. doi: 10.4014/jmb.1911.11068. [PubMed:31893611 ]
Song X, Liu C, Chen P, Zhang H, Sun R: Natural Product-Based Pesticide Discovery: Design, Synthesis and Bioactivity Studies of N-Amino-Maleimide Derivatives. Molecules. 2018 Jun 24;23(7). pii: molecules23071521. doi: 10.3390/molecules23071521. [PubMed:29937519 ]
Sevcikova Z, Pour M, Novak D, Ulrichova J, Vacek J: Chemical properties and biological activities of cyclopentenediones: a review. Mini Rev Med Chem. 2014 Apr;14(4):322-31. doi: 10.2174/1389557514666140306130207. [PubMed:24605879 ]
Xiao F, Liu W, Wang Y, Zhang Q, Li X, Hu X: Concise Synthesis of Linderaspirone A and Bi-linderone. Asian J Org Chem. 2013 Mar;2(3):216-219. doi: 10.1002/ajoc.201200184. Epub 2013 Jan 11. [PubMed:32313803 ]
Hosseinzadeh M, Hadi AH, Mohamad J, Khalilzadeh MA, Cheahd SC, Fadaeinasab M: Flavonoids and linderone from Lindera oxyphylla and their bioactivities. Comb Chem High Throughput Screen. 2013 Feb;16(2):160-6. [PubMed:23173924 ]

Showing NP-Card for Linderone (NP0054855)

MOL for NP0054855 (Linderone)

3D MOL for NP0054855 (Linderone)

3D SDF for NP0054855 (Linderone)

3D-SDF for NP0054855 (Linderone)

PDB for NP0054855 (Linderone)

3D PDB for NP0054855 (Linderone)

SMILES for NP0054855 (Linderone)

INCHI for NP0054855 (Linderone)

Structure for NP0054855 (Linderone)

3D Structure for NP0054855 (Linderone)