NP-MRD: Showing NP-Card for Methyllucidone (NP0054858)

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Record Information

Version

2.0

Created at

2022-04-28 01:04:40 UTC

Updated at

2022-04-28 01:04:41 UTC

NP-MRD ID

NP0054858

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyllucidone

Description

Methyllucidone belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Thus, methyllucidone is considered to be a flavonoid. Methyllucidone is found in Lindera erythrocarpa and Lindera lucida. Methyllucidone was first documented in 2005 (PMID: 16055336). Based on a literature review very few articles have been published on Methyllucidone (PMID: 29456111).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    5.4988   -0.7245    3.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7799   -1.5094    2.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4590   -1.1834    1.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3958   -1.2972    2.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740   -0.8586    1.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0063   -0.8525    2.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -0.4392    0.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844    0.0312   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678    0.2103   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897    0.6861   -1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8195    0.8781   -1.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980    1.3848   -2.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562    1.5914   -2.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6250    1.3075   -1.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9638    0.8022   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5792    0.5932   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4258    0.3705   -1.5847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511   -0.6293   -2.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0216   -0.6480    0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422   -0.3931   -0.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9390   -0.7710    4.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5077    0.3490    2.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4766   -1.1587    3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332   -1.6708    3.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503   -0.0497    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    0.9309   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453    1.6237   -3.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753    1.9879   -3.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6923    1.4622   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4854    0.5563    0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1071    0.1912    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.9330   -2.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.5610   -2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9827   -0.2772   -3.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8  7  2  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 19  1  0
 19 20  2  0
 16 11  1  0
 19  7  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
  4 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652304282203042D          

 20 21  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
   -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
   -1.6112   -4.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961   -5.0548    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
    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
  7  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 17  1  0  0  0  0
  1 17  1  0  0  0  0
 17 18  2  0  0  0  0
  1 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054858

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-19-13(9-8-11-6-4-3-5-7-11)15-12(17)10-14(20-2)16(15)18/h3-10H,1-2H3/b9-8+,15-13-

> <INCHI_KEY>
FITVJPYUOAZKPN-PBMBQWDMSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.284

> <EXACT_MASS>
270.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.432259242831883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-4-methoxy-2-[(2E)-1-methoxy-3-phenylprop-2-en-1-ylidene]cyclopent-4-ene-1,3-dione

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.3517233626666663

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.592659187304455

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
79.23670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyllucidone

> <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  C   UNK     0      -0.850  -9.758   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.682  -9.919   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.308 -11.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.840 -11.486   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.466 -12.893   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.561 -14.139   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.029 -13.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.403 -12.571   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.008  -8.190   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.913  -9.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.047  -5.640   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.511  -5.164   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.199  -3.195   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
CONECT    1    2   17   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    6   16                                                       
CONECT   16   15                                                            
CONECT   17    5    1   18                                                  
CONECT   18   17                                                            
CONECT   19    1   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2840 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

(2Z)-4-methoxy-2-[(2E)-1-methoxy-3-phenylprop-2-en-1-ylidene]cyclopent-4-ene-1,3-dione

Traditional Name

methyllucidone

CAS Registry Number

Not Available

SMILES

CO\C(\C=C\C1=CC=CC=C1)=C1\C(=O)C=C(OC)C1=O

InChI Identifier

InChI=1S/C16H14O4/c1-19-13(9-8-11-6-4-3-5-7-11)15-12(17)10-14(20-2)16(15)18/h3-10H,1-2H3/b9-8+,15-13-

InChI Key

FITVJPYUOAZKPN-PBMBQWDMSA-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 lucida	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
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120440 )

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	2.39	ALOGPS
logP	2.35	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.24 m³·mol⁻¹	ChemAxon
Polarizability	28.43 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

C00007170

Chemspider ID

10297680

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21680425

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jin Y, Kim YH, Park JY, Lee YJ, Oh HM, Choi SK, Han DC, Kwon BM: Methyllucidone inhibits STAT3 activity by regulating the expression of the protein tyrosine phosphatase MEG2 in DU145 prostate carcinoma cells. Bioorg Med Chem Lett. 2018 Mar 1;28(5):853-857. doi: 10.1016/j.bmcl.2018.02.012. Epub 2018 Feb 8. [PubMed:29456111 ]
Oh HM, Choi SK, Lee JM, Lee SK, Kim HY, Han DC, Kim HM, Son KH, Kwon BM: Cyclopentenediones, inhibitors of farnesyl protein transferase and anti-tumor compounds, isolated from the fruit of Lindera erythrocarpa Makino. Bioorg Med Chem. 2005 Nov 15;13(22):6182-7. doi: 10.1016/j.bmc.2005.06.029. Epub 2005 Aug 1. [PubMed:16055336 ]

Showing NP-Card for Methyllucidone (NP0054858)

MOL for NP0054858 (Methyllucidone)

3D MOL for NP0054858 (Methyllucidone)

3D SDF for NP0054858 (Methyllucidone)

3D-SDF for NP0054858 (Methyllucidone)

PDB for NP0054858 (Methyllucidone)

3D PDB for NP0054858 (Methyllucidone)

SMILES for NP0054858 (Methyllucidone)

INCHI for NP0054858 (Methyllucidone)

Structure for NP0054858 (Methyllucidone)

3D Structure for NP0054858 (Methyllucidone)