NP-MRD: Showing NP-Card for 3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one (NP0169020)

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Record Information

Version

2.0

Created at

2022-09-03 04:54:34 UTC

Updated at

2022-09-03 04:54:34 UTC

NP-MRD ID

NP0169020

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one

Description

Lucidone belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. 3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one is found in Lindera erythrocarpa. 3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one was first documented in 2020 (PMID: 32344184). Based on a literature review a small amount of articles have been published on Lucidone (PMID: 35771834) (PMID: 35621756) (PMID: 35224793) (PMID: 34923886).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    5.9032   -0.6111   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900    0.6635   -0.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    0.6949   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2142    1.3830   -1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7622    1.1360   -0.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8832    1.6775   -1.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6880    0.2291    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956   -0.3686    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385   -1.1746    1.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122   -0.2630    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585    0.3896   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0277    0.3208   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455    1.0637   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1114    1.0288   -1.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8075    0.2522   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1110   -0.4821    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193   -0.4295    0.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851   -0.0249    0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966   -0.8461    1.5585 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6230   -1.0674   -1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4607   -1.2365    0.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9906   -0.5668   -0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947    2.0277   -1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921   -0.9002    1.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453    1.0027   -0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907    1.6746   -1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710    1.6035   -1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8861    0.2085   -0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5856   -1.0961    1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2263   -1.0277    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606   -0.5336    2.4455 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  7 18  2  0
 18 19  1  0
 18  3  1  0
 17 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
M  END


  Mrv1652309032206542D          

 19 20  0  0  0  0            999 V2000
    3.4656   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -2.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -4.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538   -4.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -5.2273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -4.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484   -5.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721   -4.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7571   -5.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775   -5.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9131   -4.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4282   -4.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -4.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -2.7666    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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  7 18  2  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169020

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(C(=O)\C=C\C2=CC=CC=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c1-19-13-9-12(17)14(15(13)18)11(16)8-7-10-5-3-2-4-6-10/h2-9,18H,1H3/b8-7+

> <INCHI_KEY>
ANPTXNYQLGJVRE-BQYQJAHWSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.257

> <EXACT_MASS>
256.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.71939326753831

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-4-methoxy-2-[(2E)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
2.0867067556666665

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.874715036805765

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889933457068377

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
74.41040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-methoxy-2-[(2E)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.469  -2.425   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.136  -3.195   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.136  -4.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.381  -5.640   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.906  -7.105   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.811  -8.351   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.366  -7.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.460  -8.351   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.087  -9.758   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.929  -8.190   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.024  -9.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.508  -9.275   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.413 -10.521   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.945 -10.360   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.571  -8.953   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.666  -7.707   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.134  -7.868   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.890  -5.640   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.425  -5.164   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    7    3   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2570 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

3-hydroxy-4-methoxy-2-[(2E)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one

Traditional Name

3-hydroxy-4-methoxy-2-[(2E)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(C(=O)\C=C\C2=CC=CC=C2)=C1O

InChI Identifier

InChI=1S/C15H12O4/c1-19-13-9-12(17)14(15(13)18)11(16)8-7-10-5-3-2-4-6-10/h2-9,18H,1H3/b8-7+

InChI Key

ANPTXNYQLGJVRE-BQYQJAHWSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Styrene
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Vinylogous acid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Cyclic ketone
Ketone
Enol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	1.83	ALOGPS
logP	2.09	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.41 m³·mol⁻¹	ChemAxon
Polarizability	26.72 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

C00007169

Chemspider ID

9428886

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11253859

PDB ID

Not Available

ChEBI ID

183569

Good Scents ID

Not Available

References

General References

Xu Q, Sheng CY: Lanostane triterpenoids from the fruiting bodies of Ganoderma hainanense and their cytotoxic activity. J Asian Nat Prod Res. 2023 Apr;25(4):342-348. doi: 10.1080/10286020.2022.2094787. Epub 2022 Jun 30. [PubMed:35771834 ]
Shin SW, Jeon JH, Kim JA, Park DS, Shin YJ, Oh HW: Inducible Expression of Several Drosophila melanogaster Genes Encoding Juvenile Hormone Binding Proteins by a Plant Diterpene Secondary Metabolite, Methyl Lucidone. Insects. 2022 Apr 29;13(5):420. doi: 10.3390/insects13050420. [PubMed:35621756 ]
Chen SY, Hsu YH, Wang SY, Chen YY, Hong CJ, Yen GC: Lucidone inhibits autophagy and MDR1 via HMGB1/RAGE/PI3K/Akt signaling pathway in pancreatic cancer cells. Phytother Res. 2022 Apr;36(4):1664-1677. doi: 10.1002/ptr.7385. Epub 2022 Feb 28. [PubMed:35224793 ]
Shi JX, Chen GY, Sun Q, Meng SY, Chi WQ: Antimicrobial lanostane triterpenoids from the fruiting bodies of Ganoderma applanatum. J Asian Nat Prod Res. 2022 Nov;24(11):1001-1007. doi: 10.1080/10286020.2021.2017899. Epub 2021 Dec 20. [PubMed:34923886 ]
Shi QQ, Huang YJ, Su HG, Gao Y, Lu SY, Peng XR, Li XN, Zhou L, Qiu MH: Structurally diverse lanostane triterpenoids from medicinal and edible mushroom Ganoderma resinaceum Boud. Bioorg Chem. 2020 Jul;100:103871. doi: 10.1016/j.bioorg.2020.103871. Epub 2020 Apr 22. [PubMed:32344184 ]
LOTUS database [Link]

Showing NP-Card for 3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one (NP0169020)

MOL for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

3D MOL for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

3D SDF for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

3D-SDF for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

PDB for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

3D PDB for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

SMILES for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

INCHI for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

Structure for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)

3D Structure for NP0169020 (3-hydroxy-4-methoxy-2-[(2e)-3-phenylprop-2-enoyl]cyclopenta-2,4-dien-1-one)