NP-MRD: Showing NP-Card for 2,4,7-trihydroxy-5-methoxyfluoren-9-one (NP0291666)

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Record Information

Version

2.0

Created at

2022-09-09 22:50:51 UTC

Updated at

2022-09-09 22:50:51 UTC

NP-MRD ID

NP0291666

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,7-trihydroxy-5-methoxyfluoren-9-one

Description

Denchrysan A belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. 2,4,7-trihydroxy-5-methoxyfluoren-9-one is found in Dendrobium chrysanthum. It was first documented in 2008 (PMID: 26065760). Based on a literature review very few articles have been published on Denchrysan A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.5673    2.7394    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    1.8798    0.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452    0.5125   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039   -0.0219   -0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472   -1.3813   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218   -1.9788   -0.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8430   -2.2018   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.6514   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160   -0.2807   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0339    0.0228    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036    1.2115    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641    2.4376    0.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1015    1.1764    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022    0.0085    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090   -0.0285    0.1295 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060   -1.1722   -0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7123   -1.1742   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7636   -2.2693   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0268   -3.4871   -0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409    2.3624    0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2707    3.7688    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    2.7889   -0.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    0.5837   -0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3259   -2.9619   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -3.2821   -0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    3.3057    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353    2.1149    0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7098   -0.8832    0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967   -2.1385   -0.0703 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9  3  1  0
 17 10  1  0
 18  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
M  END


  Mrv1652309102200502D          

 19 21  0  0  0  0            999 V2000
    3.1956   -1.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    2.3355    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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0291666

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC2=C1C1=C(O)C=C(O)C=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-19-11-5-7(16)3-9-13(11)12-8(14(9)18)2-6(15)4-10(12)17/h2-5,15-17H,1H3

> <INCHI_KEY>
DILPYVBUOBXTTA-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.229

> <EXACT_MASS>
258.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.248548423309465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,7-trihydroxy-5-methoxy-9H-fluoren-9-one

> <JCHEM_LOGP>
2.038211168666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.978665911000208

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.152215656415958

> <JCHEM_PKA_STRONGEST_BASIC>
-4.867965534488025

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
68.1176

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,4,7-trihydroxy-5-methoxyfluoren-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.965  -3.304   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.935  -2.159   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.410  -0.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.899   1.410   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.285  -2.159   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.679   1.410   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.610   2.820   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.610   4.360   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17    8   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
2,4,7-Trihydroxy-5-methoxy-9-fluorenone	MeSH

Chemical Formula

C₁₄H₁₀O₅

Average Mass

258.2290 Da

Monoisotopic Mass

258.05282 Da

IUPAC Name

2,4,7-trihydroxy-5-methoxy-9H-fluoren-9-one

Traditional Name

2,4,7-trihydroxy-5-methoxyfluoren-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC2=C1C1=C(O)C=C(O)C=C1C2=O

InChI Identifier

InChI=1S/C14H10O5/c1-19-11-5-7(16)3-9-13(11)12-8(14(9)18)2-6(15)4-10(12)17/h2-5,15-17H,1H3

InChI Key

DILPYVBUOBXTTA-UHFFFAOYSA-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
Dendrobium chrysanthum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Fluorenes

Sub Class

Not Available

Direct Parent

Fluorenes

Alternative Parents

Substituents

Fluorene
Anisole
Phenol ether
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketone
Ether
Polyol
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.04	ChemAxon
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.12 m³·mol⁻¹	ChemAxon
Polarizability	25.25 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

Not Available

Chemspider ID

21377079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71441453

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Y, Li Y, Qing C, Zhang Y, Wang L, Liu Y: 1,4,5-Trihydroxy-7-methoxy-9H-fluoren-9-one, a new cytotoxic compound from Dendrobium chrysotoxum. Food Chem. 2008 Jun 1;108(3):973-6. doi: 10.1016/j.foodchem.2007.12.007. Epub 2007 Dec 14. [PubMed:26065760 ]
LOTUS database [Link]

Showing NP-Card for 2,4,7-trihydroxy-5-methoxyfluoren-9-one (NP0291666)

MOL for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

3D MOL for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

3D SDF for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

3D-SDF for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

PDB for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

3D PDB for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

SMILES for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

INCHI for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

Structure for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)

3D Structure for NP0291666 (2,4,7-trihydroxy-5-methoxyfluoren-9-one)