NP-MRD: Showing NP-Card for methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate (NP0189616)

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Record Information

Version

2.0

Created at

2022-09-04 06:07:24 UTC

Updated at

2022-09-04 06:07:24 UTC

NP-MRD ID

NP0189616

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate

Description

(+)-Applanatumol Z belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate is found in Ganoderma applanatum. Based on a literature review very few articles have been published on (+)-applanatumol Z.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.8142    2.9905    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711    1.7477    1.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7403    1.0592    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976    1.6397   -0.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599   -0.2056   -0.1107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3404   -1.3626    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389   -2.4376    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128   -1.6913   -0.9626 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1988   -1.8271   -2.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289   -0.2208   -0.5942 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1490    0.0623    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576    0.2049    1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627    0.1980    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882    0.4187    1.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8380    0.5358    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429    0.7530    2.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506    0.4353   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4858    0.2197   -1.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1173    0.1065   -1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3303   -0.1045   -2.2187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9965    3.0316    2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118    3.0734    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2214    3.8482    1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8528   -0.5063   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -1.6141    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311   -1.2364    1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3906   -2.9701   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474   -3.0980    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -2.1030   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -2.3889   -2.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6980    0.4528   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    0.5019    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1932   -0.0020    2.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    0.5253   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677    0.1381   -2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030   -0.1742   -3.1295 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 10  5  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  6
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 10 31  1  6
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END


  Mrv1652309042208072D          

 20 21  0  0  1  0            999 V2000
   -1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0597   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -2.5687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5052   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752   -1.7840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6729   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5014   -2.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -4.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4575   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -1.0192    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
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189616

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1CC[C@@H](O)[C@@H]1C(=O)C1=CC(O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O6/c1-20-14(19)8-3-5-11(17)12(8)13(18)9-6-7(15)2-4-10(9)16/h2,4,6,8,11-12,15-17H,3,5H2,1H3/t8-,11-,12-/m1/s1

> <INCHI_KEY>
SXPHWVWHKNUWLH-GGZOMVNGSA-N

> <FORMULA>
C14H16O6

> <MOLECULAR_WEIGHT>
280.276

> <EXACT_MASS>
280.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.162056584679

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,3R)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate

> <JCHEM_LOGP>
1.3805237463333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.01218526682918

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.188750496946595

> <JCHEM_PKA_STRONGEST_BASIC>
-2.915074679409619

> <JCHEM_POLAR_SURFACE_AREA>
104.05999999999999

> <JCHEM_REFRACTIVITY>
69.5483

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,3R)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.468   1.425   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.468  -0.115   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.199  -0.115   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.111  -3.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.364  -4.795   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.904  -4.795   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.810  -6.041   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.380  -3.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.845  -2.854   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.165  -1.348   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.989  -3.885   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.669  -5.391   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.814  -6.422   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.494  -7.928   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -7.278  -5.946   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.599  -4.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.454  -3.409   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.774  -1.903   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   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

C₁₄H₁₆O₆

Average Mass

280.2760 Da

Monoisotopic Mass

280.09469 Da

IUPAC Name

methyl (1R,2R,3R)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate

Traditional Name

methyl (1R,2R,3R)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1CC[C@@H](O)[C@@H]1C(=O)C1=CC(O)=CC=C1O

InChI Identifier

InChI=1S/C14H16O6/c1-20-14(19)8-3-5-11(17)12(8)13(18)9-6-7(15)2-4-10(9)16/h2,4,6,8,11-12,15-17H,3,5H2,1H3/t8-,11-,12-/m1/s1

InChI Key

SXPHWVWHKNUWLH-GGZOMVNGSA-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
Ganoderma applanatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aryl alkyl ketone
Hydroquinone
Gamma-keto acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Keto acid
Cyclopentanol
Monocyclic benzene moiety
Vinylogous acid
Methyl ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
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	1.38	ChemAxon
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.55 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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

Not Available

Chemspider ID

78440839

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584171

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate (NP0189616)

MOL for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

3D MOL for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

3D SDF for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

3D-SDF for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

PDB for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

3D PDB for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

SMILES for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

INCHI for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

Structure for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)

3D Structure for NP0189616 (methyl (1r,2r,3r)-2-(2,5-dihydroxybenzoyl)-3-hydroxycyclopentane-1-carboxylate)