NP-MRD: Showing NP-Card for 6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one (NP0237466)

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Record Information

Version

2.0

Created at

2022-09-06 20:36:40 UTC

Updated at

2022-09-06 20:36:40 UTC

NP-MRD ID

NP0237466

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one

Description

(S)-Pterosin K, also known as pterosin K, belongs to the class of organic compounds known as indanones. Indanones are compounds containing an indane ring bearing a ketone group (S)-Pterosin K is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (S)-Pterosin K has been detected, but not quantified in, green vegetables and root vegetables. 6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one is found in Pteridium aquilinum. This could make (S)-pterosin K a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.6697   -1.8809   -1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6266   -1.0423   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3155   -1.3820   -1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.6678   -0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276    0.3903    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999    0.7443    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    1.9139    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9399    0.0320   -0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3656    0.3420    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711   -0.6610    1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1636   -0.7242    2.7100 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6907    0.9811    0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8639    1.7665    1.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    0.4705   -0.2731 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9738    1.4795   -1.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0465    0.1959    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630   -0.7485    1.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2108   -0.8418   -0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8063   -2.8582   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -2.1693   -2.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415   -1.4171   -1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -2.2340   -1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    2.0721    2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039    1.8962    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889    2.8085    0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    0.3448   -0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270    1.3642    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0638   -0.4140    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -1.6923    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019    1.0412   -2.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179    2.0814   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668    2.2593   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7675   -0.2052   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    1.1404    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -1.6458    1.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911   -1.7044   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561   -1.0353   -1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 14 18  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8  2  1  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
M  END


  Mrv0541 05061309132D          

 18 19  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415    2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415    0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    0.1639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16  5  1  0  0  0  0
 17  8  1  0  0  0  0
 18 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0237466

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=C(C(=O)C(C)(CO)C2)C(C)=C1CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C15H19ClO2/c1-9-6-11-7-15(3,8-17)14(18)13(11)10(2)12(9)4-5-16/h6,17H,4-5,7-8H2,1-3H3

> <INCHI_KEY>
PIZARWYEACWLJN-UHFFFAOYSA-N

> <FORMULA>
C15H19ClO2

> <MOLECULAR_WEIGHT>
266.763

> <EXACT_MASS>
266.107357559

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.486838312928512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-2,3-dihydro-1H-inden-1-one

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
3.5575314993333325

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.94112489731478

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8245519699145154

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
75.28020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3H-inden-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.317   3.873   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.317   1.812   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       7.865   4.383   0.000  0.00  0.00          Cl+0
HETATM   17  O   UNK     0      -1.997   0.306   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5   12                                                       
CONECT    5    4   16                                                       
CONECT    6    9   11                                                       
CONECT    7   11   15                                                       
CONECT    8   15   17                                                       
CONECT    9    1    6   12                                                  
CONECT   10    2   12   13                                                  
CONECT   11    6    7   13                                                  
CONECT   12    4    9   10                                                  
CONECT   13   10   11   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15    3    7    8   14                                             
CONECT   16    5                                                            
CONECT   17    8                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Pterosin K	HMDB

Chemical Formula

C₁₅H₁₉ClO₂

Average Mass

266.7630 Da

Monoisotopic Mass

266.10736 Da

IUPAC Name

6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-2,3-dihydro-1H-inden-1-one

Traditional Name

6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3H-inden-1-one

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C(=O)C(C)(CO)C2)C(C)=C1CCCl

InChI Identifier

InChI=1S/C15H19ClO2/c1-9-6-11-7-15(3,8-17)14(18)13(11)10(2)12(9)4-5-16/h6,17H,4-5,7-8H2,1-3H3

InChI Key

PIZARWYEACWLJN-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
Pteridium aquilinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanones. Indanones are compounds containing an indane ring bearing a ketone group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Indanone
Aryl alkyl ketone
Aryl ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Alcohol
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	2.88	ALOGPS
logP	3.56	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.94	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.28 m³·mol⁻¹	ChemAxon
Polarizability	29.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036602

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015517

KNApSAcK ID

C00021504

Chemspider ID

4478771

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320787

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one (NP0237466)

MOL for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

3D MOL for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

3D SDF for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

3D-SDF for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

PDB for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

3D PDB for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

SMILES for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

INCHI for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

Structure for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)

3D Structure for NP0237466 (6-(2-chloroethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3h-inden-1-one)