NP-MRD: Showing NP-Card for 6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one (NP0262408)

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Record Information

Version

2.0

Created at

2022-09-08 05:11:46 UTC

Updated at

2022-09-08 05:11:46 UTC

NP-MRD ID

NP0262408

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    2.2397    2.4437    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978    1.4005    0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1251    1.7338   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0998    0.7802   -0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529   -0.5562    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5737   -0.9183    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607   -2.3638    0.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5508    0.0529    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9704   -0.2872    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818   -0.7271   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773   -1.0831   -0.2712 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900   -1.3235   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -2.5282   -0.2647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936   -0.3721    0.3029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4037   -0.7877   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5659    0.9164   -0.2994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1184    1.9716    0.3862 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    2.4303    1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039    2.4161   -0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    3.4412    0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3933    2.7827   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040   -2.7175    0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -2.9785    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453   -2.4830    1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0400   -1.1534    1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    0.5271    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985   -1.5919   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856    0.0902   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1585   -0.2451    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8686    0.1144   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1842   -1.5728   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0506   -1.1960    0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    0.9349   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7377    2.8492    0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 16  4  1  0
  4  5  2  0
  5 12  1  0
 12 13  2  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
  2  1  1  0
  2  3  2  0
 12 14  1  0
  3  4  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 14 29  1  1
 16 33  1  6
 17 34  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
M  END


  Mrv0541 05061310162D          

 17 18  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
   -1.4534    1.5229    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
    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
   -0.6284    1.5229    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    1.1104    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    0.8555    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
    4.2135    2.3479    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    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
  7  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  5  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0262408

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)C2=C(C1=O)C(C)=C(CCCl)C(C)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H17ClO2/c1-7-6-11-12(8(2)10(7)4-5-15)14(17)9(3)13(11)16/h6,9,13,16H,4-5H2,1-3H3

> <INCHI_KEY>
QKHXGZXWZRQICQ-UHFFFAOYSA-N

> <FORMULA>
C14H17ClO2

> <MOLECULAR_WEIGHT>
252.737

> <EXACT_MASS>
252.091707495

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.536021730812628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.2073847470000008

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.15924325197351

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.892114108596548

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2729037869693496

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.366

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-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      -2.713   2.843   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       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   3.613   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       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.268   1.597   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 Cl   UNK     0       7.865   4.383   0.000  0.00  0.00          Cl+0
HETATM   16  O   UNK     0      -0.744   0.132   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5   10                                                       
CONECT    5    4   15                                                       
CONECT    6    7   11                                                       
CONECT    7    1    6   10                                                  
CONECT    8    2   10   12                                                  
CONECT    9    3   13   14                                                  
CONECT   10    4    7    8                                                  
CONECT   11    6   12   13                                                  
CONECT   12    8   11   14                                                  
CONECT   13    9   11   16                                                  
CONECT   14    9   12   17                                                  
CONECT   15    5                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
6-(2-Chloroethyl)-2,3-dihydro-3-hydroxy-2,5,7-trimethyl-1H-inden-1-one	HMDB
6-(2-Chloroethyl)-3-hydroxy-2,5,7-trimethyl-1-indanone	HMDB

Chemical Formula

C₁₄H₁₇ClO₂

Average Mass

252.7370 Da

Monoisotopic Mass

252.09171 Da

IUPAC Name

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

Traditional Name

6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one

CAS Registry Number

Not Available

SMILES

CC1C(O)C2=C(C1=O)C(C)=C(CCCl)C(C)=C2

InChI Identifier

InChI=1S/C14H17ClO2/c1-7-6-11-12(8(2)10(7)4-5-15)14(17)9(3)13(11)16/h6,9,13,16H,4-5H2,1-3H3

InChI Key

QKHXGZXWZRQICQ-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
Pteris tremula	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
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.71	ALOGPS
logP	3.21	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-3.3	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	2	ChemAxon
Refractivity	70.37 m³·mol⁻¹	ChemAxon
Polarizability	27.54 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

HMDB0038161

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017391

KNApSAcK ID

C00021503

Chemspider ID

4478770

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320786

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)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one (NP0262408)

MOL for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D MOL for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D SDF for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D-SDF for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

PDB for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D PDB for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

SMILES for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

INCHI for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

Structure for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D Structure for NP0262408 (6-(2-chloroethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one)