NP-MRD: Showing NP-Card for 2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid (NP0085610)

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Record Information

Version

1.0

Created at

2022-04-29 06:07:18 UTC

Updated at

2022-04-29 06:07:18 UTC

NP-MRD ID

NP0085610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid

Description

Pterosin E belongs to the class of organic compounds known as indanones. Indanones are compounds containing an indane ring bearing a ketone group. 2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid is found in Pteridium aquilinum . It was first documented in 2012 (PMID: 22587987). Based on a literature review a small amount of articles have been published on Pterosin E (PMID: 28936845) (PMID: 28532669) (PMID: 34649082) (PMID: 27177933).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -2.5764    2.2311   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872    1.3516   -0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579    1.9266   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    1.1483    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -0.2150   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832   -0.7824   -0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4729   -2.2363   -0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    0.0046   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077   -0.6550   -0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3364   -1.3158    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -0.5894    1.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270   -2.6546    0.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979   -0.7875    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913   -2.0018    0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601    0.3030   -0.0982 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4436    0.1016    0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059    1.5188    0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1696    2.2103    0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2184    3.3011   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744    2.0421   -1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581    2.9992    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1664   -2.5894   -1.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162   -2.7840    0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -2.5884   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    0.0817   -1.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -1.4132   -1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3053   -3.2684    1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    0.3768   -1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -0.5431    0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2474   -0.3607    1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9195    1.1051    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6947    2.4403   -0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    1.6428    1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17  4  1  0
  4  5  2  0
  5 13  1  0
 13 14  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  8  2  1  0
  2  1  1  0
  2  3  2  0
 13 15  1  0
  3  4  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 15 28  1  6
 17 32  1  0
 17 33  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
M  END


  Mrv1652304292208072D          

 17 18  0  0  1  0            999 V2000
    2.7845    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    0.6979    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
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  2  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
   -0.3984    2.9750    0.0000 O   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
    0.6411    1.9354    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
    1.3556    3.1729    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
    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
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  1  0  0  0
  4 10  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  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
M  END
> <DATABASE_ID>
NP0085610

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC2=C(C1=O)C(C)=C(CC(O)=O)C(C)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c1-7-4-10-5-8(2)14(17)13(10)9(3)11(7)6-12(15)16/h4,8H,5-6H2,1-3H3,(H,15,16)/t8-/m1/s1

> <INCHI_KEY>
UYEZJDNVWNIIKS-MRVPVSSYSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.279

> <EXACT_MASS>
232.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.27980807260541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2R)-2,4,6-trimethyl-3-oxo-2,3-dihydro-1H-inden-5-yl]acetic acid

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
3.0441333496666667

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.992424008520405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.259463193864906

> <JCHEM_PKA_STRONGEST_BASIC>
-7.524258573361632

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
65.6902

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-2,4,6-trimethyl-3-oxo-1,2-dihydroinden-5-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.531   2.073   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10    4    7   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₃

Average Mass

232.2790 Da

Monoisotopic Mass

232.10994 Da

IUPAC Name

2-[(2R)-2,4,6-trimethyl-3-oxo-2,3-dihydro-1H-inden-5-yl]acetic acid

Traditional Name

[(2R)-2,4,6-trimethyl-3-oxo-1,2-dihydroinden-5-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC2=C(C1=O)C(C)=C(CC(O)=O)C(C)=C2

InChI Identifier

InChI=1S/C14H16O3/c1-7-4-10-5-8(2)14(17)13(10)9(3)11(7)6-12(15)16/h4,8H,5-6H2,1-3H3,(H,15,16)/t8-/m1/s1

InChI Key

UYEZJDNVWNIIKS-MRVPVSSYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

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
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.35	ALOGPS
logP	3.04	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.69 m³·mol⁻¹	ChemAxon
Polarizability	25.28 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

C00055534

Chemspider ID

130981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

148588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang Y, Shi YS, Hu WZ, Song LY, Chen XZ: [Chemical constituents from Pteris multifida and cytotoxic activity]. Zhongguo Zhong Yao Za Zhi. 2016 Dec;41(24):4610-4614. doi: 10.4268/cjcmm20162420. [PubMed:28936845 ]
Kim JW, Kim HP, Sung SH: Cytotoxic pterosins from Pteris multifida roots against HCT116 human colon cancer cells. Bioorg Med Chem Lett. 2017 Jul 15;27(14):3144-3147. doi: 10.1016/j.bmcl.2017.05.034. Epub 2017 May 11. [PubMed:28532669 ]
Mrkajic NS, Hama JR, Strobel BW, Hansen HCB, Rasmussen LH, Pedersen AK, Christensen SCB, Hedegaard MJ: Removal of phytotoxins in filter sand used for drinking water treatment. Water Res. 2021 Oct 15;205:117610. doi: 10.1016/j.watres.2021.117610. Epub 2021 Aug 27. [PubMed:34649082 ]
Mohammad RH, Nur-E-Alam M, Lahmann M, Parveen I, Tizzard GJ, Coles SJ, Fowler M, Drake AF, Heyes D, Thoss V: Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome. Phytochemistry. 2016 Aug;128:82-94. doi: 10.1016/j.phytochem.2016.05.001. Epub 2016 May 10. [PubMed:27177933 ]
Lee YP, Hsu FL, Kang JJ, Chen CK, Lee SS: Metabolism of (2S)-pterosin A: identification of the phase I and phase II metabolites in rat urine. Drug Metab Dispos. 2012 Aug;40(8):1566-74. doi: 10.1124/dmd.112.045039. Epub 2012 May 15. [PubMed:22587987 ]

Showing NP-Card for 2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid (NP0085610)

MOL for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

3D MOL for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

3D SDF for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

3D-SDF for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

PDB for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

3D PDB for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

SMILES for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

INCHI for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

Structure for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)

3D Structure for NP0085610 (2,3-Dihydro-2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid)