NP-MRD: Showing NP-Card for (2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one (NP0191600)

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Record Information

Version

2.0

Created at

2022-09-04 08:37:29 UTC

Updated at

2022-09-04 08:37:29 UTC

NP-MRD ID

NP0191600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one

Description

Pterosin B belongs to the class of organic compounds known as indanones. Indanones are compounds containing an indane ring bearing a ketone group. (2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one is found in Microlepia strigosa, Pteridium aquilinum, Pteris bella, Pteris ensiformis, Pteris grevilleana and Pteris semipinnata. (2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one was first documented in 2020 (PMID: 32369939). Based on a literature review a small amount of articles have been published on Pterosin B (PMID: 34649082) (PMID: 31931331) (PMID: 34458862) (PMID: 33198253).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.1404   -2.3439   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474   -1.4417   -0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2514   -1.6980   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741   -0.8540   -0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578    0.2154    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654    0.4921    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046    1.6750    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3374   -0.3570    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430   -0.1310    0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2566    1.0346   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5922    1.2994    0.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1952    0.9260    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426    2.0837    1.0554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291    0.0243    0.2627 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5284    0.7660   -0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446   -0.9167   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685   -3.0373   -1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -1.7587   -1.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594   -2.9009   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4905   -2.5394   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6435    2.6321    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667    1.7666    2.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5054    1.4840    2.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    0.0778    1.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630   -1.0433    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355    0.7639   -1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.9571   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7622    2.2322   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5661   -0.5353    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    0.6635    0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125    0.2890   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505    1.8079   -0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300   -1.9829   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731   -0.6505   -1.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  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  0
 16 34  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
M  END


  Mrv1652309042210372D          

 16 17  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
    0.6411    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
   -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
   -0.6284    1.5229    0.0000 C   0  0  2  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
   -0.1435    0.8555    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  4 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191600

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O2/c1-8-6-11-7-9(2)14(16)13(11)10(3)12(8)4-5-15/h6,9,15H,4-5,7H2,1-3H3/t9-/m1/s1

> <INCHI_KEY>
SJNCSXMTBXDZQA-SECBINFHSA-N

> <FORMULA>
C14H18O2

> <MOLECULAR_WEIGHT>
218.296

> <EXACT_MASS>
218.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.364275555700402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.9276964979999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.15150351793765

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.850970495421702

> <JCHEM_PKA_STRONGEST_BASIC>
-2.415098349800215

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
65.95350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       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       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈O₂

Average Mass

218.2960 Da

Monoisotopic Mass

218.13068 Da

IUPAC Name

(2R)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydro-1H-inden-1-one

Traditional Name

(2R)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H18O2/c1-8-6-11-7-9(2)14(16)13(11)10(3)12(8)4-5-15/h6,9,15H,4-5,7H2,1-3H3/t9-/m1/s1

InChI Key

SJNCSXMTBXDZQA-SECBINFHSA-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
Microlepia strigosa	LOTUS Database	35616633
Pteridium aquilinum	LOTUS Database	35616633
Pteris bella	LOTUS Database	35616633
Pteris ensiformis	LOTUS Database	35616633
Pteris grevilleana	LOTUS Database	35616633
Pteris semipinnata	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
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	2.93	ChemAxon
pKa (Strongest Acidic)	15.85	ChemAxon
pKa (Strongest Basic)	-2.4	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	65.95 m³·mol⁻¹	ChemAxon
Polarizability	25.36 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029318

Chemspider ID

102965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ribeiro DDSF, Keller KM, Soto-Blanco B: Ptaquiloside and Pterosin B Levels in Mature Green Fronds and Sprouts of Pteridium arachnoideum. Toxins (Basel). 2020 May 1;12(5). pii: toxins12050288. doi: 10.3390/toxins12050288. [PubMed:32369939 ]
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 ]
Kisielius V, Lindqvist DN, Thygesen MB, Rodamer M, Hansen HCB, Rasmussen LH: Fast LC-MS quantification of ptesculentoside, caudatoside, ptaquiloside and corresponding pterosins in bracken ferns. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Feb 1;1138:121966. doi: 10.1016/j.jchromb.2019.121966. Epub 2020 Jan 3. [PubMed:31931331 ]
Rasmussen LH: Presence of the carcinogen ptaquiloside in fern-based food products and traditional medicine: Four cases of human exposure. Curr Res Food Sci. 2021 Aug 13;4:557-564. doi: 10.1016/j.crfs.2021.08.004. eCollection 2021. [PubMed:34458862 ]
Lee CY, Park HK, Lee BS, Jeong S, Hyun SA, Choi JW, Kim SW, Lee S, Lim S, Hwang KC: Novel Therapeutic Effects of Pterosin B on Ang II-Induced Cardiomyocyte Hypertrophy. Molecules. 2020 Nov 12;25(22):5279. doi: 10.3390/molecules25225279. [PubMed:33198253 ]
LOTUS database [Link]

Showing NP-Card for (2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one (NP0191600)

MOL for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D MOL for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D SDF for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D-SDF for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

PDB for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D PDB for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

SMILES for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

INCHI for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

Structure for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)

3D Structure for NP0191600 ((2r)-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydroinden-1-one)