NP-MRD: Showing NP-Card for 1-Phenylpropan-2-one (NP0006780)

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Record Information

Version

1.0

Created at

2020-12-09 03:42:44 UTC

Updated at

2021-08-19 23:59:42 UTC

NP-MRD ID

NP0006780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Phenylpropan-2-one

Provided By

NPAtlas

Description

Phenylacetone belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 1-Phenylpropan-2-one is found in Gossypium hirsutum and Streptomyces. It was first documented in 1998 (PMID: 9682156). Based on a literature review a significant number of articles have been published on Phenylacetone (PMID: 17193176) (PMID: 34204515) (PMID: 33787141) (PMID: 32808530).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118353D          

 20 20  0  0  0  0            999 V2000
    3.4062   -0.0448    0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9448   -0.2419    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115   -0.9858    1.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    0.5212   -0.5567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4003    0.2292   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1239    0.9583    0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351    0.7002    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0771   -0.3329    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4018   -1.0923   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648   -0.8007   -0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    0.9075   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621   -0.9271   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495    0.0143    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2543    0.2899   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612    1.6091   -0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.7681    1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9866    1.2819    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200   -0.5291    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321   -1.8973   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -1.4279   -1.6150 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
 10 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3

> <INCHI_KEY>
QCCDLTOVEPVEJK-UHFFFAOYSA-N

> <FORMULA>
C9H10O

> <MOLECULAR_WEIGHT>
134.178

> <EXACT_MASS>
134.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.1498113320868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-phenylpropan-2-one

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.9406196279999999

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.91852722765383

> <JCHEM_PKA_STRONGEST_BASIC>
-7.3710093943027335

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
40.916700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.406  -0.045   0.121  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.945  -0.242   0.326  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.512  -0.986   1.168  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.024   0.521  -0.557  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.400   0.229  -0.244  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.124   0.958   0.681  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.435   0.700   0.979  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.077  -0.333   0.334  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.402  -1.092  -0.598  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.065  -0.801  -0.877  0.00  0.00           C+0
HETATM   11  H   UNK     0       3.620   0.908  -0.408  0.00  0.00           H+0
HETATM   12  H   UNK     0       3.762  -0.927  -0.460  0.00  0.00           H+0
HETATM   13  H   UNK     0       3.950   0.014   1.087  0.00  0.00           H+0
HETATM   14  H   UNK     0       1.254   0.290  -1.630  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.261   1.609  -0.379  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.607   1.768   1.181  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.987   1.282   1.706  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.120  -0.529   0.578  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.932  -1.897  -1.089  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.585  -1.428  -1.615  0.00  0.00           H+0
CONECT    1    2   11   12   13                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14   15                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9    5   20                                                  
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    4                                                            
CONECT   15    4                                                            
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   10                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1-Phenyl-2-propanone	ChEBI
3-Phenyl-2-propanone	ChEBI
Benzyl methyl ketone	ChEBI
Methyl benzyl ketone	ChEBI
Phenyl-2-propanone	ChEBI
Phenylmethyl methyl ketone	ChEBI

Chemical Formula

C₉H₁₀O

Average Mass

134.1780 Da

Monoisotopic Mass

134.07316 Da

IUPAC Name

1-phenylpropan-2-one

Traditional Name

phenylacetone

CAS Registry Number

Not Available

SMILES

CC(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3

InChI Key

QCCDLTOVEPVEJK-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, 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
Gossypium hirsutum	LOTUS Database	35616633
Streptomyces	NPAtlas	17193176

Species Where Detected

Species Name	Source	Reference
Streptomyces microflavus No.2445	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methyl ketone (CHEBI:52052 )
propanone (CHEBI:52052 )
a small molecule (CPD-7233 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	214.00 to 217.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	5213 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.440	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.7	ALOGPS
logP	1.94	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	15.92	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.92 m³·mol⁻¹	ChemAxon
Polarizability	15.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA018784

HMDB ID

HMDB0061970

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Phenylacetone

METLIN ID

Not Available

PubChem Compound

7678

PDB ID

Not Available

ChEBI ID

52052

Good Scents ID

rw1412311

References

General References

Dickschat JS, Martens T, Brinkhoff T, Simon M, Schulz S: Volatiles released by a Streptomyces species isolated from the North Sea. Chem Biodivers. 2005 Jul;2(7):837-65. doi: 10.1002/cbdv.200590062. [PubMed:17193176 ]
Tarjanyi Z, Kalasz H, Szebeni G, Hollosi I, Bathori M, Furst S: Gas-chromatographic study on the stereoselectivity of deprenyl metabolism. J Pharm Biomed Anal. 1998 Aug;17(4-5):725-31. doi: 10.1016/s0731-7085(97)00227-6. [PubMed:9682156 ]
Purwani NN, Martin C, Savino S, Fraaije MW: Modular Assembly of Phosphite Dehydrogenase and Phenylacetone Monooxygenase for Tuning Cofactor Regeneration. Biomolecules. 2021 Jun 17;11(6). pii: biom11060905. doi: 10.3390/biom11060905. [PubMed:34204515 ]
Wei RR, Ma QG, Sang ZP, Dong JH: [Studies on phenylpropanoids from Eleocharis dulcis and their hepatoprotective activities]. Zhongguo Zhong Yao Za Zhi. 2021 Mar;46(6):1430-1437. doi: 10.19540/j.cnki.cjcmm.20200821.201. [PubMed:33787141 ]
Wang C, Wu L, Xu W, He F, Qu J, Chen Y: Palladium-Catalyzed Secondary Benzylic Imidoylative Reactions. Org Lett. 2020 Sep 4;22(17):6954-6959. doi: 10.1021/acs.orglett.0c02515. Epub 2020 Aug 18. [PubMed:32808530 ]

Showing NP-Card for 1-Phenylpropan-2-one (NP0006780)

MOL for NP0006780 (1-Phenylpropan-2-one)

3D MOL for NP0006780 (1-Phenylpropan-2-one)

3D SDF for NP0006780 (1-Phenylpropan-2-one)

3D-SDF for NP0006780 (1-Phenylpropan-2-one)

PDB for NP0006780 (1-Phenylpropan-2-one)

3D PDB for NP0006780 (1-Phenylpropan-2-one)

SMILES for NP0006780 (1-Phenylpropan-2-one)

INCHI for NP0006780 (1-Phenylpropan-2-one)

Structure for NP0006780 (1-Phenylpropan-2-one)

3D Structure for NP0006780 (1-Phenylpropan-2-one)