NP-MRD: Showing NP-Card for 6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one (NP0176561)

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Record Information

Version

2.0

Created at

2022-09-03 14:14:53 UTC

Updated at

2022-09-03 14:14:53 UTC

NP-MRD ID

NP0176561

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one

Description

AC1LAV4F belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. 6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one is found in Cryptocarya kurzii. AC1LAV4F is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.6248   -0.8124    1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8563   -0.1914    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468    0.0525    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061   -0.3964    0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925   -0.1813    0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0669    0.4680   -0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4186    0.6247   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3659    0.1234    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9208   -0.5386    1.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5733   -0.6850    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2383    0.3076   -0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -0.0746    0.2746 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6895   -1.4427    0.4138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.4759   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0067    0.1465   -0.0034 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1248    0.6572   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.0530   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4808   -1.2226   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2886   -1.9106    0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3030   -3.0338    0.9467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744   -1.2508    0.2145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464    0.6017   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9287   -0.9333    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3346    0.8766   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7620    1.1431   -1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4294    0.2518   -0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6486   -0.9491    1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2403   -1.2041    2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1374    1.4045   -0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1932   -0.1048   -1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    0.4336    1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082   -1.8933   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675    0.0531   -1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5001    1.5745   -0.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0089    0.6323    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2610    1.7421   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8695    0.5705   -1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3539    0.3893   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4504   -1.7175    0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 12 11  1  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 21 15  1  0
 10  5  1  0
 13 32  1  0
 12 31  1  1
 14 33  1  0
 14 34  1  0
 15 35  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 11 29  1  0
 11 30  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
M  END


  Mrv1533004201505452D          

 21 22  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176561

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CC1CC=CC(=O)O1)CC(=O)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O4/c18-14(10-9-13-5-2-1-3-6-13)11-15(19)12-16-7-4-8-17(20)21-16/h1-6,8-10,15-16,19H,7,11-12H2

> <INCHI_KEY>
BAJICORABIZDNM-UHFFFAOYSA-N

> <FORMULA>
C17H18O4

> <MOLECULAR_WEIGHT>
286.327

> <EXACT_MASS>
286.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.2878633113766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.718722202333333

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.191875480342116

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.976667921063555

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8044200501456062

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
81.25180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4                                                       
CONECT   11    2   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₄

Average Mass

286.3270 Da

Monoisotopic Mass

286.12051 Da

IUPAC Name

6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

OC(CC1CC=CC(=O)O1)CC(=O)C=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H18O4/c18-14(10-9-13-5-2-1-3-6-13)11-15(19)12-16-7-4-8-17(20)21-16/h1-6,8-10,15-16,19H,7,11-12H2

InChI Key

BAJICORABIZDNM-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
Cryptocarya kurzii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Fatty alcohol
Styrene
Dihydropyranone
B'-hydroxy-alpha,beta-unsaturated-ketone
Monocyclic benzene moiety
Beta-hydroxy ketone
Fatty acyl
Benzenoid
Pyran
Acryloyl-group
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.1	ALOGPS
logP	2.72	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	81.25 m³·mol⁻¹	ChemAxon
Polarizability	30.29 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

495689

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-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one (NP0176561)

MOL for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

3D MOL for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

3D SDF for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

3D-SDF for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

PDB for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

3D PDB for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

SMILES for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

INCHI for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

Structure for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)

3D Structure for NP0176561 (6-(2-hydroxy-4-oxo-6-phenylhex-5-en-1-yl)-5,6-dihydropyran-2-one)