NP-MRD: Showing NP-Card for methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate (NP0217518)

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Record Information

Version

2.0

Created at

2022-09-05 17:53:29 UTC

Updated at

2022-09-05 17:53:30 UTC

NP-MRD ID

NP0217518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate

Description

Methyl 5-hydroxy-7-p-hydroxyphenysl-3-keto-4Z,6E-heptadienoate belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate is found in Phaeolepiota aurea. Based on a literature review very few articles have been published on methyl 5-hydroxy-7-p-hydroxyphenysl-3-keto-4Z,6E-heptadienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    7.0114    0.3808   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6105    0.3714   -1.3511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9084   -0.6256   -0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138   -1.5802   -0.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223   -0.5349   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544   -0.0138    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7876    0.2943    1.5382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458    0.1415    0.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5844   -0.1502    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8833   -0.6495   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8088    0.0720    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8291   -0.1915   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2334   -0.0157    0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2243   -0.3375   -0.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5385   -0.1611   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9135    0.3409    0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2526    0.5168    1.0155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9504    0.6712    1.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6181    0.4832    1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4036   -0.4144   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5099    0.3460   -0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2749    1.3557   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409    0.1503   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867   -1.5366   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    0.5388    1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4007   -1.4072   -1.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180    0.4631    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624   -0.5907   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8997   -0.7302   -1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3327   -0.4132   -1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7246    1.4053    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2707    1.0574    2.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082    0.7636    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652309052219532D          

 19 19  0  0  0  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    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
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC(=O)\C=C(/O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O5/c1-19-14(18)9-13(17)8-12(16)7-4-10-2-5-11(15)6-3-10/h2-8,15-16H,9H2,1H3/b7-4+,12-8-

> <INCHI_KEY>
CSKXJOXKPFXJNS-JHLWKMQHSA-N

> <FORMULA>
C14H14O5

> <MOLECULAR_WEIGHT>
262.261

> <EXACT_MASS>
262.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.70322037934939

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4Z,6E)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate

> <JCHEM_LOGP>
2.056637737333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.500932193938102

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.840945241757069

> <JCHEM_PKA_STRONGEST_BASIC>
-5.312593916006628

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
71.91600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4Z,6E)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -8.470   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000 -10.780   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667 -10.780   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -8.470   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  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Methyl 5-hydroxy-7-p-hydroxyphenysl-3-keto-4Z,6E-heptadienoic acid	Generator

Chemical Formula

C₁₄H₁₄O₅

Average Mass

262.2610 Da

Monoisotopic Mass

262.08412 Da

IUPAC Name

methyl (4Z,6E)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate

Traditional Name

methyl (4Z,6E)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC(=O)\C=C(/O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C14H14O5/c1-19-14(18)9-13(17)8-12(16)7-4-10-2-5-11(15)6-3-10/h2-8,15-16H,9H2,1H3/b7-4+,12-8-

InChI Key

CSKXJOXKPFXJNS-JHLWKMQHSA-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
Phaeolepiota aurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
1-hydroxy-2-unsubstituted benzenoid
Beta-keto acid
Fatty acid methyl ester
Phenol
Fatty acid ester
Fatty acyl
1,3-dicarbonyl compound
Keto acid
Acryloyl-group
Vinylogous acid
Alpha,beta-unsaturated ketone
Methyl ester
Enone
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Enol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.06	ChemAxon
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.92 m³·mol⁻¹	ChemAxon
Polarizability	26.7 Å³	ChemAxon
Number of Rings	1	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

78435751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate (NP0217518)

MOL for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

3D MOL for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

3D SDF for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

3D-SDF for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

PDB for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

3D PDB for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

SMILES for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

INCHI for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

Structure for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)

3D Structure for NP0217518 (methyl (4z,6e)-5-hydroxy-7-(4-hydroxyphenyl)-3-oxohepta-4,6-dienoate)