NP-MRD: Showing NP-Card for methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate (NP0289742)

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Record Information

Version

2.0

Created at

2022-09-09 20:04:41 UTC

Updated at

2022-09-09 20:04:42 UTC

NP-MRD ID

NP0289742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate

Description

Phomarosine C belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate is found in Phoma herbarum. Based on a literature review very few articles have been published on Phomarosine C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
   -0.1387   -4.4222   -2.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189   -3.2800   -1.3272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273   -2.4813   -1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3338   -2.7292   -2.0155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -1.2633   -0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -0.4847   -0.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5941    0.7142    0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4499    0.8154    1.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    1.9805    2.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8633    3.1341    1.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    4.3103    2.4925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0244    3.1091    0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8923    1.9187   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745   -0.9569    0.3573 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -0.6919   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.7378   -1.5255 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1515   -0.3738    0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550   -0.3287    1.7908 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4602   -0.1007   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272    0.2070    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3310    0.9802   -1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -4.1335   -3.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9841   -5.1310   -2.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -5.0335   -1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2476   -0.7986   -1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450   -0.0711    2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417    1.9872    3.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1920    5.1642    2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2532    4.0542   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    1.9104   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -0.9347    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340   -1.0415   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3532    0.7957    0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9560   -0.7574    1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.8102    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373    0.6506   -2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9700    1.8498   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2749    1.3600   -1.1965 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 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 14 31  1  0
 19 32  1  0
 20 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
M  END


  Mrv1652309092222042D          

 21 21  0  0  0  0            999 V2000
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
  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  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 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289742

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H17NO5/c1-9(2)13(18)14(19)16-12(15(20)21-3)8-10-4-6-11(17)7-5-10/h4-9,17H,1-3H3,(H,16,19)/b12-8-

> <INCHI_KEY>
SPJBROGNNHNGFF-WQLSENKSSA-N

> <FORMULA>
C15H17NO5

> <MOLECULAR_WEIGHT>
291.303

> <EXACT_MASS>
291.110672651

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.868197563599345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate

> <JCHEM_LOGP>
2.407498131333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.776264255904001

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.889369237510357

> <JCHEM_PKA_STRONGEST_BASIC>
-6.364645530877568

> <JCHEM_POLAR_SURFACE_AREA>
92.7

> <JCHEM_REFRACTIVITY>
77.426

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   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   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    5   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₇NO₅

Average Mass

291.3030 Da

Monoisotopic Mass

291.11067 Da

IUPAC Name

methyl (2Z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate

Traditional Name

methyl (2Z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H17NO5/c1-9(2)13(18)14(19)16-12(15(20)21-3)8-10-4-6-11(17)7-5-10/h4-9,17H,1-3H3,(H,16,19)/b12-8-

InChI Key

SPJBROGNNHNGFF-WQLSENKSSA-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
Phoma herbarum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Coumaric acid ester
Cinnamic acid ester
Coumaric acid or derivatives
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary carboxylic acid amide
Ketone
Carboxylic acid ester
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.41	ChemAxon
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.43 m³·mol⁻¹	ChemAxon
Polarizability	29.87 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

78435256

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132608798

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate (NP0289742)

MOL for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

3D MOL for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

3D SDF for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

3D-SDF for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

PDB for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

3D PDB for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

SMILES for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

INCHI for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

Structure for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)

3D Structure for NP0289742 (methyl (2z)-3-(4-hydroxyphenyl)-2-(3-methyl-2-oxobutanamido)prop-2-enoate)