NP-MRD: Showing NP-Card for n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid (NP0203709)

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Record Information

Version

2.0

Created at

2022-09-04 23:13:57 UTC

Updated at

2022-09-04 23:13:57 UTC

NP-MRD ID

NP0203709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid

Description

Brocaeloid B belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid is found in Penicillium brocae. Based on a literature review very few articles have been published on Brocaeloid B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 44  0  0  0  0  0  0  0  0999 V2000
   -3.5992    2.7660    1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1361    1.5802    1.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5303    1.0022    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    0.6626    0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983    2.0581   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6602   -0.1481   -0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622   -0.6983   -1.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7635   -0.6164    0.6425 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -1.7006    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -2.9568    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6879   -4.0412   -0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6418   -3.8699   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911   -2.5837   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036   -1.4786    0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -0.1392    0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023    0.7610    0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915    0.4751   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994   -0.2921   -0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5049    0.6948   -0.5904 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3551    0.8750    0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4174    1.8916    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3721    0.2217    1.5553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2619    3.3640    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3099    3.1776    2.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4847    1.0336    2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1600   -0.1888   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5456    1.5516   -0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104    0.3600    1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2247    2.3183   -0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    2.9564   -0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6103    1.5889   -1.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9728   -1.6893   -1.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335   -3.1153    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1218   -5.0391   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -4.7290   -0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2326   -2.4817   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476    1.3169   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332    1.0333    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458   -0.7544   -1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -1.0215    0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3490    1.6822    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0519    2.9171    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6686    1.8948   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9031   -0.6391    1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  1  0
 20 19  2  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  3  1  0
  3  4  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  9 14  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 18 39  1  0
 18 40  1  0
 17 37  1  0
 17 38  1  0
 13 36  1  0
 12 35  1  0
 11 34  1  0
 10 33  1  0
  7 32  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  2 25  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652309052201132D          

 22 22  0  0  0  0            999 V2000
    2.1434    4.5375    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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    0.0000 C   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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   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
    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
    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 N   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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  2  0  0  0  0
 10 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
  9 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  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NCCC(=O)C1=CC=CC=C1N=C(O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O3/c1-5-17(3,4)16(22)19-14-9-7-6-8-13(14)15(21)10-11-18-12(2)20/h5-9H,1,10-11H2,2-4H3,(H,18,20)(H,19,22)

> <INCHI_KEY>
FROOGKVRWMYTPK-UHFFFAOYSA-N

> <FORMULA>
C17H22N2O3

> <MOLECULAR_WEIGHT>
302.374

> <EXACT_MASS>
302.163042576

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.715301642990525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid

> <JCHEM_LOGP>
2.5261672810506104

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.971922735756555

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9021606066226115

> <JCHEM_PKA_STRONGEST_BASIC>
6.139850970739934

> <JCHEM_POLAR_SURFACE_AREA>
82.25

> <JCHEM_REFRACTIVITY>
88.451

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid

> <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       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.127   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -5.335   1.540   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂N₂O₃

Average Mass

302.3740 Da

Monoisotopic Mass

302.16304 Da

IUPAC Name

N-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid

Traditional Name

N-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NCCC(=O)C1=CC=CC=C1N=C(O)C(C)(C)C=C

InChI Identifier

InChI=1S/C17H22N2O3/c1-5-17(3,4)16(22)19-14-9-7-6-8-13(14)15(21)10-11-18-12(2)20/h5-9H,1,10-11H2,2-4H3,(H,18,20)(H,19,22)

InChI Key

FROOGKVRWMYTPK-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
Penicillium brocae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Anilide
Benzoyl
N-arylamide
Aryl alkyl ketone
Monocyclic benzene moiety
Benzenoid
Vinylogous amide
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organic nitrogen compound
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	2.53	ChemAxon
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	6.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.25 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	88.45 m³·mol⁻¹	ChemAxon
Polarizability	32.72 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

34981948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101906483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid (NP0203709)

MOL for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

3D MOL for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

3D SDF for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

3D-SDF for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

PDB for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

3D PDB for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

SMILES for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

INCHI for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

Structure for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)

3D Structure for NP0203709 (n-(2-{3-[(1-hydroxyethylidene)amino]propanoyl}phenyl)-2,2-dimethylbut-3-enimidic acid)