NP-MRD: Showing NP-Card for n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid (NP0329973)

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Record Information

Version

2.0

Created at

2022-09-12 14:53:04 UTC

Updated at

2022-09-12 14:53:04 UTC

NP-MRD ID

NP0329973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid

Description

Brocaeloid C belongs to the class of organic compounds known as n-acetyl-2-arylethylamines. N-acetyl-2-arylethylamines are compounds containing an acetamide group that is N-linked to an arylethylamine. n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid is found in Penicillium brocae. Based on a literature review very few articles have been published on Brocaeloid C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -1.7460   -3.2075   -1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308   -2.5169   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9548   -1.3573    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2455   -1.0504   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275   -1.7666    1.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1372   -0.1358    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    0.4883    1.8592 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1363    1.5926    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3972    2.5688    2.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336    3.6322    2.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624    3.7518    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    2.7903   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068    1.7371    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296    0.6398   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671    0.3999   -1.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675   -0.5131   -2.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    0.1577   -1.7017 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9100   -0.4708   -1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061    0.3081   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8777   -1.8328   -1.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340   -3.0063   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578   -4.0535   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3842   -2.8686    0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -1.1399   -1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0960   -1.6596    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480    0.0445    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1796   -2.5899    1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580   -2.1419    2.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8780   -0.9029    2.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1859    0.1582    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250    2.4849    3.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477    4.3919    2.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9408    4.5904    0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0049    2.8622   -1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215    1.3764   -2.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.1037   -2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -0.6316   -3.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -1.5001   -1.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195   -0.3157   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2496    1.1270   -1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8721    0.8494    0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6293   -2.3939   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  3  1  0
  3  4  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
 13 14  1  0
 13  8  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  0
 15 36  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  2 23  1  0
  1 21  1  0
  1 22  1  0
M  END


  Mrv1652309122216532D          

 20 21  0  0  0  0            999 V2000
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NCCC1=C(NC2=CC=CC=C12)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O/c1-5-17(3,4)16-14(10-11-18-12(2)20)13-8-6-7-9-15(13)19-16/h5-9,19H,1,10-11H2,2-4H3,(H,18,20)

> <INCHI_KEY>
QNYYNQFTMLZVMA-UHFFFAOYSA-N

> <FORMULA>
C17H22N2O

> <MOLECULAR_WEIGHT>
270.376

> <EXACT_MASS>
270.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.61268128130935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl}ethanimidic acid

> <JCHEM_LOGP>
3.1892243048479583

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.506259542625731

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.013026311534564

> <JCHEM_PKA_STRONGEST_BASIC>
7.075962030336576

> <JCHEM_POLAR_SURFACE_AREA>
48.379999999999995

> <JCHEM_REFRACTIVITY>
83.52690000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-{2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl}ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.320   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.869  -4.974   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   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂N₂O

Average Mass

270.3760 Da

Monoisotopic Mass

270.17321 Da

IUPAC Name

N-{2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl}ethanimidic acid

Traditional Name

N-{2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl}ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NCCC1=C(NC2=CC=CC=C12)C(C)(C)C=C

InChI Identifier

InChI=1S/C17H22N2O/c1-5-17(3,4)16-14(10-11-18-12(2)20)13-8-6-7-9-15(13)19-16/h5-9,19H,1,10-11H2,2-4H3,(H,18,20)

InChI Key

QNYYNQFTMLZVMA-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 n-acetyl-2-arylethylamines. N-acetyl-2-arylethylamines are compounds containing an acetamide group that is N-linked to an arylethylamine.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

N-acetyl-2-arylethylamines

Alternative Parents

Substituents

N-acetyl-2-arylethylamine
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.19	ChemAxon
pKa (Strongest Acidic)	5.01	ChemAxon
pKa (Strongest Basic)	7.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.53 m³·mol⁻¹	ChemAxon
Polarizability	31.61 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

34981946

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101906484

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-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid (NP0329973)

MOL for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

3D MOL for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

3D SDF for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

3D-SDF for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

PDB for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

3D PDB for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

SMILES for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

INCHI for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

Structure for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)

3D Structure for NP0329973 (n-{2-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]ethyl}ethanimidic acid)