NP-MRD: Showing NP-Card for ({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine (NP0257673)

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Record Information

Version

2.0

Created at

2022-09-07 22:51:47 UTC

Updated at

2022-09-07 22:51:48 UTC

NP-MRD ID

NP0257673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine

Description

({5'-Bromo-4-methoxy-1'H,5H-[2,2'-bipyrrole]-5-ylidene}methyl)(butan-2-yl)amine belongs to the class of organic compounds known as aryl bromides. ({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine is found in Virididentula dentata. These are organic compounds containing the acyl bromide functional group ({5'-bromo-4-methoxy-1'H,5H-[2,2'-bipyrrole]-5-ylidene}methyl)(butan-2-yl)amine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.9293   -1.5285    1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6870   -1.0388    1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.4829   -0.2537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7160   -1.5433   -1.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8996    0.0862   -0.9038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    1.1611   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346    1.0236   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9392   -0.0966   -0.5409 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567    0.1754   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -0.7392   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -2.0034   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5317   -2.5369   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3408   -1.5620   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2313   -1.7689   -0.2792 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5835   -0.5032   -0.1488 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    1.5031    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0260    2.0437    0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6793    3.3025    0.8737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3868    4.3985    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462   -2.3599    2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3681   -0.6665    2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543   -1.9280    1.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2363   -0.2640    1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348   -1.8419    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900    0.3465   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8222   -1.4593   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969   -2.5672   -0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4101   -1.4178   -2.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6174   -0.3301   -1.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6707    2.0473   -0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3620   -2.5224   -1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8570   -3.5129   -1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    0.3775    0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    2.0036    0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478    5.2568    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851    4.2274   -0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2660    4.7203   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 17  7  1  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  1
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
M  END


  Mrv1533004231523132D          

 19 20  0  0  0  0            999 V2000
   -0.1725    2.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    1.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564    1.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    0.2323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672   -0.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -2.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788   -2.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -3.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663   -4.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663   -5.0367    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -3.7268    0.0000 N   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
  3  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  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
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  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
 17 19  1  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)NC=C1N=C(C=C1OC)C1=CC=C(Br)N1

> <INCHI_IDENTIFIER>
InChI=1S/C14H18BrN3O/c1-4-9(2)16-8-12-13(19-3)7-11(17-12)10-5-6-14(15)18-10/h5-9,16,18H,4H2,1-3H3

> <INCHI_KEY>
BZLJCPZSIUDROQ-UHFFFAOYSA-N

> <FORMULA>
C14H18BrN3O

> <MOLECULAR_WEIGHT>
324.222

> <EXACT_MASS>
323.063325

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.47850512860075

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[5-(5-bromo-1H-pyrrol-2-yl)-3-methoxy-2H-pyrrol-2-ylidene]methyl}(butan-2-yl)amine

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
1.780036880333333

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.199982387156155

> <JCHEM_PKA_STRONGEST_BASIC>
7.231829998990214

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
82.79770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[5-(5-bromo-1H-pyrrol-2-yl)-3-methoxypyrrol-2-ylidene]methyl}(sec-butyl)amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -0.322   4.284   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.322   2.744   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.012   1.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.345   2.744   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.012   0.434   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.591  -2.782   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.115  -4.246   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.099  -2.782   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.365  -2.306   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.685  -0.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.021  -5.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.561  -5.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.036  -6.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.791  -7.862   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0       4.791  -9.402   0.000  0.00  0.00          Br+0
HETATM   19  N   UNK     0       3.545  -6.957   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈BrN₃O

Average Mass

324.2220 Da

Monoisotopic Mass

323.06332 Da

IUPAC Name

{[5-(5-bromo-1H-pyrrol-2-yl)-3-methoxy-2H-pyrrol-2-ylidene]methyl}(butan-2-yl)amine

Traditional Name

{[5-(5-bromo-1H-pyrrol-2-yl)-3-methoxypyrrol-2-ylidene]methyl}(sec-butyl)amine

CAS Registry Number

Not Available

SMILES

CCC(C)NC=C1N=C(C=C1OC)C1=CC=C(Br)N1

InChI Identifier

InChI=1S/C14H18BrN3O/c1-4-9(2)16-8-12-13(19-3)7-11(17-12)10-5-6-14(15)18-10/h5-9,16,18H,4H2,1-3H3

InChI Key

BZLJCPZSIUDROQ-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
Virididentula dentata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl bromides. These are organic compounds containing the acyl bromide functional group.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Aryl halides

Sub Class

Aryl bromides

Direct Parent

Aryl bromides

Alternative Parents

Substituents

Aryl bromide
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Ketimine
Secondary aliphatic amine
Enamine
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organobromide
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Imine
Organic oxygen compound
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	3.48	ALOGPS
logP	1.78	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.2	ChemAxon
pKa (Strongest Basic)	7.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.8 m³·mol⁻¹	ChemAxon
Polarizability	32.48 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine (NP0257673)

MOL for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

3D MOL for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

3D SDF for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

3D-SDF for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

PDB for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

3D PDB for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

SMILES for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

INCHI for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

Structure for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)

3D Structure for NP0257673 (({5'-bromo-4-methoxy-1'h-[2,2'-bipyrrol]-5-ylidene}methyl)(sec-butyl)amine)