NP-MRD: Showing NP-Card for (2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate (NP0244627)

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Record Information

Version

2.0

Created at

2022-09-07 05:28:38 UTC

Updated at

2022-09-07 05:28:39 UTC

NP-MRD ID

NP0244627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate

Description

6-Bromohypaphorine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. (2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate was first documented in 2015 (PMID: 26008231). Based on a literature review a small amount of articles have been published on 6-Bromohypaphorine (PMID: 35538277) (PMID: 30413031) (PMID: 25775422).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -2.3501    1.1889    1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318    0.5113    0.0964 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1696   -0.7208    0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2097    1.3182   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1035    0.2681   -0.3779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4466   -0.9071    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -1.1673   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225   -2.1424   -1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7482   -2.0010   -1.1821 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202   -0.9400   -0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3889   -0.3866   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5401    0.7200    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2832    1.4619    0.7116 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4457    1.2713    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    0.7159    0.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.3950    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722    0.1248   -1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    1.1853   -2.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862   -1.0406   -2.5412 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.3677    1.4616    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9515    0.4810    2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    2.0480    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686   -1.1049    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -1.4718   -0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2494   -0.4708    0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7742    2.3214   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2227    1.4365   -0.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    0.7565   -1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    1.1720   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855   -0.7705    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330   -1.8442    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980   -2.9163   -1.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.6187   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582   -0.8151   -0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094    2.1377    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3553    1.1325    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
  5 17  1  0
 17 19  1  0
 17 18  2  0
 16  7  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 14 35  1  0
 15 36  1  0
M  CHG  2   2   1  19  -1
M  END


  Mrv1652309072207282D          

 19 20  0  0  1  0            999 V2000
   -0.4331   -3.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.6065   -3.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628   -2.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  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
    1.1387   -1.3654    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
    4.0668    0.1271    0.0000 Br  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
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  6  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  7 16  1  0  0  0  0
 10 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  CHG  2   2   1  19  -1
M  END
> <DATABASE_ID>
NP0244627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)[C@@H](CC1=CNC2=CC(Br)=CC=C12)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17BrN2O2/c1-17(2,3)13(14(18)19)6-9-8-16-12-7-10(15)4-5-11(9)12/h4-5,7-8,13,16H,6H2,1-3H3/t13-/m0/s1

> <INCHI_KEY>
WWGWMAVAOTWHTF-ZDUSSCGKSA-N

> <FORMULA>
C14H17BrN2O2

> <MOLECULAR_WEIGHT>
325.206

> <EXACT_MASS>
324.047341

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.30369997323449

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(6-bromo-1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate

> <JCHEM_LOGP>
-1.4015786141384123

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.819933219015486

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7739499215566679

> <JCHEM_POLAR_SURFACE_AREA>
55.92

> <JCHEM_REFRACTIVITY>
100.6456

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-(6-bromo-1H-indol-3-yl)-2-(trimethylammonio)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.808  -7.263   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       1.132  -6.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.797  -5.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       7.591   0.237   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   10                                                  
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
D-6-Bromohypaphorine	MeSH
L-6-Bromohypaporphine	MeSH

Chemical Formula

C₁₄H₁₇BrN₂O₂

Average Mass

325.2060 Da

Monoisotopic Mass

324.04734 Da

IUPAC Name

(2S)-3-(6-bromo-1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate

Traditional Name

(2S)-3-(6-bromo-1H-indol-3-yl)-2-(trimethylammonio)propanoate

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)[C@@H](CC1=CNC2=CC(Br)=CC=C12)C([O-])=O

InChI Identifier

InChI=1S/C14H17BrN2O2/c1-17(2,3)13(14(18)19)6-9-8-16-12-7-10(15)4-5-11(9)12/h4-5,7-8,13,16H,6H2,1-3H3/t13-/m0/s1

InChI Key

WWGWMAVAOTWHTF-ZDUSSCGKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

3-alkylindole
L-alpha-amino acid
Indole
Indole or derivatives
Aralkylamine
Aryl bromide
Aryl halide
Substituted pyrrole
Benzenoid
Pyrrole
Quaternary ammonium salt
Tetraalkylammonium salt
Heteroaromatic compound
Carboxylic acid salt
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organobromide
Organohalogen compound
Organooxygen compound
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Organic oxygen compound
Organic salt
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	-1.4	ChemAxon
pKa (Strongest Acidic)	1.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.65 m³·mol⁻¹	ChemAxon
Polarizability	30.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

111378

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

125123

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shaykhutdinova ER, Kondrakhina AE, Ivanov IA, Kudryavtsev DS, Dyachenko IA, Murashev AN, Tsetlin VI, Utkin YN: Synthetic Analogs of 6-Bromohypaphorine, a Natural Agonist of Nicotinic Acetylcholine Receptors, Reduce Cardiac Reperfusion Injury in a Rat Model of Myocardial Ischemia. Dokl Biochem Biophys. 2022 Apr;503(1):47-51. doi: 10.1134/S1607672922020132. Epub 2022 May 10. [PubMed:35538277 ]
Di X, Rouger C, Hardardottir I, Freysdottir J, Molinski TF, Tasdemir D, Omarsdottir S: 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity. Mar Drugs. 2018 Nov 8;16(11):437. doi: 10.3390/md16110437. [PubMed:30413031 ]
Kudryavtsev D, Shelukhina I, Vulfius C, Makarieva T, Stonik V, Zhmak M, Ivanov I, Kasheverov I, Utkin Y, Tsetlin V: Natural compounds interacting with nicotinic acetylcholine receptors: from low-molecular weight ones to peptides and proteins. Toxins (Basel). 2015 May 14;7(5):1683-701. doi: 10.3390/toxins7051683. [PubMed:26008231 ]
Kasheverov IE, Shelukhina IV, Kudryavtsev DS, Makarieva TN, Spirova EN, Guzii AG, Stonik VA, Tsetlin VI: 6-bromohypaphorine from marine nudibranch mollusk Hermissenda crassicornis is an agonist of human alpha7 nicotinic acetylcholine receptor. Mar Drugs. 2015 Mar 12;13(3):1255-66. doi: 10.3390/md13031255. [PubMed:25775422 ]
LOTUS database [Link]

Showing NP-Card for (2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate (NP0244627)

MOL for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

3D MOL for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

3D SDF for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

3D-SDF for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

PDB for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

3D PDB for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

SMILES for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

INCHI for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

Structure for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)

3D Structure for NP0244627 ((2s)-3-(6-bromo-1h-indol-3-yl)-2-(trimethylammonio)propanoate)