NP-MRD: Showing NP-Card for 2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol (NP0227659)

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Record Information

Version

2.0

Created at

2022-09-06 07:03:21 UTC

Updated at

2022-09-06 07:03:21 UTC

NP-MRD ID

NP0227659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol

Description

Gelliusine A belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. 2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol was first documented in 1994 (PMID: 7798965). Based on a literature review very few articles have been published on Gelliusine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209032D          

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M  END

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 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
 12 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 26 35  1  0  0  0  0
 29 35  1  0  0  0  0
 22 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
  4 39  1  0  0  0  0
 20 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC1=C(NC2=CC(C(CN)C3=CNC4=CC(Br)=CC=C34)=C(O)C=C12)C(CN)C1=CNC2=CC(Br)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C30H30Br2N6O/c31-15-1-3-17-24(13-36-26(17)7-15)22(11-34)21-9-28-20(10-29(21)39)19(5-6-33)30(38-28)23(12-35)25-14-37-27-8-16(32)2-4-18(25)27/h1-4,7-10,13-14,22-23,36-39H,5-6,11-12,33-35H2

> <INCHI_KEY>
CYAJKOUHPRYFRD-UHFFFAOYSA-N

> <FORMULA>
C30H30Br2N6O

> <MOLECULAR_WEIGHT>
650.419

> <EXACT_MASS>
648.084786

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
64.29694063340104

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-bis[2-amino-1-(6-bromo-1H-indol-3-yl)ethyl]-3-(2-aminoethyl)-1H-indol-5-ol

> <JCHEM_LOGP>
3.310117095796658

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA>
15.92480709789734

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.744523217141263

> <JCHEM_PKA_STRONGEST_BASIC>
10.164218068701585

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
165.29510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,6-bis[2-amino-1-(6-bromo-1H-indol-3-yl)ethyl]-3-(2-aminoethyl)-1H-indol-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  N   UNK     0       7.551 -10.660   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.026  -9.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.996  -8.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.472  -6.586   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.567  -5.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.027  -5.340   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.257  -4.007   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.717  -4.007   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.257  -6.674   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.883  -8.081   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.739  -9.111   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.405  -8.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.940  -8.817   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.204  -7.787   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0      -1.669  -8.263   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       0.116  -6.280   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.581  -5.805   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.725  -6.835   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.472  -4.094   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       8.937  -4.570   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.270  -3.800   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.604  -4.570   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.938  -3.800   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.271  -4.570   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      15.605  -3.800   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      12.938  -2.260   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.692  -1.355   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      12.168   0.109   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      13.708   0.109   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.738   1.254   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.244   0.934   0.000  0.00  0.00           C+0
HETATM   32 Br   UNK     0      17.275   2.078   0.000  0.00  0.00          Br+0
HETATM   33  C   UNK     0      16.720  -0.531   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.690  -1.675   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.183  -1.355   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.604  -6.110   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.938  -6.880   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.270  -6.880   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.937  -6.110   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   39                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    9   12                                                  
CONECT   19    5   20                                                       
CONECT   20   19   21   39                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   36                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   26   29                                                  
CONECT   36   22   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38    4   20                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
Gelliusine b	MeSH

Chemical Formula

C₃₀H₃₀Br₂N₆O

Average Mass

650.4190 Da

Monoisotopic Mass

648.08479 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

NCCC1=C(NC2=CC(C(CN)C3=CNC4=CC(Br)=CC=C34)=C(O)C=C12)C(CN)C1=CNC2=CC(Br)=CC=C12

InChI Identifier

InChI=1S/C30H30Br2N6O/c31-15-1-3-17-24(13-36-26(17)7-15)22(11-34)21-9-28-20(10-29(21)39)19(5-6-33)30(38-28)23(12-35)25-14-37-27-8-16(32)2-4-18(25)27/h1-4,7-10,13-14,22-23,36-39H,5-6,11-12,33-35H2

InChI Key

CYAJKOUHPRYFRD-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Hydroxyindole
3-alkylindole
Indole
2-arylethylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Aryl bromide
Aryl halide
Benzenoid
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Azacycle
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Primary aliphatic amine
Organopnictogen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039255

Chemspider ID

138872

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157833

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bifulco G, Bruno I, Minale L, Riccio R, Calignano A, Debitus C: (+/-)-Gelliusines A and B, two diastereomeric brominated tris-indole alkaloids from a deep water new caledonian marine sponge (Gellius or Orina sp.). J Nat Prod. 1994 Sep;57(9):1294-9. doi: 10.1021/np50111a020. [PubMed:7798965 ]
LOTUS database [Link]

Showing NP-Card for 2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol (NP0227659)

MOL for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

3D MOL for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

3D SDF for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

3D-SDF for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

PDB for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

3D PDB for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

SMILES for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

INCHI for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

Structure for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)

3D Structure for NP0227659 (2,6-bis[2-amino-1-(6-bromo-1h-indol-3-yl)ethyl]-3-(2-aminoethyl)-1h-indol-5-ol)