NP-MRD: Showing NP-Card for 3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol (NP0229352)

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Record Information

Version

2.0

Created at

2022-09-06 09:22:18 UTC

Updated at

2022-09-06 09:22:18 UTC

NP-MRD ID

NP0229352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol

Description

3-{[7-(3-Chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Based on a literature review very few articles have been published on 3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062211222D          

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M  END

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  Mrv1652309062211222D          

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  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  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 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
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  2  0  0  0  0
 26 27  1  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
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1N=C(O)C(CC2=C(NC3=C(CC(O)C(C)(C)Cl)C=C(CC=C(C)C)C=C23)C(C)(C)C=C)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40ClN3O3/c1-9-28(5,6)25-21(15-22-27(36)31-17(4)26(35)32-22)20-13-18(11-10-16(2)3)12-19(24(20)33-25)14-23(34)29(7,8)30/h9-10,12-13,17,22-23,33-34H,1,11,14-15H2,2-8H3,(H,31,36)(H,32,35)

> <INCHI_KEY>
KORJXHWEJZNGQF-UHFFFAOYSA-N

> <FORMULA>
C29H40ClN3O3

> <MOLECULAR_WEIGHT>
514.11

> <EXACT_MASS>
513.2758199

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.31074343869264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol

> <JCHEM_LOGP>
3.9370593988176146

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.688199156151403

> <JCHEM_PKA_STRONGEST_ACIDIC>
-8.505435892195035

> <JCHEM_PKA_STRONGEST_BASIC>
14.828679023824025

> <JCHEM_POLAR_SURFACE_AREA>
101.2

> <JCHEM_REFRACTIVITY>
148.4164

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol

> <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  C   UNK     0      -1.653  -3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -2.843   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   0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.860  -1.303   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       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.591   1.777   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.258   4.087   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258   5.627   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.718   4.087   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       7.798   4.087   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.259   0.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       4.187  -4.838   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       5.217  -5.982   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.723  -5.662   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.741  -7.447   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.772  -8.591   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       3.235  -7.767   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.698  -6.943   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   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    9   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25                                                       
CONECT   25   24    8   26                                                  
CONECT   26   25    6   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   28   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀ClN₃O₃

Average Mass

514.1100 Da

Monoisotopic Mass

513.27582 Da

IUPAC Name

3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol

Traditional Name

3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol

CAS Registry Number

Not Available

SMILES

CC1N=C(O)C(CC2=C(NC3=C(CC(O)C(C)(C)Cl)C=C(CC=C(C)C)C=C23)C(C)(C)C=C)N=C1O

InChI Identifier

InChI=1S/C29H40ClN3O3/c1-9-28(5,6)25-21(15-22-27(36)31-17(4)26(35)32-22)20-13-18(11-10-16(2)3)12-19(24(20)33-25)14-23(34)29(7,8)30/h9-10,12-13,17,22-23,33-34H,1,11,14-15H2,2-8H3,(H,31,36)(H,32,35)

InChI Key

KORJXHWEJZNGQF-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 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Cyclic carboximidic acid
Chlorohydrin
Halohydrin
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Alkyl chloride
Alkyl halide
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	3.94	ChemAxon
pKa (Strongest Acidic)	-8.5	ChemAxon
pKa (Strongest Basic)	14.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	101.2 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	148.42 m³·mol⁻¹	ChemAxon
Polarizability	57.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

142737380

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol (NP0229352)

MOL for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

3D MOL for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

3D SDF for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

3D-SDF for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

PDB for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

3D PDB for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

SMILES for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

INCHI for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

Structure for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)

3D Structure for NP0229352 (3-{[7-(3-chloro-2-hydroxy-3-methylbutyl)-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol)