NP-MRD: Showing NP-Card for dimethylallyltryptophan (NP0184859)

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Record Information

Version

1.0

Created at

2022-09-04 00:05:44 UTC

Updated at

2022-09-04 00:05:44 UTC

NP-MRD ID

NP0184859

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dimethylallyltryptophan

Description

Tryptophan, 4-(3-methyl-2-butenyl)-, also known as 4-dimethylallyltryptophan, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Tryptophan, 4-(3-methyl-2-butenyl)- is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    1.3541    1.4441    2.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986    1.1202    1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    2.2427    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035   -0.0376    0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -1.2349    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033   -2.0229   -0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -3.1751   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6620   -4.0267   -1.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5864   -3.7804   -1.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644   -2.6661   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4818   -2.2174   -1.7582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527   -1.1265   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396   -0.7977   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    0.4438    0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615    1.6559   -0.4314 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2085    1.6594   -1.2188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042    2.8686    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    2.9763    1.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5808    3.8716    0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -1.7868   -0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659    0.6377    2.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    1.7352    3.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015    2.3604    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726    3.1906    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775    2.0604   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437    2.3507    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -0.1253   -0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185   -1.8317    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664   -0.9573    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -3.3306   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213   -4.8914   -1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588   -4.4375   -2.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -2.6841   -2.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863   -0.5820   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0825    0.5198    1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    0.6360    0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663    1.7138   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736    2.5965   -1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360    1.2156   -2.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695    4.4126    1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6 20  2  0
 20 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 19  1  0
 17 18  2  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
 10 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  6
 16 38  1  0
 16 39  1  0
 19 40  1  0
 12 34  1  0
 11 33  1  0
  9 32  1  0
  8 31  1  0
  7 30  1  0
M  END


  Mrv1533004161521272D          

 20 21  0  0  0  0            999 V2000
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659    1.4230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    2.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    3.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  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  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  0  0  0  0
  5 19  2  0  0  0  0
  9 19  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2C(CC(N)C(O)=O)=CNC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O2/c1-10(2)6-7-11-4-3-5-14-15(11)12(9-18-14)8-13(17)16(19)20/h3-6,9,13,18H,7-8,17H2,1-2H3,(H,19,20)

> <INCHI_KEY>
MZSPRSJAOSKAAT-UHFFFAOYSA-N

> <FORMULA>
C16H20N2O2

> <MOLECULAR_WEIGHT>
272.348

> <EXACT_MASS>
272.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.15206107114836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-3-[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
0.6427537780566767

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.08726295075115

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3267336137816264

> <JCHEM_PKA_STRONGEST_BASIC>
9.392358121471124

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
80.44559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylallyltryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.340   3.801   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.310   2.656   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.864   5.265   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.642   5.586   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.895   6.410   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12    5    9                                                  
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
4-Dimethylallyltryptophan	Kegg

Chemical Formula

C₁₆H₂₀N₂O₂

Average Mass

272.3480 Da

Monoisotopic Mass

272.15248 Da

IUPAC Name

2-amino-3-[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

Traditional Name

dimethylallyltryptophan

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2C(CC(N)C(O)=O)=CNC2=CC=C1

InChI Identifier

InChI=1S/C16H20N2O2/c1-10(2)6-7-11-4-3-5-14-15(11)12(9-18-14)8-13(17)16(19)20/h3-6,9,13,18H,7-8,17H2,1-2H3,(H,19,20)

InChI Key

MZSPRSJAOSKAAT-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 indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:28473 )
tryptophan derivative (CHEBI:28473 )

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	0.16	ALOGPS
logP	0.64	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	2.33	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.45 m³·mol⁻¹	ChemAxon
Polarizability	30.15 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

C06067

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440903

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for dimethylallyltryptophan (NP0184859)

MOL for NP0184859 (dimethylallyltryptophan)

3D MOL for NP0184859 (dimethylallyltryptophan)

3D SDF for NP0184859 (dimethylallyltryptophan)

3D-SDF for NP0184859 (dimethylallyltryptophan)

PDB for NP0184859 (dimethylallyltryptophan)

3D PDB for NP0184859 (dimethylallyltryptophan)

SMILES for NP0184859 (dimethylallyltryptophan)

INCHI for NP0184859 (dimethylallyltryptophan)

Structure for NP0184859 (dimethylallyltryptophan)

3D Structure for NP0184859 (dimethylallyltryptophan)