NP-MRD: Showing NP-Card for (2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid (NP0324583)

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Record Information

Version

2.0

Created at

2022-09-12 04:44:59 UTC

Updated at

2022-09-12 04:44:59 UTC

NP-MRD ID

NP0324583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid

Description

7-(3-Methylbut-2-enyl)-L-tryptophan, also known as 7-prenyl-L-tryptophan, 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. (2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid is found in Apis cerana and Aspergillus fumigatus. Based on a literature review very few articles have been published on 7-(3-methylbut-2-enyl)-L-tryptophan.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.6570   -1.0277    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4057   -0.3652   -0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0788   -0.2436   -1.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682    0.0893    0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    0.7483    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918   -0.0274    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0990   -1.4056    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -2.0743    0.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -1.4037    0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3080   -0.0271    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306    0.8885    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    0.5583    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5161    0.5037   -0.0538 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5203    1.8096   -0.7433 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0721   -0.5195   -1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7373   -0.1650   -2.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0396   -1.8367   -0.6576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322    2.1149    0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234    1.9584    0.7018 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1044    0.6287    0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5373   -0.5318   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5853   -2.1080   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7536   -1.0397    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0630   -0.7286   -1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9537    0.7757   -2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8369   -0.7386   -2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7894   -0.0192    1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3146    0.9637   -0.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2636    1.7707    0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443   -1.8972    0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041   -3.1676    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865   -1.9101    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7983   -0.4855    1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2944    1.1814    1.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775    0.2807    0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4009    2.5915   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8637    1.7775   -1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3685   -2.6246   -1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    3.0377    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    2.6686    0.5543 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 19  1  0
 19 18  1  0
 18 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 17  1  0
 15 16  2  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
 19 40  1  0
 18 39  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  1
 14 36  1  0
 14 37  1  0
 17 38  1  0
  9 32  1  0
  8 31  1  0
  7 30  1  0
M  END


  Mrv1652309122206452D          

 20 21  0  0  1  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
    4.7079    1.2375    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -1.6527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8839   -1.4811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -3.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150   -2.6088    0.0000 O   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 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  2  0  0  0  0
 10 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324583

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2NC=C(C[C@H](N)C(O)=O)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O2/c1-10(2)6-7-11-4-3-5-13-12(9-18-15(11)13)8-14(17)16(19)20/h3-6,9,14,18H,7-8,17H2,1-2H3,(H,19,20)/t14-/m0/s1

> <INCHI_KEY>
OLFAGKNOXHVNHG-AWEZNQCLSA-N

> <FORMULA>
C16H20N2O2

> <MOLECULAR_WEIGHT>
272.348

> <EXACT_MASS>
272.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.7747964760107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

> <JCHEM_LOGP>
0.6429834900026621

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.945772094019993

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4786068150899445

> <JCHEM_PKA_STRONGEST_BASIC>
9.395369585547364

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
80.4456

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         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       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.877  -3.085   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.383  -2.765   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.401  -4.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.432  -5.694   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.895  -4.870   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
7-Prenyl-L-tryptophan	Kegg

Chemical Formula

C₁₆H₂₀N₂O₂

Average Mass

272.3480 Da

Monoisotopic Mass

272.15248 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2NC=C(C[C@H](N)C(O)=O)C2=CC=C1

InChI Identifier

InChI=1S/C16H20N2O2/c1-10(2)6-7-11-4-3-5-13-12(9-18-15(11)13)8-14(17)16(19)20/h3-6,9,14,18H,7-8,17H2,1-2H3,(H,19,20)/t14-/m0/s1

InChI Key

OLFAGKNOXHVNHG-AWEZNQCLSA-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
Apis cerana	LOTUS Database	35616633
Aspergillus fumigatus	LOTUS Database	35616633

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
L-alpha-amino acid
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 L-alpha-amino acid (CHEBI:59356 )
L-tryptophan derivative (CHEBI:59356 )

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

Not Available

Chemspider ID

26331579

KEGG Compound ID

C19767

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45479458

PDB ID

Not Available

ChEBI ID

59356

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid (NP0324583)

MOL for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

3D MOL for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

3D SDF for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

3D-SDF for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

PDB for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

3D PDB for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

SMILES for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

INCHI for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

Structure for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)

3D Structure for NP0324583 ((2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid)