NP-MRD: Showing NP-Card for Tuftsin (NP0087409)

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Record Information

Version

2.0

Created at

2022-05-11 16:48:54 UTC

Updated at

2022-05-11 16:48:54 UTC

NP-MRD ID

NP0087409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tuftsin

Description

Tuftsin, also known as taftsin, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Tuftsin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220282D          

 35 35  0  0  1  0            999 V2000
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   14.4738   -9.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02231220282D          

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M  END
> <DATABASE_ID>
NP0087409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](N)C(=O)NC(CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H40N8O6/c1-12(30)16(23)18(32)27-13(6-2-3-9-22)19(33)29-11-5-8-15(29)17(31)28-14(20(34)35)7-4-10-26-21(24)25/h12-16,30H,2-11,22-23H2,1H3,(H,27,32)(H,28,31)(H,34,35)(H4,24,25,26)/t12-,13?,14+,15+,16+/m1/s1

> <INCHI_KEY>
IESDGNYHXIOKRW-NNFXCFJSSA-N

> <FORMULA>
C21H40N8O6

> <MOLECULAR_WEIGHT>
500.5923

> <EXACT_MASS>
500.307081052

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
52.580176108647834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-1-{6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanoyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

> <ALOGPS_LOGP>
-3.31

> <JCHEM_LOGP>
-5.348810549141742

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.56689568703618

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4362361526004426

> <JCHEM_PKA_STRONGEST_BASIC>
11.8990047822635

> <JCHEM_POLAR_SURFACE_AREA>
249.97999999999996

> <JCHEM_REFRACTIVITY>
136.77910000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-1-{6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanoyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      16.480 -17.569   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.243 -23.069   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.082 -24.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.857 -15.894   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.860 -16.316   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.650 -22.443   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.018 -17.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.392 -16.477   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.675 -25.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.103 -14.989   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.234 -17.723   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.073 -18.195   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.811 -20.911   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.772 -18.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.712 -17.983   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.912 -19.727   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.119 -18.609   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.158 -20.632   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.217 -20.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.933 -19.862   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.188 -12.552   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      15.514 -26.758   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      13.505 -20.353   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      30.594 -13.178   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      29.027 -11.020   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      27.942 -13.457   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      17.565 -20.006   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      24.365 -17.704   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      20.379 -18.753   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0      13.827 -17.290   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      23.280 -20.141   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      15.997 -22.164   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      21.463 -21.190   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      24.687 -20.767   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      27.340 -20.489   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    6    3                                                       
CONECT    3    2    9                                                       
CONECT    4    7   10                                                       
CONECT    5   11    8                                                       
CONECT    6    2   13                                                       
CONECT    7    4   14                                                       
CONECT    8    5   15                                                       
CONECT    9    3   22                                                       
CONECT   10    4   26                                                       
CONECT   11    5   29                                                       
CONECT   12    1   30   16                                                  
CONECT   13    6   27   19                                                  
CONECT   14    7   28   20                                                  
CONECT   15    8   29   17                                                  
CONECT   16   12   23   18                                                  
CONECT   17   15   31   28                                                  
CONECT   18   16   32   27                                                  
CONECT   19   13   33   29                                                  
CONECT   20   14   34   35                                                  
CONECT   21   26   24   25                                                  
CONECT   22    9                                                            
CONECT   23   16                                                            
CONECT   24   21                                                            
CONECT   25   21                                                            
CONECT   26   10   21                                                       
CONECT   27   13   18                                                       
CONECT   28   14   17                                                       
CONECT   29   11   15   19                                                  
CONECT   30   12                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   20                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Value	Source
L-Threonyl-L-lysyl-L-prolyl-L-arginine	HMDB
Taftsin	HMDB
L-THR-L-Lys-L-pro-L-arg	HMDB
(2S)-2-({[(2S)-1-(6-amino-2-{[(2S,3R)-2-amino-1,3-dihydroxybutylidene]amino}hexanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-5-carbamimidamidopentanoate	HMDB
Tuftsin	MeSH

Chemical Formula

C₂₁H₄₀N₈O₆

Average Mass

500.5923 Da

Monoisotopic Mass

500.30708 Da

IUPAC Name

(2S)-2-{[(2S)-1-{6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanoyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

Traditional Name

(2S)-2-{[(2S)-1-{6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanoyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](N)C(=O)NC(CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C21H40N8O6/c1-12(30)16(23)18(32)27-13(6-2-3-9-22)19(33)29-11-5-8-15(29)17(31)28-14(20(34)35)7-4-10-26-21(24)25/h12-16,30H,2-11,22-23H2,1H3,(H,27,32)(H,28,31)(H,34,35)(H4,24,25,26)/t12-,13?,14+,15+,16+/m1/s1

InChI Key

IESDGNYHXIOKRW-NNFXCFJSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Fatty amide
N-acyl-amine
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Guanidine
Amino acid
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organic oxygen compound
Primary aliphatic amine
Carbonyl group
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-3.3	ALOGPS
logP	-5.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	11.9	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	249.98 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	136.78 m³·mol⁻¹	ChemAxon
Polarizability	52.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0005770

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023760

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tuftsin

METLIN ID

Not Available

PubChem Compound

53477795

PDB ID

Not Available

ChEBI ID

88947

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tuftsin (NP0087409)

MOL for NP0087409 (Tuftsin)

3D MOL for NP0087409 (Tuftsin)

3D SDF for NP0087409 (Tuftsin)

3D-SDF for NP0087409 (Tuftsin)

PDB for NP0087409 (Tuftsin)

3D PDB for NP0087409 (Tuftsin)

SMILES for NP0087409 (Tuftsin)

INCHI for NP0087409 (Tuftsin)

Structure for NP0087409 (Tuftsin)

3D Structure for NP0087409 (Tuftsin)