NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid (NP0314075)

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Record Information

Version

2.0

Created at

2022-09-11 11:59:12 UTC

Updated at

2022-09-11 11:59:13 UTC

NP-MRD ID

NP0314075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid

Description

SCHEMBL17813729 belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. (2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid is found in Streptomyces tanashiensis. Based on a literature review very few articles have been published on SCHEMBL17813729.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213592D          

 37 39  0  0  1  0            999 V2000
    0.6710   -5.1170    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


  Mrv1652309112213592D          

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 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
  5 21  1  0  0  0  0
 21 22  1  4  0  0  0
 21 23  2  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 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  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 26 34  1  0  0  0  0
 29 34  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H](NP(O)(=O)OC1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18-,19+,20+,23?/m0/s1

> <INCHI_KEY>
ZPHBZEQOLSRPAK-QIHRTDBRSA-N

> <FORMULA>
C23H34N3O10P

> <MOLECULAR_WEIGHT>
543.51

> <EXACT_MASS>
543.198181305

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.38938900035286

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-1-hydroxy-2-{[hydroxy({[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]amino}-4-methylpentylidene]amino}-3-(1H-indol-3-yl)propanoic acid

> <JCHEM_LOGP>
0.9786360333333338

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9671643264796432

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4872987313524053

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122134906304293

> <JCHEM_POLAR_SURFACE_AREA>
214.15999999999997

> <JCHEM_REFRACTIVITY>
129.4614

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-1-hydroxy-2-{[hydroxy([(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1H-indol-3-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.253  -9.552   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.284  -8.727   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -3.821  -7.903   0.000  0.00  0.00           N+0
HETATM    7  P   UNK     0      -4.297  -9.368   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      -2.832  -9.844   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -5.762  -8.892   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.773 -10.832   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.279 -11.153   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.755 -12.617   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -8.261 -12.937   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.737 -14.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.292 -11.793   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.798 -12.113   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.816 -10.328   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.846  -9.184   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -7.310 -10.008   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.834  -8.544   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.650  -4.013   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       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20                                                  
CONECT   20   19                                                            
CONECT   21    5   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   26   29                                                  
CONECT   35   24   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₄N₃O₁₀P

Average Mass

543.5100 Da

Monoisotopic Mass

543.19818 Da

IUPAC Name

(2S)-2-{[(2S)-1-hydroxy-2-{[hydroxy({[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]amino}-4-methylpentylidene]amino}-3-(1H-indol-3-yl)propanoic acid

Traditional Name

(2S)-2-{[(2S)-1-hydroxy-2-{[hydroxy([(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H](NP(O)(=O)OC1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18-,19+,20+,23?/m0/s1

InChI Key

ZPHBZEQOLSRPAK-QIHRTDBRSA-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
Streptomyces tanashiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Leucine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Hexose monosaccharide
Indolyl carboxylic acid derivative
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Phosphoric monoester monoamide
Fatty amide
Monosaccharide
N-acyl-amine
Fatty acyl
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Substituted pyrrole
Benzenoid
Organic phosphoric acid amide
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Organoheterocyclic compound
Carboxylic acid
Azacycle
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
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	0.98	ChemAxon
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	214.16 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	129.46 m³·mol⁻¹	ChemAxon
Polarizability	52.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

58866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65400

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid (NP0314075)

MOL for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D MOL for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D SDF for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D-SDF for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

PDB for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D PDB for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

SMILES for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

INCHI for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

Structure for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D Structure for NP0314075 ((2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy([(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]amino}-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoic acid)