NP-MRD: Showing NP-Card for L-Histidinol phosphate (NP0054979)

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Record Information

Version

2.0

Created at

2022-04-28 01:10:05 UTC

Updated at

2022-04-28 01:10:05 UTC

NP-MRD ID

NP0054979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Histidinol phosphate

Description

L-histidinol phosphate belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. L-histidinol phosphate is a very strong basic compound (based on its pKa). L-histidinol phosphate exists in both E. Coli (prokaryote) and yeast (eukaryote). Within yeast, L-histidinol phosphate participates in a number of enzymatic reactions. In particular, oxoglutaric acid and L-histidinol phosphate can be biosynthesized from imidazole acetol-phosphate and L-glutamic acid through the action of the enzyme histidinol-phosphate aminotransferase. In addition, L-histidinol phosphate can be converted into L-histidinol; which is mediated by the enzyme histidinol-phosphatase. L-Histidinol phosphate is found in Arabidopsis thaliana and Escherichia coli. In yeast, L-histidinol phosphate is involved in the metabolic pathway called histidine biosynthesis pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02241222062D          
 
 14 14  0  0  1  0            999 V2000
   18.8444   -9.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1361   -9.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4243   -9.9859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.7154   -9.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0036   -9.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1706   -9.9849    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.1663   -9.1535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3392   -9.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1663  -10.8163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4226  -10.8172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9353  -10.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7506  -10.9829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1635  -10.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6035   -9.6436    0.0000 N   0  0  0  0  0  0  0  0  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
  1  2  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3 10  1  6  0  0  0
  1 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H](COP(O)(O)=O)CC1=CNC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N3O4P/c7-5(3-13-14(10,11)12)1-6-2-8-4-9-6/h2,4-5H,1,3,7H2,(H,8,9)(H2,10,11,12)/t5-/m0/s1

> <INCHI_KEY>
CWNDERHTHMWBSI-YFKPBYRVSA-N

> <FORMULA>
C6H12N3O4P

> <MOLECULAR_WEIGHT>
221.1509

> <EXACT_MASS>
221.056542399

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
19.40789171621973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2-amino-3-(1H-imidazol-4-yl)propoxy]phosphonic acid

> <ALOGPS_LOGP>
-1.38

> <JCHEM_LOGP>
-2.9241371802886

> <ALOGPS_LOGS>
-0.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.733002703308064

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5852216576798401

> <JCHEM_PKA_STRONGEST_BASIC>
9.668584795241904

> <JCHEM_POLAR_SURFACE_AREA>
121.46

> <JCHEM_REFRACTIVITY>
48.498799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-histidinol phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      35.176 -18.640   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.854 -17.885   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.525 -18.640   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.202 -17.885   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      29.873 -18.640   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0      28.318 -18.638   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0      28.310 -17.087   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      26.767 -18.638   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      28.310 -20.190   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      32.522 -20.192   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      35.346 -20.185   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      36.868 -20.501   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      37.639 -19.152   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      36.593 -18.001   0.000  0.00  0.00           N+0
CONECT    1    2   11   14                                                  
CONECT    2    1    3                                                       
CONECT    3    4    2   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    3                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    1                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
PHOSPHORIC ACID mono-[2-amino-3-(3H-imidazol-4-yl)-propyl]ester	ChEBI
PHOSPHate mono-[2-amino-3-(3H-imidazol-4-yl)-propyl]ester	Generator
L-Histidinol phosphoric acid	Generator
L-Histidinol-phosphoric acid	Generator

Chemical Formula

C₆H₁₂N₃O₄P

Average Mass

221.1509 Da

Monoisotopic Mass

221.05654 Da

IUPAC Name

[(2S)-2-amino-3-(1H-imidazol-4-yl)propoxy]phosphonic acid

Traditional Name

L-histidinol phosphate

CAS Registry Number

Not Available

SMILES

N[C@H](COP(O)(O)=O)CC1=CNC=N1

InChI Identifier

InChI=1S/C6H12N3O4P/c7-5(3-13-14(10,11)12)1-6-2-8-4-9-6/h2,4-5H,1,3,7H2,(H,8,9)(H2,10,11,12)/t5-/m0/s1

InChI Key

CWNDERHTHMWBSI-YFKPBYRVSA-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
Arabidopsis thaliana	Plant	KNApSAcK
Escherichia coli	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phosphoethanolamines

Alternative Parents

Substituents

Phosphoethanolamine
Monoalkyl phosphate
Aralkylamine
Alkyl phosphate
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phosphoethanolamine (CHEBI:16996 )

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	-1.4	ALOGPS
logP	-2.9	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	48.5 m³·mol⁻¹	ChemAxon
Polarizability	19.41 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB03997

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030967

KNApSAcK ID

C00007480

Chemspider ID

Not Available

KEGG Compound ID

C01100

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439398

PDB ID

Not Available

ChEBI ID

16996

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for L-Histidinol phosphate (NP0054979)

MOL for NP0054979 (L-Histidinol phosphate)

3D MOL for NP0054979 (L-Histidinol phosphate)

3D SDF for NP0054979 (L-Histidinol phosphate)

3D-SDF for NP0054979 (L-Histidinol phosphate)

PDB for NP0054979 (L-Histidinol phosphate)

3D PDB for NP0054979 (L-Histidinol phosphate)

SMILES for NP0054979 (L-Histidinol phosphate)

INCHI for NP0054979 (L-Histidinol phosphate)

Structure for NP0054979 (L-Histidinol phosphate)

3D Structure for NP0054979 (L-Histidinol phosphate)