NP-MRD: Showing NP-Card for N-Ribosylhistidine (NP0086869)

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Record Information

Version

1.0

Created at

2022-05-11 16:33:17 UTC

Updated at

2022-05-11 16:33:18 UTC

NP-MRD ID

NP0086869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Ribosylhistidine

Description

N-Ribosylhistidine, also known as his-R, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Ribosylhistidine is a very strong basic compound (based on its pKa). It was first documented in 1985 (PMID: 2992472). N-Ribosylhistidine, with regard to humans, has been linked to the inborn metabolic disorder histidinemia.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    5.4485   -1.3633   -0.7767 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2497   -0.5533   -0.7168 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2851   -1.2656    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -0.5167    0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8459   -0.5976   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    0.2862    0.1323 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665    0.5442   -0.3105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2082    0.9956    0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4265    1.0778    0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5905    1.1653    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618    0.0601    1.8366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -0.1317   -0.8451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7246    0.3294   -2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -0.7025   -0.7498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6692   -1.2041   -1.9481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558    0.9185    1.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7961    0.4268    1.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6150    0.7832   -0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7952    1.0384    0.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6773    1.8020   -0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1963   -2.3036   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8660   -1.4155    0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7933   -0.4977   -1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118   -1.3763    1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -2.2897   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.2800   -1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384    1.2762   -1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4011    2.0252   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5286    2.1156    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5190    1.2077    0.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4505   -0.5060    1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756   -0.8583   -0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543    0.3396   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465   -1.4598    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7697   -2.1885   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609    1.6946    1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586    2.4238    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6 16  1  0
 16 17  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 18  1  0
 18 20  1  0
 18 19  2  0
 17  4  1  0
 14  7  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
 16 36  1  0
  7 27  1  6
  9 28  1  6
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  1
 13 33  1  0
 14 34  1  1
 15 35  1  0
 20 37  1  0
M  END

Untitled Document-6
  Mrv0541 02231219212D          

 20 21  0  0  0  0            999 V2000
    2.0652   -0.9083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7326   -0.4234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4777    0.3613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6527    0.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -0.4234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4668   -1.4629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582   -1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131   -0.6783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543   -0.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218   -0.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064   -0.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -0.9754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9041   -0.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5172   -1.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0756    0.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480   -1.7824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626    1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -1.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5172   -0.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270    1.7824    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  6  1  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  0  0  0  0
 13 15  2  0  0  0  0
 12 16  1  6  0  0  0
  5  8  1  6  0  0  0
  3 17  1  6  0  0  0
  1 18  1  1  0  0  0
  2 19  1  1  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H17N3O6/c12-6(11(18)19)1-5-2-14(4-13-5)10-9(17)8(16)7(3-15)20-10/h2,4,6-10,15-17H,1,3,12H2,(H,18,19)/t6-,7+,8+,9+,10+/m0/s1

> <INCHI_KEY>
TTYCFBAOLXCFAB-VAPHQMJDSA-N

> <FORMULA>
C11H17N3O6

> <MOLECULAR_WEIGHT>
287.2692

> <EXACT_MASS>
287.111735291

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
27.153659710548624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}propanoic acid

> <ALOGPS_LOGP>
-2.96

> <JCHEM_LOGP>
-4.85220119088643

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.456468815494357

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5295408048889358

> <JCHEM_PKA_STRONGEST_BASIC>
9.244859670190673

> <JCHEM_POLAR_SURFACE_AREA>
151.05999999999997

> <JCHEM_REFRACTIVITY>
64.0896

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
his-R

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-6                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       3.855  -1.695   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.101  -0.790   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.625   0.674   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.085   0.674   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.609  -0.790   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.871  -2.731   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.669  -2.731   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.144  -1.266   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.101  -0.361   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.347  -1.266   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.812  -0.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.956  -1.821   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.421  -1.345   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.565  -2.375   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -5.741   0.161   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      -3.636  -3.327   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.530   1.920   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.855  -3.235   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.565  -1.266   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.904   3.327   0.000  0.00  0.00           O+0
CONECT    1    2    5   18                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    8                                                  
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    5                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17    3   20                                                       
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
His-R	HMDB
N(Tau)-ribosylhistidine	HMDB
(2S)-2-Amino-3-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}propanoate	HMDB

Chemical Formula

C₁₁H₁₇N₃O₆

Average Mass

287.2692 Da

Monoisotopic Mass

287.11174 Da

IUPAC Name

(2S)-2-amino-3-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}propanoic acid

Traditional Name

his-R

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=CN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C11H17N3O6/c12-6(11(18)19)1-5-2-14(4-13-5)10-9(17)8(16)7(3-15)20-10/h2,4,6-10,15-17H,1,3,12H2,(H,18,19)/t6-,7+,8+,9+,10+/m0/s1

InChI Key

TTYCFBAOLXCFAB-VAPHQMJDSA-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 histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Imidazole ribonucleoside
Glycosyl compound
N-glycosyl compound
Alpha-amino acid
Pentose monosaccharide
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
Monosaccharide
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Amino acid
Secondary alcohol
Carboxylic acid
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Primary amine
Organic oxide
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Amine
Hydrocarbon derivative
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	ALOGPS
logP	-4.9	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.53	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	151.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.09 m³·mol⁻¹	ChemAxon
Polarizability	27.15 Å³	ChemAxon
Number of Rings	2	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

HMDB0002089

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022840

KNApSAcK ID

Not Available

Chemspider ID

112711

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6481

PubChem Compound

126923

PDB ID

Not Available

ChEBI ID

90055

Good Scents ID

Not Available

References

General References

Imamura I, Watanabe T, Wada H: Formation of N tau-ribosylhistidine, a novel histidine derivative found in the urine in histidinemia, from histidine and NAD(P)+ catalyzed by an NAD(P)+ glycohydrolase system. Biochem Biophys Res Commun. 1985 Jul 31;130(2):501-7. doi: 10.1016/0006-291x(85)90445-0. [PubMed:2992472 ]

Showing NP-Card for N-Ribosylhistidine (NP0086869)

MOL for NP0086869 (N-Ribosylhistidine)

3D MOL for NP0086869 (N-Ribosylhistidine)

3D SDF for NP0086869 (N-Ribosylhistidine)

3D-SDF for NP0086869 (N-Ribosylhistidine)

PDB for NP0086869 (N-Ribosylhistidine)

3D PDB for NP0086869 (N-Ribosylhistidine)

SMILES for NP0086869 (N-Ribosylhistidine)

INCHI for NP0086869 (N-Ribosylhistidine)

Structure for NP0086869 (N-Ribosylhistidine)

3D Structure for NP0086869 (N-Ribosylhistidine)