Np mrd loader

Showing NP-Card for UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine (NP0334388)

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Record Information
Version2.0
Created at2024-09-09 23:27:17 UTC
Updated at2024-09-09 23:27:17 UTC
NP-MRD IDNP0334388
Secondary Accession NumbersNone
Natural Product Identification
Common NameUDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine
DescriptionUdp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine can be found in a number of food items such as chickpea, pineapple, sea-buckthornberry, and savoy cabbage, which makes udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine a potential biomarker for the consumption of these food products. Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine may be a unique E.Coli metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)


  Mrv0541 07301213422D          

 62 64  0  0  0  0            999 V2000
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M  CHG  1  35  -1
M  END
Download

3D MOL for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

Download
3D SDF for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

  Mrv0541 07301213422D          

 62 64  0  0  0  0            999 V2000
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M  CHG  1  35  -1
M  END
> <DATABASE_ID>
NP0334388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@]1([H])[C@@]([H])(N)[C@@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)O[C@]([H])(CO)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C29H51N3O18P2/c1-2-3-4-5-6-7-8-9-10-11-17(34)14-21(36)48-26-22(30)28(47-18(15-33)24(26)38)49-52(43,44)50-51(41,42)45-16-19-23(37)25(39)27(46-19)32-13-12-20(35)31-29(32)40/h12-13,17-19,22-28,33-34,37-39H,2-11,14-16,30H2,1H3,(H,41,42)(H,43,44)(H,31,35,40)/p-1/t17-,18-,19-,22-,23-,24-,25-,26-,27-,28-/m1/s1

> <INCHI_KEY>
ZFPNNOXCEDQJQS-SSVOXRMNSA-M

> <FORMULA>
C29H50N3O18P2

> <MOLECULAR_WEIGHT>
790.6641

> <EXACT_MASS>
790.256459835

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
75.93970468831516

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-1.1386886310025335

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.148549807075473

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7198793192257793

> <JCHEM_PKA_STRONGEST_BASIC>
8.466845397719524

> <JCHEM_POLAR_SURFACE_AREA>
329.95000000000005

> <JCHEM_REFRACTIVITY>
184.89020000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-olate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)
Download
PDB for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)
HEADER    PROTEIN                                 30-JUL-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   52  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   53  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   17                                                       
CONECT   12   13   20                                                       
CONECT   13   12   32                                                       
CONECT   14   17   21                                                       
CONECT   15   18   33                                                       
CONECT   16   19   45                                                       
CONECT   17   11   14   34   53                                             
CONECT   18   15   24   47   54                                             
CONECT   19   16   23   46   55                                             
CONECT   20   12   31   35                                                  
CONECT   21   14   36   48                                                  
CONECT   22   26   28   30   56                                             
CONECT   23   19   25   37   57                                             
CONECT   24   18   26   38   58                                             
CONECT   25   23   27   39   59                                             
CONECT   26   22   24   48   60                                             
CONECT   27   25   32   46   61                                             
CONECT   28   22   47   49   62                                             
CONECT   29   31   32   40                                                  
CONECT   30   22                                                            
CONECT   31   20   29                                                       
CONECT   32   13   27   29                                                  
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   20                                                            
CONECT   36   21                                                            
CONECT   37   23                                                            
CONECT   38   24                                                            
CONECT   39   25                                                            
CONECT   40   29                                                            
CONECT   41   51                                                            
CONECT   42   51                                                            
CONECT   43   52                                                            
CONECT   44   52                                                            
CONECT   45   16   51                                                       
CONECT   46   19   27                                                       
CONECT   47   18   28                                                       
CONECT   48   21   26                                                       
CONECT   49   28   52                                                       
CONECT   50   51   52                                                       
CONECT   51   41   42   45   50                                             
CONECT   52   43   44   49   50                                             
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   28                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  128    0
END

Download
3D PDB for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)
Download
SMILES for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)
[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@]1([H])[C@@]([H])(N)[C@@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)O[C@]([H])(CO)[C@@]1([H])O
Download
INCHI for NP0334388 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)
InChI=1S/C29H51N3O18P2/c1-2-3-4-5-6-7-8-9-10-11-17(34)14-21(36)48-26-22(30)28(47-18(15-33)24(26)38)49-52(43,44)50-51(41,42)45-16-19-23(37)25(39)27(46-19)32-13-12-20(35)31-29(32)40/h12-13,17-19,22-28,33-34,37-39H,2-11,14-16,30H2,1H3,(H,41,42)(H,43,44)(H,31,35,40)/p-1/t17-,18-,19-,22-,23-,24-,25-,26-,27-,28-/m1/s1
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View in JSmol
Synonyms
ValueSource
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-alpha-D-glucosamineChEBI
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-a-D-glucosamineGenerator
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-α-D-glucosamineGenerator
Chemical FormulaC29H50N3O18P2
Average Mass790.6641 Da
Monoisotopic Mass790.25646 Da
IUPAC Name1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate
Traditional Name1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-olate
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@]1([H])[C@@]([H])(N)[C@@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)O[C@]([H])(CO)[C@@]1([H])O
InChI Identifier
InChI=1S/C29H51N3O18P2/c1-2-3-4-5-6-7-8-9-10-11-17(34)14-21(36)48-26-22(30)28(47-18(15-33)24(26)38)49-52(43,44)50-51(41,42)45-16-19-23(37)25(39)27(46-19)32-13-12-20(35)31-29(32)40/h12-13,17-19,22-28,33-34,37-39H,2-11,14-16,30H2,1H3,(H,41,42)(H,43,44)(H,31,35,40)/p-1/t17-,18-,19-,22-,23-,24-,25-,26-,27-,28-/m1/s1
InChI KeyZFPNNOXCEDQJQS-SSVOXRMNSA-M
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds  
Super ClassNucleosides, nucleotides, and analogues  
ClassPyrimidine nucleotides  
Sub ClassPyrimidine nucleotide sugars  
Direct ParentPyrimidine nucleotide sugars  
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
    • 

  • Pyrimidine ribonucleoside diphosphate
    • 

  • Saccharolipid
    • 

  • Pentose phosphate
    • 

  • Pentose-5-phosphate
    • 

  • Glycosyl compound
    • 

  • N-glycosyl compound
    • 

  • Monosaccharide phosphate
    • 

  • Organic pyrophosphate
    • 

  • Beta-hydroxy acid
    • 

  • Fatty acid ester
    • 

  • Pyrimidone
    • 

  • Amino saccharide
    • 

  • Hydropyrimidine
    • 

  • Hydroxy acid
    • 

  • Monosaccharide
    • 

  • Organic phosphoric acid derivative
    • 

  • Oxane
    • 

  • Phosphoric acid ester
    • 

  • Fatty acyl
    • 

  • Pyrimidine
    • 

  • Alkyl phosphate
    • 

  • Tetrahydrofuran
    • 

  • Vinylogous amide
    • 

  • Heteroaromatic compound
    • 

  • Urea
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Amino acid or derivatives
    • 

  • Lactam
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Primary amine
    • 

  • Primary aliphatic amine
    • 

  • Hydrocarbon derivative
    • 

  • Amine
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Primary alcohol
    • 

  • Organic anion
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • UDP-3-O-[(3R)-3-hydroxytetradecanoyl]-D-glucosamine(1-) (CHEBI:71573  )
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.5ALOGPS
logP-1.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area329.95 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity184.89 m³·mol⁻¹ChemAxon
Polarizability75.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031238  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDUDP-OHMYR-GLUCOSAMINE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25244806  
PDB IDNot Available
ChEBI ID71573  
Good Scents IDNot Available
References
General ReferencesNot Available