MiMeDB: Showing metabocard for UDP-4-Deoxy-4-formamido-beta-L-arabinose (MMDBc0031791)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:27 UTC

Update Date

2022-08-31 18:24:46 UTC

Metabolite ID

MMDBc0031791

Metabolite Identification

Common Name

UDP-4-Deoxy-4-formamido-beta-L-arabinose

Description

UDP-4-Deoxy-4-formamido-beta-L-arabinose is an intermediate in the polymixin resistance pathway. It is a substrate for the enzyme Bifunctional polymyxin resistance protein ArnA that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto-arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4-amino-4-deoxy-L-arabinose (UDP-L-Ara4N) to form UDP-L-4-formamido-arabinose (UDP-L-Ara4FN). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides. Some Gram-negative bacteria, specifically Salmonella typhimurium and Escherichia coli, can become resistant to polymyxin by the modification of their lipid A structure via the attachment of 4-amino-4-deoxy-L-arabinopyranose (L-Ara4N) groups to one or more phosphate groups. This addition causes an absolute increase in lipid A charge, thus lowering the affinity of positively charged polymyxins.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10101211212D          

 44 46  0  0  0  0            999 V2000
   -2.4757    3.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893    9.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8585   10.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   10.6442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7615    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2962    3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477   11.1962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    7.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0964    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0631   10.9413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1468    5.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   10.8991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    4.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    5.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6431   10.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   12.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   11.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    6.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    8.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    7.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    9.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    8.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5047    9.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    7.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    5.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069    9.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    8.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793    8.0105    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    9.0724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739   10.0922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    7.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323   11.4512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    7.7819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   11.7483    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    6.0381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   10.6864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  1  0  0  0
  8  1  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 16  5  2  0  0  0  0
  6 16  1  1  0  0  0
 17  8  2  0  0  0  0
 17 15  1  0  0  0  0
 18  2  1  0  0  0  0
 13 18  1  1  0  0  0
 18 15  1  0  0  0  0
  5 19  1  4  0  0  0
 20  8  1  0  0  0  0
  9 21  1  1  0  0  0
 10 22  1  6  0  0  0
 11 23  1  6  0  0  0
 12 24  1  6  0  0  0
 25 15  2  0  0  0  0
 30  3  1  0  0  0  0
 30 14  1  0  0  0  0
 31  4  1  0  0  0  0
 32  7  1  0  0  0  0
 32 13  1  0  0  0  0
 14 33  1  6  0  0  0
 35 26  1  0  0  0  0
 35 27  2  0  0  0  0
 35 31  1  0  0  0  0
 35 34  1  0  0  0  0
 36 28  1  0  0  0  0
 36 29  2  0  0  0  0
 36 33  1  0  0  0  0
 36 34  1  0  0  0  0
  6 37  1  6  0  0  0
  7 38  1  6  0  0  0
  9 39  1  6  0  0  0
 10 40  1  1  0  0  0
 11 41  1  1  0  0  0
 12 42  1  1  0  0  0
 13 43  1  6  0  0  0
 14 44  1  1  0  0  0
M  END


  Mrv0541 10101211212D          

 44 46  0  0  0  0            999 V2000
   -2.4757    3.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893    9.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8585   10.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   10.6442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7615    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2962    3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477   11.1962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    7.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0964    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0631   10.9413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1468    5.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   10.8991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    4.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    5.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6431   10.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   12.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   11.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    6.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    8.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    7.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    9.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    8.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5047    9.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    7.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    5.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069    9.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    8.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793    8.0105    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    9.0724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739   10.0922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    7.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323   11.4512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    7.7819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   11.7483    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    6.0381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   10.6864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  1  0  0  0
  8  1  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 16  5  2  0  0  0  0
  6 16  1  1  0  0  0
 17  8  2  0  0  0  0
 17 15  1  0  0  0  0
 18  2  1  0  0  0  0
 13 18  1  1  0  0  0
 18 15  1  0  0  0  0
  5 19  1  4  0  0  0
 20  8  1  0  0  0  0
  9 21  1  1  0  0  0
 10 22  1  6  0  0  0
 11 23  1  6  0  0  0
 12 24  1  6  0  0  0
 25 15  2  0  0  0  0
 30  3  1  0  0  0  0
 30 14  1  0  0  0  0
 31  4  1  0  0  0  0
 32  7  1  0  0  0  0
 32 13  1  0  0  0  0
 14 33  1  6  0  0  0
 35 26  1  0  0  0  0
 35 27  2  0  0  0  0
 35 31  1  0  0  0  0
 35 34  1  0  0  0  0
 36 28  1  0  0  0  0
 36 29  2  0  0  0  0
 36 33  1  0  0  0  0
 36 34  1  0  0  0  0
  6 37  1  6  0  0  0
  7 38  1  6  0  0  0
  9 39  1  6  0  0  0
 10 40  1  1  0  0  0
 11 41  1  1  0  0  0
 12 42  1  1  0  0  0
 13 43  1  6  0  0  0
 14 44  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031791

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N=CO)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C15H23N3O16P2/c19-5-16-6-3-30-14(12(24)9(6)21)33-36(28,29)34-35(26,27)31-4-7-10(22)11(23)13(32-7)18-2-1-8(20)17-15(18)25/h1-2,5-7,9-14,21-24H,3-4H2,(H,16,19)(H,26,27)(H,28,29)(H,17,20,25)/t6-,7+,9-,10+,11+,12+,13+,14+/m0/s1

> <INCHI_KEY>
QGYFHZBDXXNYAX-RTXATJJPSA-N

> <FORMULA>
C15H23N3O16P2

> <MOLECULAR_WEIGHT>
563.3011

> <EXACT_MASS>
563.055354727

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
46.42259976804134

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxyoxan-3-yl]carboximidic acid

> <ALOGPS_LOGP>
-1.49

> <JCHEM_LOGP>
-4.557414913384654

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.2750550497362765

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6080616156571894

> <JCHEM_PKA_STRONGEST_BASIC>
2.5283250672077284

> <JCHEM_POLAR_SURFACE_AREA>
287.16

> <JCHEM_REFRACTIVITY>
107.94749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
udp-L-ara4FN

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-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  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+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  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   36  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   37  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    8                                                       
CONECT    2    1   18                                                       
CONECT    3    6   30                                                       
CONECT    4    7   31                                                       
CONECT    5   16   19                                                       
CONECT    6    3    9   16   37                                             
CONECT    7    4   10   32   38                                             
CONECT    8    1   17   20                                                  
CONECT    9    6   12   21   39                                             
CONECT   10    7   11   22   40                                             
CONECT   11   10   13   23   41                                             
CONECT   12    9   14   24   42                                             
CONECT   13   11   18   32   43                                             
CONECT   14   12   30   33   44                                             
CONECT   15   17   18   25                                                  
CONECT   16    5    6                                                       
CONECT   17    8   15                                                       
CONECT   18    2   13   15                                                  
CONECT   19    5                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   15                                                            
CONECT   26   35                                                            
CONECT   27   35                                                            
CONECT   28   36                                                            
CONECT   29   36                                                            
CONECT   30    3   14                                                       
CONECT   31    4   35                                                       
CONECT   32    7   13                                                       
CONECT   33   14   36                                                       
CONECT   34   35   36                                                       
CONECT   35   26   27   31   34                                             
CONECT   36   28   29   33   34                                             
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

Synonyms

Value	Source
UDP-beta-L-Ara4fn	ChEBI
Uridine 5'-diphospho-beta-(4-deoxy-4-formamido-L-arabinose)	ChEBI
UDP-4-Deoxy-4-formamido-beta-L-arabinopyranose	Kegg
UDP-b-L-Ara4fn	Generator
UDP-Β-L-ara4fn	Generator
Uridine 5'-diphospho-b-(4-deoxy-4-formamido-L-arabinose)	Generator
Uridine 5'-diphospho-β-(4-deoxy-4-formamido-L-arabinose)	Generator
UDP-4-Deoxy-4-formamido-b-L-arabinopyranose	Generator
UDP-4-Deoxy-4-formamido-β-L-arabinopyranose	Generator
UDP-4-Deoxy-4-formamido-b-L-arabinose	Generator
UDP-4-Deoxy-4-formamido-β-L-arabinose	Generator

Molecular Formula

C₁₅H₂₃N₃O₁₆P₂

Average Mass

563.3011

Monoisotopic Mass

563.055354727

IUPAC Name

N-[(3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxyoxan-3-yl]carboximidic acid

Traditional Name

udp-L-ara4FN

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N=CO)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C15H23N3O16P2/c19-5-16-6-3-30-14(12(24)9(6)21)33-36(28,29)34-35(26,27)31-4-7-10(22)11(23)13(32-7)18-2-1-8(20)17-15(18)25/h1-2,5-7,9-14,21-24H,3-4H2,(H,16,19)(H,26,27)(H,28,29)(H,17,20,25)/t6-,7+,9-,10+,11+,12+,13+,14+/m0/s1

InChI Key

QGYFHZBDXXNYAX-RTXATJJPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside diphosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Vinylogous amide
Tetrahydrofuran
Heteroaromatic compound
Urea
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic nitrogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-amino sugar (CHEBI:47027 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-4.6	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	2.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	287.16 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	107.95 m³·mol⁻¹	ChemAxon
Polarizability	46.42 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_21) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901120000-8c46a03f73f7f398767f	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3911000000-b4cab5f793e5beaf70ef	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4900000000-6d1bce8d76549b349101	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-6901140000-33d8688917904f4103f1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06r6-7906010000-dffdf6a6c3314c45f1ab	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06r6-5901000000-6169fa44322865858538	2015-09-15	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	76	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; River trout	Unknown
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16154

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17756768

PDB ID

Not Available

ChEBI ID

47027

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for UDP-4-Deoxy-4-formamido-beta-L-arabinose (MMDBc0031791)

MOL for #<Metabolite:0x00007fecc809a7d8>

3D MOL for #<Metabolite:0x00007fecc809a7d8>

3D SDF for #<Metabolite:0x00007fecc809a7d8>

3D-SDF for #<Metabolite:0x00007fecc809a7d8>

PDB for #<Metabolite:0x00007fecc809a7d8>

3D PDB for #<Metabolite:0x00007fecc809a7d8>

SMILES for #<Metabolite:0x00007fecc809a7d8>

INCHI for #<Metabolite:0x00007fecc809a7d8>

Structure for #<Metabolite:0x00007fecc809a7d8>

3D Structure for #<Metabolite:0x00007fecc809a7d8>