NP-MRD: Showing NP-Card for Uridine diphosphate-N-acetylglucosamine (NP0000283)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:14:17 UTC

NP-MRD ID

NP0000283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uridine diphosphate-N-acetylglucosamine

Description

Uridine diphosphate-N-acetylglucosamine (uridine 5'-diphosphate-GlcNAc, or UDP-Glc-NAc) is an acetylated aminosugar nucleotide. UDP-GlcNAc is the donor substrate for modification of nucleocytoplasmic proteins at serine and threonine residues with N-acetylglucosamine (O-GlcNAc). Nutrient sensing in mammals is done through the hexosamine biosynthetic pathway (HSP), which produces uridine 5'-diphospho-N-acetylglucosamine (UDP-Glc-NAc) as its end product. Mammals respond to nutrient excess by activating O-GlcNAcylation (addition of O-linked N-acetylglucosamine). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. (PMID: 16317114 ) Due to the chemical makeup of UDP-GlcNAc, it is well positioned to serve as a glucose sensor in that it is a high-energy compound that requires and/or responds to glucose, amino acid, fatty acid and nucleotide metabolism for synthesis. Elevated levels of O-GlcNAc have an effect on insulin-stimulated glucose uptake. (PMID: 12678487 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309152018162D          

 39 41  0  0  0  0            999 V2000
 9996.7329 9998.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5237 9998.1631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.031310000.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5540 9998.7852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10000.460310000.0213    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9994.123510001.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3737 9999.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.047910000.7358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.872710000.7358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.285110000.0234    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.0006 9999.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.872710000.7399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3  5  1  0  0  0  0
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 37 15  1  1  0  0  0
 38 17  1  6  0  0  0
 34 18  1  6  0  0  0
 39 21  1  1  0  0  0
M  END

HMDB0000290
     RDKit          3D
Uridine diphosphate-N-acetylglucosamine
 66 68  0  0  0  0  0  0  0  0999 V2000
   -6.3921   -4.2518    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3530   -2.7438    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5777   -0.3813   -1.0078 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2482   -0.7684   -2.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -1.6747   -0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541    1.0543   -0.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922    0.9571    0.8006 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.5214    1.5147    1.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4933   -0.7095    1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    1.7160    0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329    0.8400    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4287    0.1818    0.1871 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4179    0.7599   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4357   -0.1854   -0.6056 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7686    0.3633   -0.4829 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5568    1.5454    0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5056    3.4039    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    3.8826    0.9203 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6315    0.1400   -0.9197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8550   -0.3554   -1.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4177   -4.5770   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2207   -4.4864   -0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6639    2.1016   -0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9690    4.0707   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1200    3.3717    1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4375    1.5932    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8664    0.0880   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7288   -1.0379   -1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
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 22 23  1  0
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  6 32  1  0
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 30 17  1  0
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  1 40  1  0
  1 41  1  0
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  4 43  1  0
  5 44  1  1
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 36 63  1  1
 37 64  1  0
 38 65  1  6
 39 66  1  0
M  END


  Mrv1652309152018162D          

 39 41  0  0  0  0            999 V2000
 9996.7329 9998.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5237 9998.1631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.031310000.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5540 9998.7852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10000.460310000.0213    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9994.123510001.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3737 9999.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10004.4275 9998.7893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.1430 9998.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.8564 9999.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.427510002.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.8564 9998.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.1430 9997.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.856410001.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.143010002.4988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.552710001.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10004.428210001.2615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  3  5  1  0  0  0  0
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 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 31  1  1  1  0  0  0
 30 27  1  6  0  0  0
 32  2  1  1  0  0  0
 33  3  1  6  0  0  0
 34 39  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 12  1  1  0  0  0
 37 15  1  1  0  0  0
 38 17  1  6  0  0  0
 34 18  1  6  0  0  0
 39 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0000283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1

> <INCHI_KEY>
LFTYTUAZOPRMMI-CFRASDGPSA-N

> <FORMULA>
C17H27N3O17P2

> <MOLECULAR_WEIGHT>
607.3537

> <EXACT_MASS>
607.081569477

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.388706252002585

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.41

> <JCHEM_LOGP>
-5.284643272333334

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1791675779187587

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.737213537795745

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5185279253200745

> <JCHEM_POLAR_SURFACE_AREA>
300.40999999999997

> <JCHEM_REFRACTIVITY>
117.55709999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
udp-N-acetyl-α-D-glucosamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000290
     RDKit          3D
Uridine diphosphate-N-acetylglucosamine
 66 68  0  0  0  0  0  0  0  0999 V2000
   -6.3921   -4.2518    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3530   -2.7438    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4513   -2.2142    0.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549   -2.0364    0.1332 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0637   -0.6301    0.3085 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6784   -0.1157    0.4589 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2171    0.0381   -0.8804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777   -0.3813   -1.0078 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2482   -0.7684   -2.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -1.6747   -0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541    1.0543   -0.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922    0.9571    0.8006 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.5214    1.5147    1.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4933   -0.7095    1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    1.7160    0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329    0.8400    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4287    0.1818    0.1871 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4179    0.7599   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4357   -0.1854   -0.6056 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7686    0.3633   -0.4829 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7914   -0.4531   -0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0896   -0.0771   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3583    1.1919   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5568    1.5454    0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3008    1.9894    0.2152 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0239    1.5770    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804    2.3260    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3175   -1.0002    0.7149 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0102   -2.1662    0.6626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372   -1.1566    0.7991 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4621   -2.2485   -0.0165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    1.1814    0.9716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3503    2.0236    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5056    3.4039    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    3.8826    0.9203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6905    1.5813   -0.4079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0255    2.4149   -1.4888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6315    0.1400   -0.9197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8550   -0.3554   -1.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4177   -4.5770   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2207   -4.4864   -0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5474   -4.7211    1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3007   -2.5633   -0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353   -0.3168    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -0.7306    1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9121   -2.3484   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -1.1230    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    0.3317    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916    1.6540    1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611   -0.1335   -0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -0.8796   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5718   -1.4210   -1.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9367   -0.7146   -0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4967    2.9506    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197   -0.3108    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7990   -2.6940    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945   -1.2473    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7323   -1.9741   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6639    2.1016   -0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9690    4.0707   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1200    3.3717    1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2275    4.8555    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4375    1.5932    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9233    2.7481   -1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8664    0.0880   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7288   -1.0379   -1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 19 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  6 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38  5  1  0
 30 17  1  0
 26 20  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  5 44  1  1
  6 45  1  1
 10 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  6
 19 51  1  6
 21 52  1  0
 22 53  1  0
 25 54  1  0
 28 55  1  1
 29 56  1  0
 30 57  1  1
 31 58  1  0
 33 59  1  6
 34 60  1  0
 34 61  1  0
 35 62  1  0
 36 63  1  1
 37 64  1  0
 38 65  1  6
 39 66  1  0
M  END

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  O   UNK     0    8660.5688663.253   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8663.9118663.238   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8664.8588666.706   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8658.3678664.399   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8666.1928665.939   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8667.5268666.706   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0    8655.6978669.018   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8669.2318665.728   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8666.7568668.040   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8668.2968668.040   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0    8670.9328666.710   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0    8672.2688665.942   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8670.1628668.048   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8671.7028668.048   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0    8674.9318664.407   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0    8676.2678663.635   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8677.5998665.942   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8674.9318670.561   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8677.5998664.407   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8676.2678662.095   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8677.5998669.022   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8676.2678671.331   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8658.3658669.018   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8657.0318668.248   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0    8657.0318666.708   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0    8658.3658665.938   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0    8659.6998666.708   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0    8659.6998668.248   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    8662.2728666.860   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0    8661.0268665.955   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8661.5028664.491   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8663.0428664.491   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8663.5188665.955   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8674.9338669.021   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0    8673.5998668.251   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0    8673.5998666.711   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8674.9338665.941   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8676.2668666.711   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8676.2668668.251   0.000  0.00  0.00           C+0
CONECT    1   31                                                            
CONECT    2   32                                                            
CONECT    3    5   33                                                       
CONECT    4   26                                                            
CONECT    5    3    6                                                       
CONECT    6    5    8    9   10                                             
CONECT    7   24                                                            
CONECT    8    6   11                                                       
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11   36                                                       
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   16   37                                                       
CONECT   16   15   19   20                                                  
CONECT   17   38                                                            
CONECT   18   22   34                                                       
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   39                                                            
CONECT   22   18                                                            
CONECT   23   24   28                                                       
CONECT   24   23   25    7                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27    4                                                  
CONECT   27   26   28   30                                                  
CONECT   28   23   27                                                       
CONECT   29   30   33                                                       
CONECT   30   31   29   27                                                  
CONECT   31   30   32    1                                                  
CONECT   32   31   33    2                                                  
CONECT   33   32   29    3                                                  
CONECT   34   39   35   18                                                  
CONECT   35   34   36                                                       
CONECT   36   37   35   12                                                  
CONECT   37   36   38   15                                                  
CONECT   38   37   39   17                                                  
CONECT   39   34   38   21                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

COMPND    HMDB0000290
HETATM    1  C1  UNL     1      -6.392  -4.252   0.174  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.353  -2.744   0.348  1.00  0.00           C  
HETATM    3  O1  UNL     1      -7.451  -2.214   0.689  1.00  0.00           O  
HETATM    4  N1  UNL     1      -5.155  -2.036   0.133  1.00  0.00           N  
HETATM    5  C3  UNL     1      -5.064  -0.630   0.308  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.678  -0.116   0.459  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.217   0.038  -0.880  1.00  0.00           O  
HETATM    8  P1  UNL     1      -1.578  -0.381  -1.008  1.00  0.00           P  
HETATM    9  O3  UNL     1      -1.248  -0.768  -2.433  1.00  0.00           O  
HETATM   10  O4  UNL     1      -1.200  -1.675  -0.027  1.00  0.00           O  
HETATM   11  O5  UNL     1      -0.754   1.054  -0.625  1.00  0.00           O  
HETATM   12  P2  UNL     1       0.092   0.957   0.801  1.00  0.00           P  
HETATM   13  O6  UNL     1      -0.521   1.515   1.975  1.00  0.00           O  
HETATM   14  O7  UNL     1       0.493  -0.710   1.031  1.00  0.00           O  
HETATM   15  O8  UNL     1       1.632   1.716   0.418  1.00  0.00           O  
HETATM   16  C5  UNL     1       2.533   0.840   1.156  1.00  0.00           C  
HETATM   17  C6  UNL     1       3.429   0.182   0.187  1.00  0.00           C  
HETATM   18  O9  UNL     1       4.418   0.760  -0.455  1.00  0.00           O  
HETATM   19  C7  UNL     1       5.436  -0.185  -0.606  1.00  0.00           C  
HETATM   20  N2  UNL     1       6.769   0.363  -0.483  1.00  0.00           N  
HETATM   21  C8  UNL     1       7.791  -0.453  -0.765  1.00  0.00           C  
HETATM   22  C9  UNL     1       9.090  -0.077  -0.567  1.00  0.00           C  
HETATM   23  C10 UNL     1       9.358   1.192  -0.060  1.00  0.00           C  
HETATM   24  O10 UNL     1      10.557   1.545   0.116  1.00  0.00           O  
HETATM   25  N3  UNL     1       8.301   1.989   0.215  1.00  0.00           N  
HETATM   26  C11 UNL     1       7.024   1.577   0.006  1.00  0.00           C  
HETATM   27  O11 UNL     1       6.080   2.326   0.275  1.00  0.00           O  
HETATM   28  C12 UNL     1       5.317  -1.000   0.715  1.00  0.00           C  
HETATM   29  O12 UNL     1       6.010  -2.166   0.663  1.00  0.00           O  
HETATM   30  C13 UNL     1       3.837  -1.157   0.799  1.00  0.00           C  
HETATM   31  O13 UNL     1       3.462  -2.249  -0.016  1.00  0.00           O  
HETATM   32  O14 UNL     1      -3.725   1.181   0.972  1.00  0.00           O  
HETATM   33  C14 UNL     1      -4.350   2.024   0.067  1.00  0.00           C  
HETATM   34  C15 UNL     1      -4.506   3.404   0.659  1.00  0.00           C  
HETATM   35  O15 UNL     1      -3.203   3.883   0.920  1.00  0.00           O  
HETATM   36  C16 UNL     1      -5.690   1.581  -0.408  1.00  0.00           C  
HETATM   37  O16 UNL     1      -6.026   2.415  -1.489  1.00  0.00           O  
HETATM   38  C17 UNL     1      -5.631   0.140  -0.920  1.00  0.00           C  
HETATM   39  O17 UNL     1      -6.855  -0.355  -1.271  1.00  0.00           O  
HETATM   40  H1  UNL     1      -5.418  -4.577  -0.241  1.00  0.00           H  
HETATM   41  H2  UNL     1      -7.221  -4.486  -0.498  1.00  0.00           H  
HETATM   42  H3  UNL     1      -6.547  -4.721   1.147  1.00  0.00           H  
HETATM   43  H4  UNL     1      -4.301  -2.563  -0.159  1.00  0.00           H  
HETATM   44  H5  UNL     1      -5.735  -0.317   1.141  1.00  0.00           H  
HETATM   45  H6  UNL     1      -2.968  -0.731   1.046  1.00  0.00           H  
HETATM   46  H7  UNL     1      -1.912  -2.348  -0.046  1.00  0.00           H  
HETATM   47  H8  UNL     1       0.098  -1.123   1.792  1.00  0.00           H  
HETATM   48  H9  UNL     1       2.073   0.332   1.974  1.00  0.00           H  
HETATM   49  H10 UNL     1       3.192   1.654   1.671  1.00  0.00           H  
HETATM   50  H11 UNL     1       2.661  -0.134  -0.683  1.00  0.00           H  
HETATM   51  H12 UNL     1       5.333  -0.880  -1.408  1.00  0.00           H  
HETATM   52  H13 UNL     1       7.572  -1.421  -1.155  1.00  0.00           H  
HETATM   53  H14 UNL     1       9.937  -0.715  -0.790  1.00  0.00           H  
HETATM   54  H15 UNL     1       8.497   2.951   0.597  1.00  0.00           H  
HETATM   55  H16 UNL     1       5.620  -0.311   1.552  1.00  0.00           H  
HETATM   56  H17 UNL     1       5.799  -2.694   1.487  1.00  0.00           H  
HETATM   57  H18 UNL     1       3.494  -1.247   1.834  1.00  0.00           H  
HETATM   58  H19 UNL     1       2.732  -1.974  -0.612  1.00  0.00           H  
HETATM   59  H20 UNL     1      -3.664   2.102  -0.809  1.00  0.00           H  
HETATM   60  H21 UNL     1      -4.969   4.071  -0.072  1.00  0.00           H  
HETATM   61  H22 UNL     1      -5.120   3.372   1.594  1.00  0.00           H  
HETATM   62  H23 UNL     1      -3.228   4.855   0.742  1.00  0.00           H  
HETATM   63  H24 UNL     1      -6.438   1.593   0.385  1.00  0.00           H  
HETATM   64  H25 UNL     1      -6.923   2.748  -1.343  1.00  0.00           H  
HETATM   65  H26 UNL     1      -4.866   0.088  -1.679  1.00  0.00           H  
HETATM   66  H27 UNL     1      -6.729  -1.038  -1.971  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3    3    4
CONECT    4    5   43
CONECT    5    6   38   44
CONECT    6    7   32   45
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   46
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   47
CONECT   15   16
CONECT   16   17   48   49
CONECT   17   18   30   50
CONECT   18   19
CONECT   19   20   28   51
CONECT   20   21   26
CONECT   21   22   22   52
CONECT   22   23   53
CONECT   23   24   24   25
CONECT   25   26   54
CONECT   26   27   27
CONECT   28   29   30   55
CONECT   29   56
CONECT   30   31   57
CONECT   31   58
CONECT   32   33
CONECT   33   34   36   59
CONECT   34   35   60   61
CONECT   35   62
CONECT   36   37   38   63
CONECT   37   64
CONECT   38   39   65
CONECT   39   66
END

HMDB0000290
     RDKit          3D
Uridine diphosphate-N-acetylglucosamine
 66 68  0  0  0  0  0  0  0  0999 V2000
   -6.3921   -4.2518    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3530   -2.7438    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4513   -2.2142    0.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549   -2.0364    0.1332 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0637   -0.6301    0.3085 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6784   -0.1157    0.4589 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2171    0.0381   -0.8804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777   -0.3813   -1.0078 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2482   -0.7684   -2.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -1.6747   -0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541    1.0543   -0.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922    0.9571    0.8006 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.5214    1.5147    1.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4933   -0.7095    1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    1.7160    0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329    0.8400    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4287    0.1818    0.1871 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4179    0.7599   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4357   -0.1854   -0.6056 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7686    0.3633   -0.4829 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7914   -0.4531   -0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0896   -0.0771   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3583    1.1919   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5568    1.5454    0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3008    1.9894    0.2152 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0239    1.5770    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804    2.3260    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3175   -1.0002    0.7149 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0102   -2.1662    0.6626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372   -1.1566    0.7991 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4621   -2.2485   -0.0165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    1.1814    0.9716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3503    2.0236    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5056    3.4039    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    3.8826    0.9203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6905    1.5813   -0.4079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0255    2.4149   -1.4888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6315    0.1400   -0.9197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8550   -0.3554   -1.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4177   -4.5770   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2207   -4.4864   -0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5474   -4.7211    1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3007   -2.5633   -0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353   -0.3168    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -0.7306    1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9121   -2.3484   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -1.1230    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734    0.3317    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916    1.6540    1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611   -0.1335   -0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -0.8796   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5718   -1.4210   -1.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9367   -0.7146   -0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4967    2.9506    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197   -0.3108    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7990   -2.6940    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945   -1.2473    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7323   -1.9741   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6639    2.1016   -0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9690    4.0707   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1200    3.3717    1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2275    4.8555    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4375    1.5932    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9233    2.7481   -1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8664    0.0880   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7288   -1.0379   -1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 19 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  6 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38  5  1  0
 30 17  1  0
 26 20  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  5 44  1  1
  6 45  1  1
 10 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  6
 19 51  1  6
 21 52  1  0
 22 53  1  0
 25 54  1  0
 28 55  1  1
 29 56  1  0
 30 57  1  1
 31 58  1  0
 33 59  1  6
 34 60  1  0
 34 61  1  0
 35 62  1  0
 36 63  1  1
 37 64  1  0
 38 65  1  6
 39 66  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)	ChEBI
UDP-GlcNAc	ChEBI
UDP-N-Acetyl-D-glucosamine	ChEBI
UDP-N-Acetylglucosamine	ChEBI
URIDINE-diphosphATE-N-acetylglucosamine	ChEBI
(2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name)	Generator
URIDINE-diphosphoric acid-N-acetylglucosamine	Generator
Uridine diphosphoric acid-N-acetylglucosamine	Generator
N-[2-[[[5-[(2,4-Dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide	HMDB
UDP-a-D-N-Acetylglucosamine	HMDB
UDP-Acetyl-D-glucosamine	HMDB
UDP-Acetyl-delta-glucosamine	HMDB
UDP-Acetylglucosamine	HMDB
UDP-alpha-D-N-Acetylglucosamine	HMDB
UDP-alpha-delta-N-Acetylglucosamine	HMDB
UDP-N-Acetyl-delta-glucosamine	HMDB
UDP-N-Acetyl-glucosamine	HMDB
UPPAG	HMDB
Uridine 5'-diphospho-N-acetlyglucosamine	HMDB
Uridine 5'-diphospho-N-acetylglucosamine	HMDB
Uridine diphosphate N-acetyl-D-glucosamine	HMDB
Uridine diphosphate N-acetyl-delta-glucosamine	HMDB
Uridine diphosphate N-acetylglucosamine	HMDB
Uridine diphospho-2-acetamido-2-deoxy-D-glucose	HMDB
Uridine diphospho-2-acetamido-2-deoxy-delta-glucose	HMDB
Uridine diphospho-N-acetyl-D-glucosamine	HMDB
Uridine diphospho-N-acetyl-delta-glucosamine	HMDB
Uridine diphospho-N-acetylglucosamine	HMDB
Uridine diphosphoacetylglucosamine	HMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester	HMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester	HMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester	HMDB
Uridine pyrophosphoacetylglucosamine	HMDB
[[3-Acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate	HMDB
[[3-Acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid	HMDB
Acetylglucosamine, UDP	HMDB
Diphosphate N-acetylglucosamine, uridine	HMDB
Diphospho-N-acetylglucosamine, uridine	HMDB
N-Acetylglucosamine, uridine diphosphate	HMDB
Pyrophosphoacetylglucosamine, uridine	HMDB
UDP Acetylglucosamine	HMDB
UDPGNAc	HMDB
Uridine diphosphate N acetylglucosamine	HMDB
Uridine diphospho N acetylglucosamine	HMDB
UDP N-Acetyl-alpha-D-glucosamine	HMDB
UDP N-Acetyl-α-D-glucosamine	HMDB
UDP-Α-D-N-acetylglucosamine	HMDB
Uridine 5'-(2-acetamido-2-deoxy-alpha-D-glucosyl pyrophosphate)	HMDB
Uridine 5'-(2-acetamido-2-deoxy-α-D-glucosyl pyrophosphate)	HMDB
Uridine 5’-(2-acetamido-2-deoxy-α-D-glucosyl pyrophosphate)	HMDB

Chemical Formula

C₁₇H₂₇N₃O₁₇P₂

Average Mass

607.3537 Da

Monoisotopic Mass

607.08157 Da

IUPAC Name

[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional Name

udp-N-acetyl-α-D-glucosamine

CAS Registry Number

528-04-1

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O

InChI Identifier

InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1

InChI Key

LFTYTUAZOPRMMI-CFRASDGPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	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, 252 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, 50 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, 75 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, 101 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	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, 176 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, 201 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
Daphnia pulex	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Escherichia coli	Bacteria	KNApSAcK
Gallus gallus	FooDB	FooDB
Helianthus tuberosus	LOTUS Database	35616633
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 pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
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
Acetamide
Tetrahydrofuran
Heteroaromatic compound
Urea
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Alcohol
Primary alcohol
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-amino sugar (CHEBI:16264 )

Physical Properties

State

Solid

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
Water Solubility	11.4 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	300.41 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	117.56 m³·mol⁻¹	ChemAxon
Polarizability	50.39 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

HMDB0000290

DrugBank ID

DB03397

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

UDP-N-ACETYL-D-GLUCOSAMINE

BiGG ID

33638

Wikipedia Link

Not Available

METLIN ID

5281

PubChem Compound

445675

PDB ID

Not Available

ChEBI ID

16264

Good Scents ID

Not Available

References

General References

Kobayashi T, Sleeman JE, Coughtrie MW, Burchell B: Molecular and functional characterization of microsomal UDP-glucuronic acid uptake by members of the nucleotide sugar transporter (NST) family. Biochem J. 2006 Dec 1;400(2):281-9. [PubMed:16965264 ]
Kim CH: Increased expression of N-acetylglucosaminyltransferase-V in human hepatoma cells by retinoic acid and 1alpha,25-dihydroxyvitamin D3. Int J Biochem Cell Biol. 2004 Nov;36(11):2307-19. [PubMed:15313475 ]
Jamieson JC, Kaplan HA, Woloski BM, Hellman M, Ham K: Glycoprotein biosynthesis during the acute-phase response to inflammation. Can J Biochem Cell Biol. 1983 Sep;61(9):1041-8. [PubMed:6627106 ]
Love DC, Hanover JA: The hexosamine signaling pathway: deciphering the "O-GlcNAc code". Sci STKE. 2005 Nov 29;2005(312):re13. [PubMed:16317114 ]
Wells L, Vosseller K, Hart GW: A role for N-acetylglucosamine as a nutrient sensor and mediator of insulin resistance. Cell Mol Life Sci. 2003 Feb;60(2):222-8. [PubMed:12678487 ]

Showing NP-Card for Uridine diphosphate-N-acetylglucosamine (NP0000283)

MOL for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

3D MOL for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

3D SDF for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

3D-SDF for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

PDB for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

3D PDB for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

SMILES for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

INCHI for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

Structure for NP0000283 (Uridine diphosphate-N-acetylglucosamine)

3D Structure for NP0000283 (Uridine diphosphate-N-acetylglucosamine)