Showing metabocard for GDP-alpha-D-rhamnose (MMDBc0056008)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 20:13:07 UTC
Update Date2025-10-07 16:09:30 UTC
Metabolite IDMMDBc0056008
Metabolite Identification
Common NameGDP-alpha-D-rhamnose
DescriptionGDP-alpha-D-rhamnose is a nucleotide sugar belonging to the class of glycosyl donors. Its chemical structure features a guanosine diphosphate (GDP) moiety linked to the sugar alpha-D-rhamnose, which is a 6-deoxy sugar. The identification of GDP-alpha-D-rhamnose was achieved through nuclear magnetic resonance spectroscopy, confirming its role as a product in specific biosynthetic pathways (PMID:11096116 ). This metabolite is involved in the biosynthesis of polysaccharides and glycoproteins, where it acts as a substrate for glycosyltransferases, facilitating the addition of rhamnose residues to growing carbohydrate chains. Additionally, GDP-alpha-D-rhamnose, along with other GDP-sugars like GDP-alpha-D-mannose and GDP-alpha-D-glucose, has been shown to exhibit strong inhibitory effects on certain enzymatic activities, indicating its potential regulatory roles in carbohydrate metabolism (PMID:213433 ). Overall, GDP-alpha-D-rhamnose serves as a critical component in the synthesis of complex carbohydrates, contributing to various cellular functions.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fadc8aaf550>


  Mrv1652306172222132D          

 47 50  0  0  1  0            999 V2000
   -5.7689   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152   -7.7804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -8.6009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1753   -8.9365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5079   -8.4516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5941   -7.6311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5964   -9.0858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -9.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542   -8.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.9166   -4.3528    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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   -2.1924   -6.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -4.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -7.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267   -7.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -5.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -5.0203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2616   -8.1160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -2.0824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -9.2720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8404   -7.9666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  1  0  0  0
  5  2  1  1  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
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 13  6  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18  3  2  0  0  0  0
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 19 12  1  0  0  0  0
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 20 16  1  0  0  0  0
 21  3  1  0  0  0  0
 21 12  1  0  0  0  0
 14 21  1  1  0  0  0
  7 22  1  6  0  0  0
  8 23  1  6  0  0  0
  9 24  1  6  0  0  0
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 11 26  1  1  0  0  0
 27 13  1  0  0  0  0
 32  2  1  0  0  0  0
 33  4  1  0  0  0  0
 33 15  1  0  0  0  0
 34  5  1  0  0  0  0
 34 14  1  0  0  0  0
 15 35  1  6  0  0  0
 37 28  1  0  0  0  0
 37 29  2  0  0  0  0
 37 32  1  0  0  0  0
 37 36  1  0  0  0  0
 38 30  1  0  0  0  0
 38 31  2  0  0  0  0
 38 35  1  0  0  0  0
 38 36  1  0  0  0  0
  4 39  1  6  0  0  0
  5 40  1  6  0  0  0
  7 41  1  1  0  0  0
  8 42  1  1  0  0  0
  9 43  1  6  0  0  0
 10 44  1  1  0  0  0
 11 45  1  6  0  0  0
 14 46  1  6  0  0  0
 15 47  1  1  0  0  0
M  CHG  2  27  -1  28  -1
M  END
Download

3D MOL for #<Metabolite:0x00007fadc8aaf550>

Download
3D SDF for #<Metabolite:0x00007fadc8aaf550>

  Mrv1652306172222132D          

 47 50  0  0  1  0            999 V2000
   -5.7689   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152   -7.7804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -8.6009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1753   -8.9365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5079   -8.4516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5941   -7.6311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5964   -9.0858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -9.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542   -8.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.9166   -4.3528    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.9468   -5.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -6.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924   -6.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -4.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -7.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267   -7.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -5.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -5.0203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129   -6.3257    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827   -8.2654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0540   -4.0448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428   -9.4214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -3.6139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616   -8.1160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -2.0824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -9.2720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -1.5666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8404   -7.9666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  1  0  0  0
  5  2  1  1  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  2  0  0  0  0
 13  6  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18  3  2  0  0  0  0
 18  6  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 13  2  0  0  0  0
 20 16  1  0  0  0  0
 21  3  1  0  0  0  0
 21 12  1  0  0  0  0
 14 21  1  1  0  0  0
  7 22  1  6  0  0  0
  8 23  1  6  0  0  0
  9 24  1  6  0  0  0
 10 25  1  6  0  0  0
 11 26  1  1  0  0  0
 27 13  1  0  0  0  0
 32  2  1  0  0  0  0
 33  4  1  0  0  0  0
 33 15  1  0  0  0  0
 34  5  1  0  0  0  0
 34 14  1  0  0  0  0
 15 35  1  6  0  0  0
 37 28  1  0  0  0  0
 37 29  2  0  0  0  0
 37 32  1  0  0  0  0
 37 36  1  0  0  0  0
 38 30  1  0  0  0  0
 38 31  2  0  0  0  0
 38 35  1  0  0  0  0
 38 36  1  0  0  0  0
  4 39  1  6  0  0  0
  5 40  1  6  0  0  0
  7 41  1  1  0  0  0
  8 42  1  1  0  0  0
  9 43  1  6  0  0  0
 10 44  1  1  0  0  0
 11 45  1  6  0  0  0
 14 46  1  6  0  0  0
 15 47  1  1  0  0  0
M  CHG  2  27  -1  28  -1
M  END
> <DATABASE_ID>
MMDBc0056008

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C)[C@@]([H])(O)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1

> <INCHI_KEY>
LQEBEXMHBLQMDB-GDJBGNAASA-L

> <FORMULA>
C16H23N5O15P2

> <MOLECULAR_WEIGHT>
587.329

> <EXACT_MASS>
587.067686216

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.12801651919347

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl phosphono]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate

> <JCHEM_LOGP>
-4.7463169002200365

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.7816533430109756

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7078968338117804

> <JCHEM_PKA_STRONGEST_BASIC>
3.3839265821482374

> <JCHEM_POLAR_SURFACE_AREA>
313.8500000000001

> <JCHEM_REFRACTIVITY>
136.97729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy([(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl phosphono]oxy}methyl)oxolan-2-yl]-2-imino-3H-purin-6-olate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fadc8aaf550>
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PDB for #<Metabolite:0x00007fadc8aaf550>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0     -10.769 -13.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.454  -6.934   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.362 -14.523   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.208  -6.029   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.201 -16.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.744  -6.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.794 -16.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.161  -5.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.548 -15.776   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.709 -14.245   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.198  -2.843   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0     -10.447 -16.960   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.268  -7.970   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.633 -18.213   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.701  -5.259   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.141 -16.403   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      -5.444  -8.125   0.000  0.00  0.00           O-1
HETATM   29  O   UNK     0      -3.634 -10.617   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -7.156 -11.969   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.093 -11.647   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.293  -8.466   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -8.116 -13.618   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.208  -4.489   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.463 -13.339   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -5.785 -10.276   0.000  0.00  0.00           O+0
HETATM   37  P   UNK     0      -4.539  -9.371   0.000  0.00  0.00           P+0
HETATM   38  P   UNK     0      -5.624 -11.808   0.000  0.00  0.00           P+0
HETATM   39  H   UNK     0     -10.608 -15.429   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.967  -7.550   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      -9.040 -17.587   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.777  -6.746   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -7.955 -15.150   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.861  -3.887   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.387 -17.308   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.833  -2.924   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.302 -14.871   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5   32                                                       
CONECT    3   18   21                                                       
CONECT    4    1    7   33   39                                             
CONECT    5    2    8   34   40                                             
CONECT    6   12   13   18                                                  
CONECT    7    4    9   22   41                                             
CONECT    8    5   10   23   42                                             
CONECT    9    7   11   24   43                                             
CONECT   10    8   14   25   44                                             
CONECT   11    9   15   26   45                                             
CONECT   12    6   19   21                                                  
CONECT   13    6   20   27                                                  
CONECT   14   10   21   34   46                                             
CONECT   15   11   33   35   47                                             
CONECT   16   17   19   20                                                  
CONECT   17   16                                                            
CONECT   18    3    6                                                       
CONECT   19   12   16                                                       
CONECT   20   13   16                                                       
CONECT   21    3   12   14                                                  
CONECT   22    7                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   13                                                            
CONECT   28   37                                                            
CONECT   29   37                                                            
CONECT   30   38                                                            
CONECT   31   38                                                            
CONECT   32    2   37                                                       
CONECT   33    4   15                                                       
CONECT   34    5   14                                                       
CONECT   35   15   38                                                       
CONECT   36   37   38                                                       
CONECT   37   28   29   32   36                                             
CONECT   38   30   31   35   36                                             
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

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3D PDB for #<Metabolite:0x00007fadc8aaf550>
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SMILES for #<Metabolite:0x00007fadc8aaf550>
[H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C)[C@@]([H])(O)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O
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INCHI for #<Metabolite:0x00007fadc8aaf550>
InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1
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Synonyms
ValueSource
GDP-6-Deoxy-alpha-D-mannose dianionChEBI
GDP-alpha-D-RhamnoseChEBI
GDP-6-Deoxy-a-D-mannose dianionGenerator
GDP-6-Deoxy-α-D-mannose dianionGenerator
GDP-a-D-RhamnoseGenerator
GDP-Α-D-rhamnoseGenerator
GDP-6-Deoxy-a-D-mannose(2-)Generator
GDP-6-Deoxy-α-D-mannose(2-)Generator
Molecular FormulaC16H23N5O15P2
Average Mass587.329
Monoisotopic Mass587.067686216
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl phosphono]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate
Traditional Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy([(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl phosphono]oxy}methyl)oxolan-2-yl]-2-imino-3H-purin-6-olate
CAS Registry NumberNot Available
SMILES
[H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C)[C@@]([H])(O)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O
InChI Identifier
InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1
InChI KeyLQEBEXMHBLQMDB-GDJBGNAASA-L