MiMeDB: Showing metabocard for (6S)-NADPHX (MMDBc0054981)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:06 UTC

Update Date

2022-08-12 20:09:10 UTC

Metabolite ID

MMDBc0054981

Metabolite Identification

Common Name

(6S)-NADPHX

Description

(S)-NADPHX(4-), also known as (6S)-nadphx, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Based on a literature review very few articles have been published on (S)-NADPHX(4-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 58 62  0  0  1  0            999 V2000
   -9.3338   -1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7817   -2.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2719   -1.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0788   -1.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5853   -1.6065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9748   -2.4231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7568   -0.7995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5773   -0.7133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6309   -0.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9129   -1.4670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4378   -0.7554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7198   -1.6385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4227   -3.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048   -0.1865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9898    0.0012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3759    0.2008    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.8917   -1.7235    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.3207   -0.8985    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.0187   -2.0255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2998   -2.0190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -2.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062   -1.3110    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9442   -1.0873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -1.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2297   -3.2078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525   -0.0293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986   -1.3931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4012   -0.7565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432    0.1385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1264   -2.2639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3004    0.6542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  8  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  1  1  0  0  0
 10  5  1  1  0  0  0
 11  2  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 12  2  0  0  0  0
 18  8  1  0  0  0  0
 19 12  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24  6  2  0  0  0  0
 24 17  1  0  0  0  0
 25  6  1  0  0  0  0
 25 19  2  0  0  0  0
 26  7  2  0  0  0  0
 26 12  1  0  0  0  0
 27  3  1  0  0  0  0
 27 11  1  0  0  0  0
 20 27  1  1  0  0  0
 28  7  1  0  0  0  0
 28 19  1  0  0  0  0
 21 28  1  1  0  0  0
 11 29  1  1  0  0  0
 13 30  1  6  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 33 18  1  0  0  0  0
 41  4  1  0  0  0  0
 42  5  1  0  0  0  0
 43  9  1  0  0  0  0
 43 20  1  0  0  0  0
 44 10  1  0  0  0  0
 44 21  1  0  0  0  0
 16 45  1  6  0  0  0
 47 34  1  0  0  0  0
 47 35  1  0  0  0  0
 47 36  2  0  0  0  0
 47 45  1  0  0  0  0
 48 37  1  0  0  0  0
 48 38  2  0  0  0  0
 48 41  1  0  0  0  0
 48 46  1  0  0  0  0
 49 39  1  0  0  0  0
 49 40  2  0  0  0  0
 49 42  1  0  0  0  0
 49 46  1  0  0  0  0
  9 50  1  6  0  0  0
 10 51  1  6  0  0  0
 11 52  1  6  0  0  0
 13 53  1  1  0  0  0
 14 54  1  1  0  0  0
 15 55  1  1  0  0  0
 16 56  1  1  0  0  0
 20 57  1  6  0  0  0
 21 58  1  6  0  0  0
M  CHG  4  33  -1  34  -1  35  -1  37  -1
M  END


  Mrv1652306172221392D          

 58 62  0  0  1  0            999 V2000
   -9.3338   -1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7817   -2.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2719   -1.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0788   -1.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5853   -1.6065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9748   -2.4231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7568   -0.7995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5773   -0.7133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6309   -0.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9129   -1.4670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4378   -0.7554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7198   -1.6385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4227   -3.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048   -0.1865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9898    0.0012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3759    0.2008    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.8917   -1.7235    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.3207   -0.8985    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.0187   -2.0255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2998   -2.0190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -2.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062   -1.3110    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9442   -1.0873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -1.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2297   -3.2078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525   -0.0293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986   -1.3931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4012   -0.7565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432    0.1385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1264   -2.2639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3004    0.6542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  8  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  1  1  0  0  0
 10  5  1  1  0  0  0
 11  2  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 12  2  0  0  0  0
 18  8  1  0  0  0  0
 19 12  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24  6  2  0  0  0  0
 24 17  1  0  0  0  0
 25  6  1  0  0  0  0
 25 19  2  0  0  0  0
 26  7  2  0  0  0  0
 26 12  1  0  0  0  0
 27  3  1  0  0  0  0
 27 11  1  0  0  0  0
 20 27  1  1  0  0  0
 28  7  1  0  0  0  0
 28 19  1  0  0  0  0
 21 28  1  1  0  0  0
 11 29  1  1  0  0  0
 13 30  1  6  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 33 18  1  0  0  0  0
 41  4  1  0  0  0  0
 42  5  1  0  0  0  0
 43  9  1  0  0  0  0
 43 20  1  0  0  0  0
 44 10  1  0  0  0  0
 44 21  1  0  0  0  0
 16 45  1  6  0  0  0
 47 34  1  0  0  0  0
 47 35  1  0  0  0  0
 47 36  2  0  0  0  0
 47 45  1  0  0  0  0
 48 37  1  0  0  0  0
 48 38  2  0  0  0  0
 48 41  1  0  0  0  0
 48 46  1  0  0  0  0
 49 39  1  0  0  0  0
 49 40  2  0  0  0  0
 49 42  1  0  0  0  0
 49 46  1  0  0  0  0
  9 50  1  6  0  0  0
 10 51  1  6  0  0  0
 11 52  1  6  0  0  0
 13 53  1  1  0  0  0
 14 54  1  1  0  0  0
 15 55  1  1  0  0  0
 16 56  1  1  0  0  0
 20 57  1  6  0  0  0
 21 58  1  6  0  0  0
M  CHG  4  33  -1  34  -1  35  -1  37  -1
M  END
> <DATABASE_ID>
MMDBc0054981

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP(O)(=O)OP([O-])(=O)OC[C@@]2([H])O[C@@]([H])(N3C=C(CC[C@]3([H])O)C([O-])=N)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(OP([O-])([O-])=O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32N7O18P3/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(45-47(34,35)36)14(31)10(44-21)5-42-49(39,40)46-48(37,38)41-4-9-13(30)15(32)20(43-9)27-3-8(18(23)33)1-2-11(27)29/h3,6-7,9-11,13-16,20-21,29-32H,1-2,4-5H2,(H2,23,33)(H,37,38)(H,39,40)(H2,22,24,25)(H2,34,35,36)/p-4/t9-,10-,11+,13-,14-,15-,16-,20-,21-/m1/s1

> <INCHI_KEY>
SZKXTJUOKARGIY-VPHRTNKSSA-J

> <FORMULA>
C21H28N7O18P3

> <MOLECULAR_WEIGHT>
759.409

> <EXACT_MASS>
759.072562403

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
63.42285154305422

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-1,4,5,6-tetrahydropyridine-3-carboximidate

> <JCHEM_LOGP>
-8.594711310949592

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
0.8841644039228655

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.29528950236053664

> <JCHEM_PKA_STRONGEST_BASIC>
12.091108197591458

> <JCHEM_POLAR_SURFACE_AREA>
396.6900000000001

> <JCHEM_REFRACTIVITY>
173.04160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-5,6-dihydro-4H-pyridine-3-carboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
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HETATM    2  C   UNK     0     -16.393  -4.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.441  -1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.019  -3.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.061  -2.789   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.947  -2.234   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.426  -2.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.185  -1.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.886  -4.523   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.746  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.650  -2.359   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.278  -1.332   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.555  -1.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -17.978  -1.090   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.904  -2.738   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.924   5.923   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0     -19.484  -1.410   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0     -14.410  -3.059   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0     -13.856  -5.668   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -9.716  -0.348   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.126  -3.824   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -13.048   0.002   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -17.502   0.375   0.000  0.00  0.00           O-1
HETATM   34  O   UNK     0       3.531  -3.217   0.000  0.00  0.00           O-1
HETATM   35  O   UNK     0       6.199  -1.677   0.000  0.00  0.00           O-1
HETATM   36  O   UNK     0       5.635  -3.781   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.740  -1.940   0.000  0.00  0.00           O-1
HETATM   38  O   UNK     0      -6.993  -4.753   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -4.619  -1.822   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.808  -4.313   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -7.773  -2.720   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -2.468  -2.162   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -11.760  -3.769   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.185  -0.344   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       4.095  -1.114   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -4.959  -3.973   0.000  0.00  0.00           O+0
HETATM   47  P   UNK     0       4.865  -2.447   0.000  0.00  0.00           P+0
HETATM   48  P   UNK     0      -6.366  -3.346   0.000  0.00  0.00           P+0
HETATM   49  P   UNK     0      -3.714  -3.068   0.000  0.00  0.00           P+0
HETATM   50  H   UNK     0      -9.229  -2.030   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.426  -3.405   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0     -15.362  -5.988   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0     -11.298  -0.055   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.171  -2.600   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0     -13.816  -1.412   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.254   0.259   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0     -13.303  -4.226   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.561   1.221   0.000  0.00  0.00           H+0
CONECT    1    2    8                                                       
CONECT    2    1   11                                                       
CONECT    3    8   27                                                       
CONECT    4    9   41                                                       
CONECT    5   10   42                                                       
CONECT    6   24   25                                                       
CONECT    7   26   28                                                       
CONECT    8    1    3   18                                                  
CONECT    9    4   13   43   50                                             
CONECT   10    5   14   44   51                                             
CONECT   11    2   27   29   52                                             
CONECT   12   17   19   26                                                  
CONECT   13    9   15   30   53                                             
CONECT   14   10   16   31   54                                             
CONECT   15   13   20   32   55                                             
CONECT   16   14   21   45   56                                             
CONECT   17   12   22   24                                                  
CONECT   18    8   23   33                                                  
CONECT   19   12   25   28                                                  
CONECT   20   15   27   43   57                                             
CONECT   21   16   28   44   58                                             
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24    6   17                                                       
CONECT   25    6   19                                                       
CONECT   26    7   12                                                       
CONECT   27    3   11   20                                                  
CONECT   28    7   19   21                                                  
CONECT   29   11                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   18                                                            
CONECT   34   47                                                            
CONECT   35   47                                                            
CONECT   36   47                                                            
CONECT   37   48                                                            
CONECT   38   48                                                            
CONECT   39   49                                                            
CONECT   40   49                                                            
CONECT   41    4   48                                                       
CONECT   42    5   49                                                       
CONECT   43    9   20                                                       
CONECT   44   10   21                                                       
CONECT   45   16   47                                                       
CONECT   46   48   49                                                       
CONECT   47   34   35   36   45                                             
CONECT   48   37   38   41   46                                             
CONECT   49   39   40   42   46                                             
CONECT   50    9                                                            
CONECT   51   10                                                            
CONECT   52   11                                                            
CONECT   53   13                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   20                                                            
CONECT   58   21                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  124    0
END

Synonyms

Value	Source
(6S)-NADPHX	ChEBI

Molecular Formula

C₂₁H₂₈N₇O₁₈P₃

Average Mass

759.409

Monoisotopic Mass

759.072562403

IUPAC Name

(6S)-1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-1,4,5,6-tetrahydropyridine-3-carboximidate

Traditional Name

(6S)-1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-5,6-dihydro-4H-pyridine-3-carboximidate

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(=O)OP([O-])(=O)OC[C@@]2([H])O[C@@]([H])(N3C=C(CC[C@]3([H])O)C([O-])=N)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(OP([O-])([O-])=O)[C@]1([H])O

InChI Identifier

InChI=1S/C21H32N7O18P3/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(45-47(34,35)36)14(31)10(44-21)5-42-49(39,40)46-48(37,38)41-4-9-13(30)15(32)20(43-9)27-3-8(18(23)33)1-2-11(27)29/h3,6-7,9-11,13-16,20-21,29-32H,1-2,4-5H2,(H2,23,33)(H,37,38)(H,39,40)(H2,22,24,25)(H2,34,35,36)/p-4/t9-,10-,11+,13-,14-,15-,16-,20-,21-/m1/s1

InChI Key

SZKXTJUOKARGIY-VPHRTNKSSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside 2',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Nicotinamide-nucleotide
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Tetrahydropyridine
Imidolactam
Alkyl phosphate
Hydropyridine
Pyrimidine
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Vinylogous amide
Azole
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Primary carboxylic acid amide
Carboxamide group
Secondary alcohol
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alkanolamine
Oxacycle
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Primary amine
Organooxygen compound
Amine
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleotide-sugar oxoanion (CHEBI:64076 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-8.6	ChemAxon
pKa (Strongest Acidic)	0.3	ChemAxon
pKa (Strongest Basic)	12.09	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	396.69 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	173.04 m³·mol⁻¹	ChemAxon
Polarizability	63.42 Å³	ChemAxon
Number of Rings	5	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	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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
Bacteria	Aquificae	1
Archaea/Archaea	Euryarchaeota	7
Bacteria	Actinobacteria	7	Human
Bacteria	Proteobacteria	21	Human ; Human feces; Human sputum
Bacteria	Dictyoglomi	1
Bacteria	Cyanobacteria	2
Archaea/Archaea	Crenarchaeota	3
Archaea/Archaea	Korarchaeota	1
Bacteria	Firmicutes	24	Human ; Human feces
Bacteria	Bacteroidetes	2
Bacteria	nah	1
Bacteria	Synergistetes	1
Bacteria	Thermotogae	1
Bacteria	Nitrospirae	1
Eukaryota/Fungi	Ascomycota	12
Archaea/Archaea	Thaumarchaeota	2
Eukaryota/Fungi	Basidiomycota	4
Bacteria	Chloroflexi	1
Bacteria	Elusimicrobia	1
Bacteria	Planctomycetes	5	Human feces
Bacteria	Deinococcus-thermus	1
Eukaryota/Fungi	Chytridiomycota	1

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

27471371

KEGG Compound ID

Not Available

BioCyc ID

CPD0-2474

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56927959

PDB ID

Not Available

ChEBI ID

64076

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 (6S)-NADPHX (MMDBc0054981)

MOL for #<Metabolite:0x00007fecbb9a3e18>

3D MOL for #<Metabolite:0x00007fecbb9a3e18>

3D SDF for #<Metabolite:0x00007fecbb9a3e18>

3D-SDF for #<Metabolite:0x00007fecbb9a3e18>

PDB for #<Metabolite:0x00007fecbb9a3e18>

3D PDB for #<Metabolite:0x00007fecbb9a3e18>

SMILES for #<Metabolite:0x00007fecbb9a3e18>

INCHI for #<Metabolite:0x00007fecbb9a3e18>

Structure for #<Metabolite:0x00007fecbb9a3e18>

3D Structure for #<Metabolite:0x00007fecbb9a3e18>