NP-MRD: Showing NP-Card for n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid (NP0315982)

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Record Information

Version

2.0

Created at

2022-09-11 14:52:59 UTC

Updated at

2022-09-11 14:52:59 UTC

NP-MRD ID

NP0315982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid

Description

Tetrahydro-limipterin belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid is found in Chlorobium limicola. Based on a literature review very few articles have been published on Tetrahydro-limipterin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112216532D          

 31 33  0  0  1  0            999 V2000
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 15 22  2  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    9.0373    1.4514    0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5098    0.5755    0.1019 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2550    0.4904    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6339    1.5732    0.9127 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264    1.5378    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422    2.6171    1.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6210    0.3704    0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7080    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086   -0.6416    0.1510 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5323   -1.8775    0.2370 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112   -1.8360   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3783   -0.7568    0.6825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4043   -0.0599   -0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9772    0.6318   -1.2554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -0.9420   -0.5785 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5601   -1.9203   -1.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7776   -0.1298   -1.1061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8860   -0.3415   -0.3272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9541   -0.8971   -1.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -1.3757   -0.1311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9396   -2.1959   -0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8285   -2.6551    0.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4858   -0.2833    0.6881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3015    0.4843   -0.1146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4303    0.6059    1.2934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7145   -0.0932    2.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285    0.9806    0.2191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0622    1.6495   -0.8962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    2.8816   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1344    3.8550    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9744    3.3765   -2.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    0.2270    1.2837 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1576    3.2488    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.5015   -0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0065   -2.7974    0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7039   -2.8386    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -1.7155   -1.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7707   -1.1885    1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297    0.7401    0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    1.0187   -1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0961   -1.5089    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569   -2.8756   -1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -1.4890   -2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4332   -2.2182   -2.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055   -1.0727    0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2895   -2.0882    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5141   -1.6448   -1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069   -3.1016   -1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6343   -3.6149    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1179   -0.7651    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480    0.3065   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8772    1.4768    1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617   -1.0326    2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958    1.5470    0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712    3.9703    0.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9159    4.8823   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2691    3.5888    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9589    3.2063   -2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8255    0.8731    1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  7  2  0
  7 32  1  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  3  9  1  0
 27 18  1  0
 32 12  1  0
  9  8  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 15 41  1  1
 18 45  1  1
 20 46  1  1
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  1
 24 51  1  0
 25 52  1  1
 26 53  1  0
 27 54  1  1
 30 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 13 39  1  1
 14 40  1  0
 12 38  1  1
 11 36  1  0
 11 37  1  0
 10 35  1  0
 32 59  1  0
  6 33  1  0
  2  1  1  0
  9 34  1  0
M  END


  Mrv1652309112216532D          

 31 33  0  0  1  0            999 V2000
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 15 22  2  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](OC1OC(CO)C(O)C(O)C1N=C(C)O)[C@H](O)C1CNC2=C(N1)C(O)=NC(=N)N2

> <INCHI_IDENTIFIER>
InChI=1S/C17H28N6O8/c1-5(11(26)7-3-19-14-10(21-7)15(29)23-17(18)22-14)30-16-9(20-6(2)25)13(28)12(27)8(4-24)31-16/h5,7-9,11-13,16,21,24,26-28H,3-4H2,1-2H3,(H,20,25)(H4,18,19,22,23,29)/t5-,7?,8?,9?,11-,12?,13?,16?/m0/s1

> <INCHI_KEY>
QWYAJQBOCWNVLL-GMQDJYRHSA-N

> <FORMULA>
C17H28N6O8

> <MOLECULAR_WEIGHT>
444.445

> <EXACT_MASS>
444.196861886

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.194681888910345

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(4,5-dihydroxy-2-{[(1R,2S)-1-hydroxy-1-(4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid

> <JCHEM_LOGP>
-3.718915793127078

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
7.534202222153539

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.3969609920696815

> <JCHEM_PKA_STRONGEST_BASIC>
6.0213240314501695

> <JCHEM_POLAR_SURFACE_AREA>
224.49999999999994

> <JCHEM_REFRACTIVITY>
123.4842

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-(4,5-dihydroxy-2-{[(1R,2S)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -4.001  -6.930   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       8.002  -0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   12                                                       
CONECT   24    6   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    5   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₈N₆O₈

Average Mass

444.4450 Da

Monoisotopic Mass

444.19686 Da

IUPAC Name

N-(4,5-dihydroxy-2-{[(1R,2S)-1-hydroxy-1-(4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid

Traditional Name

N-(4,5-dihydroxy-2-{[(1R,2S)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid

CAS Registry Number

Not Available

SMILES

C[C@H](OC1OC(CO)C(O)C(O)C1N=C(C)O)[C@H](O)C1CNC2=C(N1)C(O)=NC(=N)N2

InChI Identifier

InChI=1S/C17H28N6O8/c1-5(11(26)7-3-19-14-10(21-7)15(29)23-17(18)22-14)30-16-9(20-6(2)25)13(28)12(27)8(4-24)31-16/h5,7-9,11-13,16,21,24,26-28H,3-4H2,1-2H3,(H,20,25)(H4,18,19,22,23,29)/t5-,7?,8?,9?,11-,12?,13?,16?/m0/s1

InChI Key

QWYAJQBOCWNVLL-GMQDJYRHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Chlorobium limicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
N-acyl-alpha-hexosamine
Glycosyl compound
O-glycosyl compound
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monosaccharide
Oxane
Imidolactam
Pyrimidine
Heteroaromatic compound
Acetamide
Vinylogous amide
1,2-aminoalcohol
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Secondary amine
Acetal
Oxacycle
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Primary amine
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

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
logP	-3.7	ChemAxon
pKa (Strongest Acidic)	5.4	ChemAxon
pKa (Strongest Basic)	6.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	224.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.48 m³·mol⁻¹	ChemAxon
Polarizability	43.19 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78445523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid (NP0315982)

MOL for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

3D MOL for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

3D SDF for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

3D-SDF for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

PDB for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

3D PDB for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

SMILES for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

INCHI for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

Structure for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)

3D Structure for NP0315982 (n-(4,5-dihydroxy-2-{[(1r,2s)-1-hydroxy-1-(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl)propan-2-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid)