NP-MRD: Showing NP-Card for (2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid (NP0169831)

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Record Information

Version

2.0

Created at

2022-09-03 05:51:13 UTC

Updated at

2022-09-03 05:51:13 UTC

NP-MRD ID

NP0169831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid

Description

N10-Formyl-THF, also known as 10-formyl-THF or 10-FTHF, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. N10-Formyl-THF is a strong basic compound (based on its pKa). N10-Formyl-THF exists in both E. (2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid is found in Trypanosoma brucei. Coli (prokaryote) and yeast (eukaryote).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241222232D          

 34 36  0  0  1  0            999 V2000
   -0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5736    2.0627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 30  1  2  0  0  0  0
 30  6  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3 28  1  0  0  0  0
  4  8  1  0  0  0  0
  7  5  1  0  0  0  0
 28  6  1  0  0  0  0
  8  9  1  1  0  0  0
  9 32  1  0  0  0  0
 32 10  1  0  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 16 17  2  0  0  0  0
 20 18  1  1  0  0  0
 26 19  2  0  0  0  0
 20 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  2  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
  7  8  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 32 34  1  0  0  0  0
 34 33  2  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -8.7727   -1.5457    2.2326 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6248   -1.1077    1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9002   -0.0479    1.8878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8356    0.4122    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128   -0.2217    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1632   -1.3160   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7835   -1.8966   -1.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2446   -1.7447    0.3633 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2803    0.2056   -0.6565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905    1.1587   -0.0651 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5030    1.8862   -1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    1.0426   -1.7701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.5315   -3.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749   -0.2114   -3.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421    0.7142   -1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391    1.7784   -1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    1.5636   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2450    0.2789   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    0.0651    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1923    1.0654    0.6672 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056   -1.1945    0.1107 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936   -1.6394    0.5120 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4639   -0.4553    0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6064    0.1444   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5105    1.3125   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256    2.4154   -0.2604 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8373    1.2272   -1.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5331   -2.4892    1.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795   -2.7858    2.3090 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319   -2.9781    2.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3682   -0.7557   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672   -0.5484   -0.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504    2.2007    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0670    1.5323    1.6740 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7353   -1.2854    2.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5523   -2.1723    3.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7758   -2.5584    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1678   -0.2108   -1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806    0.6839    0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746    2.5799   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1045    2.5739   -1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0082    0.7377   -3.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2448    2.8019   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5378    2.3574   -0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683   -1.9616   -0.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9033   -2.2712   -0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4535   -0.9246    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1512    0.2933    1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6687    0.3455   -1.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2002   -0.6225   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4557    0.5244   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2133   -3.7858    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -1.7665   -0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -1.3808   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6139    2.9868    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8975    2.6402   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1193    1.8180    2.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
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 16 17  1  0
 17 18  2  0
 18 31  1  0
 31 32  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 27  1  0
 25 26  2  0
 22 28  1  0
 28 30  1  0
 28 29  2  0
 10 33  1  0
 33 34  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  2  1  0
 34  4  1  0
 32 15  1  0
  1 35  1  0
  1 36  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  0
 11 41  1  0
 13 42  1  0
 16 43  1  0
 17 44  1  0
 31 53  1  0
 32 54  1  0
 21 45  1  0
 22 46  1  6
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 27 51  1  0
 30 52  1  0
 33 55  1  0
 33 56  1  0
 34 57  1  0
  8 37  1  0
M  END


  Mrv0541 02241222232D          

 34 36  0  0  1  0            999 V2000
   -0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5736    2.0627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 30  1  2  0  0  0  0
 30  6  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3 28  1  0  0  0  0
  4  8  1  0  0  0  0
  7  5  1  0  0  0  0
 28  6  1  0  0  0  0
  8  9  1  1  0  0  0
  9 32  1  0  0  0  0
 32 10  1  0  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 16 17  2  0  0  0  0
 20 18  1  1  0  0  0
 26 19  2  0  0  0  0
 20 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  2  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
  7  8  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 32 34  1  0  0  0  0
 34 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0169831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC2=C(N[C@@H](CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11-,13+/m1/s1

> <INCHI_KEY>
AUFGTPPARQZWDO-YPMHNXCESA-N

> <FORMULA>
C20H23N7O7

> <MOLECULAR_WEIGHT>
473.4393

> <EXACT_MASS>
473.165896125

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
46.63277487497841

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[4-(N-{[(6R)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid

> <ALOGPS_LOGP>
-1.79

> <JCHEM_LOGP>
-3.371732827151703

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.597415477616566

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8185105858286112

> <JCHEM_PKA_STRONGEST_BASIC>
4.472180456626537

> <JCHEM_POLAR_SURFACE_AREA>
215.55

> <JCHEM_REFRACTIVITY>
124.88119999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-formyltetrahydrofolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.334  -1.540   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334   1.540   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       1.334  -1.540   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      -2.667   0.770   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669   5.390   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      12.003   3.080   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      13.337   8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.337   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.004   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.670   3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.337   5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.671   6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.671   7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.004   8.470   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334   3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -4.001  -1.540   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       5.335   0.770   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       4.001  -1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
CONECT    1   30    2                                                       
CONECT    2    1    3    5                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    8                                                       
CONECT    5    2    7                                                       
CONECT    6   30   28                                                       
CONECT    7    5    8                                                       
CONECT    8    4    9    7                                                  
CONECT    9    8   32                                                       
CONECT   10   32   12   13                                                  
CONECT   11   12   15                                                       
CONECT   12   10   11                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   11   14   16                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   20                                                       
CONECT   19   26                                                            
CONECT   20   18   24   22                                                  
CONECT   21   22                                                            
CONECT   22   20   21   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   19   25   27                                                  
CONECT   27   26                                                            
CONECT   28    3    6   29                                                  
CONECT   29   28                                                            
CONECT   30    1    6   31                                                  
CONECT   31   30                                                            
CONECT   32    9   10   34                                                  
CONECT   33   34                                                            
CONECT   34   32   33                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(6S)-10-HCO-H4Folate	ChEBI
10-Formyl-THF	ChEBI
10-Formyltetrahydrofolate	ChEBI
10-Formyltetrahydropteroylglutamic acid	ChEBI
10-FTHF	ChEBI
N-(10-Formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid	ChEBI
(6S)-10-HCO-H4Folic acid	Generator
10-Formyltetrahydrofolic acid	Generator
10-Formyltetrahydropteroylglutamate	Generator
N-(10-Formyl-5,6,7,8-tetrahydropteroyl)-L-glutamate	Generator

Chemical Formula

C₂₀H₂₃N₇O₇

Average Mass

473.4393 Da

Monoisotopic Mass

473.16590 Da

IUPAC Name

(2S)-2-{[4-(N-{[(6R)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid

Traditional Name

10-formyltetrahydrofolic acid

CAS Registry Number

Not Available

SMILES

NC1=NC2=C(N[C@@H](CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1

InChI Identifier

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11-,13+/m1/s1

InChI Key

AUFGTPPARQZWDO-YPMHNXCESA-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
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Tetrahydrofolic acids

Alternative Parents

Substituents

Tetrahydrofolic acid
Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
Acylaminobenzoic acid or derivatives
Alpha-amino acid or derivatives
Anilide
Benzoic acid or derivatives
Benzamide
Benzoyl
Pyrimidone
Aminopyrimidine
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Carboxylic acid derivative
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

formyltetrahydrofolic acid (CHEBI:15637 )

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	-1.8	ALOGPS
logP	-3.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.82	ChemAxon
pKa (Strongest Basic)	4.47	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	215.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.88 m³·mol⁻¹	ChemAxon
Polarizability	46.63 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

C00007251

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6326742

PDB ID

Not Available

ChEBI ID

15637

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid (NP0169831)

MOL for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

3D MOL for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

3D SDF for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

3D-SDF for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

PDB for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

3D PDB for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

SMILES for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

INCHI for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

Structure for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)

3D Structure for NP0169831 ((2s)-2-{[4-(n-{[(6r)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1h-pteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid)