NP-MRD: Showing NP-Card for (2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid (NP0153165)

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Record Information

Version

2.0

Created at

2022-09-02 09:46:06 UTC

Updated at

2022-09-02 09:46:06 UTC

NP-MRD ID

NP0153165

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

Description

Modufolin 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. Modufolin is a strong basic compound (based on its pKa). Modufolin exists in both E. Coli (prokaryote) and yeast (eukaryote).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241222382D          

 34 37  0  0  1  0            999 V2000
    4.2868    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0626    0.0000 C   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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4304    4.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7159    4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303    3.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1446    2.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1448    4.9498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -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
   -1.4292   -1.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8582   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291    0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  1  2  0  0  0  0
  8  1  1  0  0  0  0
  5  3  2  0  0  0  0
  3  8  1  0  0  0  0
  6  4  1  0  0  0  0
  4  8  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
 21  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 16  9  1  0  0  0  0
 15 10  1  0  0  0  0
 13 10  2  0  0  0  0
 18 10  1  0  0  0  0
 14 12  1  0  0  0  0
 12 17  1  1  0  0  0
 15 14  1  0  0  0  0
 19 23  1  0  0  0  0
 22 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 22 31  1  0  0  0  0
 22 34  1  6  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  2  0  0  0  0
 26 24  1  0  0  0  0
 27 24  1  0  0  0  0
 30 25  1  0  0  0  0
 29 26  2  0  0  0  0
 31 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 28  1  0  0  0  0
 32 29  1  0  0  0  0
 33 30  2  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    8.8461    2.1203    2.3315 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6663    1.4943    1.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7043    0.6901    0.7541 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5968    0.0959    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4173    0.3308    0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3823    1.1506    2.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    1.3223    2.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5223    1.7288    2.5165 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.2870    0.5055 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501    0.0651    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1226   -0.9322   -0.1238 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103   -0.9325   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746    0.0671    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4529    0.0756    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.9193   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522   -0.9055   -0.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1677   -1.9713   -0.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2436    0.3156   -0.6444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6943    0.3180   -0.8021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3204    1.0300    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8091    1.1161    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4462   -0.1973    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8331   -1.2793    0.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8524   -0.2476    0.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9910    1.0028   -2.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576    1.4541   -2.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2962    1.1292   -2.5085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175   -1.9313   -1.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615   -1.9421   -0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -1.9152   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3881   -1.5275   -0.2681 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2810   -1.1100   -1.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5604   -0.7548   -0.8413 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0742    3.1013    2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5122    1.6095    2.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4980    2.3464    3.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    0.1073    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890    1.0614    0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365    0.8675    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    0.8810    0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381    1.2209   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195   -0.7364   -0.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8937    2.0595    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0464    0.5036    1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2162    1.7527   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1081    1.6515    1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3513   -1.0829    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6290    1.7715   -3.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8469   -2.7093   -1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6503   -2.7326   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -1.9841   -1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7511   -2.9052   -0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8846   -2.2492    0.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8067   -0.1764   -1.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3659   -1.9022   -2.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4685   -1.1097   -1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 11  1  0
 11 10  1  0
 10  9  1  0
  9  5  1  0
  5  4  2  0
  4 33  1  0
 33 32  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2  8  1  0
  8  6  1  0
  6  7  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 28  1  0
 28 29  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 19 25  1  0
 25 27  1  0
 25 26  2  0
  9 31  1  0
  6  5  1  0
 29 12  1  0
 32 31  1  0
 31 53  1  1
 30 51  1  0
 30 52  1  0
 10 37  1  0
 10 38  1  0
 33 56  1  0
 32 54  1  0
 32 55  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
 13 39  1  0
 14 40  1  0
 28 49  1  0
 29 50  1  0
 18 41  1  0
 19 42  1  6
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 24 47  1  0
 27 48  1  0
M  END


  Mrv0541 02241222382D          

 34 37  0  0  1  0            999 V2000
    4.2868    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0626    0.0000 C   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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4304    4.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7159    4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303    3.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1446    2.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1448    4.9498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -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
   -1.4292   -1.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8582   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291    0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  1  2  0  0  0  0
  8  1  1  0  0  0  0
  5  3  2  0  0  0  0
  3  8  1  0  0  0  0
  6  4  1  0  0  0  0
  4  8  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
 21  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 16  9  1  0  0  0  0
 15 10  1  0  0  0  0
 13 10  2  0  0  0  0
 18 10  1  0  0  0  0
 14 12  1  0  0  0  0
 12 17  1  1  0  0  0
 15 14  1  0  0  0  0
 19 23  1  0  0  0  0
 22 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 22 31  1  0  0  0  0
 22 34  1  6  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  2  0  0  0  0
 26 24  1  0  0  0  0
 27 24  1  0  0  0  0
 30 25  1  0  0  0  0
 29 26  2  0  0  0  0
 31 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 28  1  0  0  0  0
 32 29  1  0  0  0  0
 33 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0153165

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13+/m1/s1

> <INCHI_KEY>
QYNUQALWYRSVHF-OLZOCXBDSA-N

> <FORMULA>
C20H23N7O6

> <MOLECULAR_WEIGHT>
457.4399

> <EXACT_MASS>
457.170981503

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
45.75831886073985

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

> <ALOGPS_LOGP>
-0.94

> <JCHEM_LOGP>
-2.019855468407738

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.7382996772475683

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9303065927026704

> <JCHEM_PKA_STRONGEST_BASIC>
4.596941286239965

> <JCHEM_POLAR_SURFACE_AREA>
189.69

> <JCHEM_REFRACTIVITY>
123.9566

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,10-Methylene-THF

> <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  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.670   9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       9.336   3.850   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      13.337   9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -2.668  -3.080   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      -4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.668   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      -2.668   1.540   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
CONECT    1   17    2    8                                                  
CONECT    2    1                                                            
CONECT    3    5    8                                                       
CONECT    4    6    8                                                       
CONECT    5    3    7                                                       
CONECT    6    4    7                                                       
CONECT    7    5    6   21                                                  
CONECT    8    1    3    4                                                  
CONECT    9   11   12   16                                                  
CONECT   10   15   13   18                                                  
CONECT   11    9                                                            
CONECT   12    9   14   17                                                  
CONECT   13   10                                                            
CONECT   14   12   15                                                       
CONECT   15   10   14                                                       
CONECT   16    9                                                            
CONECT   17    1   12                                                       
CONECT   18   10                                                            
CONECT   19   23   21                                                       
CONECT   20   22   21                                                       
CONECT   21    7   20   19                                                  
CONECT   22   20   31   34   23                                             
CONECT   23   19   22   25                                                  
CONECT   24   25   26   27                                                  
CONECT   25   23   24   30                                                  
CONECT   26   24   29                                                       
CONECT   27   24   31                                                       
CONECT   28   29   30                                                       
CONECT   29   26   28   32                                                  
CONECT   30   25   28   33                                                  
CONECT   31   22   27                                                       
CONECT   32   29                                                            
CONECT   33   30                                                            
CONECT   34   22                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(6R)-5,10-Methylenetetrahydrofolate	ChEBI
5,10-Methylene-THF	ChEBI
5,10-Methylenetetrahydrofolate	ChEBI
5,10-Methylenetetrahydrofolic acid	ChEBI
(6R)-5,10-Methylenetetrahydrofolic acid	Generator

Chemical Formula

C₂₀H₂₃N₇O₆

Average Mass

457.4399 Da

Monoisotopic Mass

457.17098 Da

IUPAC Name

(2S)-2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

Traditional Name

5,10-Methylene-THF

CAS Registry Number

Not Available

SMILES

[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13+/m1/s1

InChI Key

QYNUQALWYRSVHF-OLZOCXBDSA-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

Not Available

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
Phenylimidazolidine
Alpha-amino acid or derivatives
Benzamide
Benzoic acid or derivatives
Imidazopyrazine
Benzoyl
Dialkylarylamine
Aniline or substituted anilines
Pyrimidone
Aminopyrimidine
Secondary aliphatic/aromatic amine
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Heteroaromatic compound
Vinylogous amide
Imidazolidine
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary amine
Azacycle
Carboxylic acid
Carboxylic acid derivative
Primary amine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5,10-methylenetetrahydrofolic acid (CHEBI:1989 )

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	-0.94	ALOGPS
logP	-2	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	189.69 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	123.96 m³·mol⁻¹	ChemAxon
Polarizability	45.76 Å³	ChemAxon
Number of Rings	4	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

DB12676

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007250

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5,10-Methylenetetrahydrofolate

METLIN ID

Not Available

PubChem Compound

445117

PDB ID

Not Available

ChEBI ID

1989

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid (NP0153165)

MOL for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

3D MOL for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

3D SDF for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

3D-SDF for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

PDB for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

3D PDB for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

SMILES for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

INCHI for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

Structure for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)

3D Structure for NP0153165 ((2s)-2-({4-[(6ar)-1-hydroxy-3-imino-4h,5h,6h,6ah,7h,9h-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid)