MiMeDB: Showing metabocard for 5,10-Methylene-THF (MMDBc0029630)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:35:20 UTC

Update Date

2022-08-31 14:15:02 UTC

Metabolite ID

MMDBc0029630

Metabolite Identification

Common Name

5,10-Methylene-THF

Description

5,10-Methylene-THF is an intermediate in the metabolism of methane and the metabolism of nitrogen. 5,10-Methylenetetrahydrofolate (5,10-CH2-THF) is the substrate used by the enzyme methylenetetrahydrofolate reductase (MTHFR) to generate 5-methyltetrahydrofolate (5-MTHF, or levomefolic acid). 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. Methylenetetrahydrofolate reductase catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a cosubstrate for homocysteine remethylation to methionine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000242D          

 34 37  0  0  1  0            999 V2000
    8.2704   -5.4557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5472   -5.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0788   -5.0032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2704   -6.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5472   -4.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275   -5.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5461   -5.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0752   -4.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1077   -6.5179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -3.7923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275   -3.8028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -5.0392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275   -6.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8203   -6.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -4.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1692   -6.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333   -7.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -3.8028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0637   -6.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0602   -7.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4732   -6.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1857   -6.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232   -6.8957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1857   -5.6411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0318   -6.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7409   -6.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0318   -5.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4535   -6.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7445   -5.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3227   -5.2563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1625   -6.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1513   -7.7183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8717   -6.4890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9092   -4.7720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  6  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  2  0  0  0  0
  9 14  1  0  0  0  0
 11 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  1  0  0  0  0
 16 19  2  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 12 15  1  0  0  0  0
 20 21  2  0  0  0  0
  3 34  1  1  0  0  0
M  END

HMDB0001533
     RDKit          3D
5,10-Methylene-THF
 56 59  0  0  0  0  0  0  0  0999 V2000
   -9.4210   -1.0914   -0.4443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0704   -0.7433   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7611    0.0428    0.8807 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4877    0.3907    1.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345   -0.0556    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7650   -0.8579   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8271   -1.2624   -1.4179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0508   -1.1737   -0.9388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083    0.3143    0.6825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8654    0.0459   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    0.9880    0.4970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5123    0.9560    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    1.9018    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265    1.8202    0.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903    0.7772   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168    0.6575   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.6592   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -0.5942   -0.6701 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7126   -0.6734   -0.9008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3015   -1.6475    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7710   -1.8422   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396   -0.5904    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7898   -0.6889    0.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9355    0.5763    0.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9090   -1.0997   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9140   -1.3491   -3.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1615   -1.2320   -2.8658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443   -0.1888   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652   -0.0992   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415    1.9746    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371    1.0882    1.8459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8669    1.8662    2.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1480    1.2197    2.2688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5988   -1.7072   -1.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2329   -0.7739    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2651   -1.7868   -1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -1.0081    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    0.2308   -1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    2.7340    1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636    2.5846    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387   -1.4820   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1505    0.3177   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -2.6110   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057   -1.3086    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331   -2.6250    0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0297   -2.2088   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947    0.7992    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4376   -2.0971   -3.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333   -1.0510   -1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320   -0.9006   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0846    2.7465    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741    2.4705    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413    0.3979    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6734    1.9240    3.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288    2.8974    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8732    1.3686    3.0066 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  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  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 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  2  0
 25 27  1  0
 15 28  1  0
 28 29  2  0
 11 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
  8  2  1  0
 31  9  1  0
 33  4  1  0
 29 12  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 13 39  1  0
 14 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 24 47  1  0
 27 48  1  0
 28 49  1  0
 29 50  1  0
 30 51  1  0
 30 52  1  0
 31 53  1  1
 32 54  1  0
 32 55  1  0
 33 56  1  0
M  END


  Mrv1652309042000242D          

 34 37  0  0  1  0            999 V2000
    8.2704   -5.4557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5472   -5.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0788   -5.0032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2704   -6.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5472   -4.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275   -5.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5461   -5.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0752   -4.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1077   -6.5179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -3.7923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275   -3.8028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -5.0392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275   -6.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8203   -6.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -4.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1692   -6.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333   -7.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -3.8028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0637   -6.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0602   -7.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4732   -6.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1857   -6.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232   -6.8957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1857   -5.6411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0318   -6.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7409   -6.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0318   -5.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4535   -6.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7445   -5.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3227   -5.2563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1625   -6.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1513   -7.7183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8717   -6.4890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9092   -4.7720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  6  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  2  0  0  0  0
  9 14  1  0  0  0  0
 11 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  1  0  0  0  0
 16 19  2  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 12 15  1  0  0  0  0
 20 21  2  0  0  0  0
  3 34  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029630

> <DATABASE_NAME>
MIME

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

> <FORMULA>
C20H23N7O6

> <MOLECULAR_WEIGHT>
457.4399

> <EXACT_MASS>
457.170981503

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
46.121777568754574

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.94

> <JCHEM_LOGP>
-2.5554683402543046

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.8086133308206467

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.005887206521458

> <JCHEM_PKA_STRONGEST_BASIC>
5.611442082182131

> <JCHEM_POLAR_SURFACE_AREA>
190.67999999999998

> <JCHEM_REFRACTIVITY>
134.77110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({4-[(6aR)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001533
     RDKit          3D
5,10-Methylene-THF
 56 59  0  0  0  0  0  0  0  0999 V2000
   -9.4210   -1.0914   -0.4443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0704   -0.7433   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7611    0.0428    0.8807 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4877    0.3907    1.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345   -0.0556    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7650   -0.8579   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8271   -1.2624   -1.4179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0508   -1.1737   -0.9388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083    0.3143    0.6825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8654    0.0459   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    0.9880    0.4970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5123    0.9560    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    1.9018    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265    1.8202    0.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903    0.7772   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168    0.6575   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.6592   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -0.5942   -0.6701 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7126   -0.6734   -0.9008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3015   -1.6475    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7710   -1.8422   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396   -0.5904    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7898   -0.6889    0.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9355    0.5763    0.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9090   -1.0997   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9140   -1.3491   -3.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1615   -1.2320   -2.8658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443   -0.1888   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652   -0.0992   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415    1.9746    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371    1.0882    1.8459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8669    1.8662    2.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1480    1.2197    2.2688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5988   -1.7072   -1.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2329   -0.7739    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2651   -1.7868   -1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -1.0081    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    0.2308   -1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    2.7340    1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636    2.5846    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387   -1.4820   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1505    0.3177   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -2.6110   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057   -1.3086    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331   -2.6250    0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0297   -2.2088   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947    0.7992    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4376   -2.0971   -3.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333   -1.0510   -1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320   -0.9006   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0846    2.7465    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741    2.4705    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413    0.3979    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6734    1.9240    3.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288    2.8974    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8732    1.3686    3.0066 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  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  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 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  2  0
 25 27  1  0
 15 28  1  0
 28 29  2  0
 11 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
  8  2  1  0
 31  9  1  0
 33  4  1  0
 29 12  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 13 39  1  0
 14 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 24 47  1  0
 27 48  1  0
 28 49  1  0
 29 50  1  0
 30 51  1  0
 30 52  1  0
 31 53  1  1
 32 54  1  0
 32 55  1  0
 33 56  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0      15.438 -10.184   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      14.088  -9.407   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.947  -9.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.438 -11.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.088  -7.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.745 -10.191   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.819 -10.730   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.940  -7.776   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      17.001 -12.167   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      15.431  -7.079   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      12.745  -7.099   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      11.421  -9.407   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      12.745 -11.721   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      18.331 -12.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.421  -7.863   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.983 -11.462   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.102 -14.148   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.091  -7.099   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      20.652 -11.481   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.646 -14.148   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.417 -12.818   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.747 -12.060   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      24.310 -12.872   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0      22.747 -10.530   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      26.193 -12.106   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.516 -12.879   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.193 -10.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.847 -12.113   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      27.523  -9.818   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      24.869  -9.812   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      30.170 -12.885   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      30.149 -14.407   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      31.494 -12.113   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      18.497  -8.908   0.000  0.00  0.00           H+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8   34                                             
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12   13                                                  
CONECT    7    3    9                                                       
CONECT    8    3   10                                                       
CONECT    9    4   14    7                                                  
CONECT   10    5    8                                                       
CONECT   11    5   15                                                       
CONECT   12    6   15                                                       
CONECT   13    6                                                            
CONECT   14    9   16   17                                                  
CONECT   15   11   18   12                                                  
CONECT   16   14   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15                                                            
CONECT   19   16   21                                                       
CONECT   20   17   21                                                       
CONECT   21   19   22   20                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25   29   30                                                  
CONECT   28   26   31                                                       
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    3                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0001533
HETATM    1  N1  UNL     1      -9.421  -1.091  -0.444  1.00  0.00           N  
HETATM    2  C1  UNL     1      -8.070  -0.743  -0.173  1.00  0.00           C  
HETATM    3  N2  UNL     1      -7.761   0.043   0.881  1.00  0.00           N  
HETATM    4  C2  UNL     1      -6.488   0.391   1.166  1.00  0.00           C  
HETATM    5  C3  UNL     1      -5.434  -0.056   0.372  1.00  0.00           C  
HETATM    6  C4  UNL     1      -5.765  -0.858  -0.701  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.827  -1.262  -1.418  1.00  0.00           O  
HETATM    8  N3  UNL     1      -7.051  -1.174  -0.939  1.00  0.00           N  
HETATM    9  N4  UNL     1      -4.108   0.314   0.682  1.00  0.00           N  
HETATM   10  C5  UNL     1      -2.865   0.046  -0.015  1.00  0.00           C  
HETATM   11  N5  UNL     1      -1.904   0.988   0.497  1.00  0.00           N  
HETATM   12  C6  UNL     1      -0.512   0.956   0.318  1.00  0.00           C  
HETATM   13  C7  UNL     1       0.374   1.902   0.792  1.00  0.00           C  
HETATM   14  C8  UNL     1       1.726   1.820   0.595  1.00  0.00           C  
HETATM   15  C9  UNL     1       2.290   0.777  -0.095  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.717   0.658  -0.329  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.456   1.659  -0.228  1.00  0.00           O  
HETATM   18  N6  UNL     1       4.260  -0.594  -0.670  1.00  0.00           N  
HETATM   19  C11 UNL     1       5.713  -0.673  -0.901  1.00  0.00           C  
HETATM   20  C12 UNL     1       6.302  -1.648   0.094  1.00  0.00           C  
HETATM   21  C13 UNL     1       7.771  -1.842  -0.002  1.00  0.00           C  
HETATM   22  C14 UNL     1       8.540  -0.590   0.227  1.00  0.00           C  
HETATM   23  O3  UNL     1       9.790  -0.689   0.043  1.00  0.00           O  
HETATM   24  O4  UNL     1       7.935   0.576   0.610  1.00  0.00           O  
HETATM   25  C15 UNL     1       5.909  -1.100  -2.305  1.00  0.00           C  
HETATM   26  O5  UNL     1       4.914  -1.349  -3.016  1.00  0.00           O  
HETATM   27  O6  UNL     1       7.162  -1.232  -2.866  1.00  0.00           O  
HETATM   28  C16 UNL     1       1.444  -0.189  -0.586  1.00  0.00           C  
HETATM   29  C17 UNL     1       0.065  -0.099  -0.382  1.00  0.00           C  
HETATM   30  C18 UNL     1      -2.642   1.975   1.240  1.00  0.00           C  
HETATM   31  C19 UNL     1      -3.737   1.088   1.846  1.00  0.00           C  
HETATM   32  C20 UNL     1      -4.867   1.866   2.430  1.00  0.00           C  
HETATM   33  N7  UNL     1      -6.148   1.220   2.269  1.00  0.00           N  
HETATM   34  H1  UNL     1      -9.599  -1.707  -1.262  1.00  0.00           H  
HETATM   35  H2  UNL     1     -10.233  -0.774   0.115  1.00  0.00           H  
HETATM   36  H3  UNL     1      -7.265  -1.787  -1.765  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.548  -1.008   0.096  1.00  0.00           H  
HETATM   38  H5  UNL     1      -2.954   0.231  -1.114  1.00  0.00           H  
HETATM   39  H6  UNL     1      -0.092   2.734   1.344  1.00  0.00           H  
HETATM   40  H7  UNL     1       2.364   2.585   0.987  1.00  0.00           H  
HETATM   41  H8  UNL     1       3.739  -1.482  -0.775  1.00  0.00           H  
HETATM   42  H9  UNL     1       6.151   0.318  -0.783  1.00  0.00           H  
HETATM   43  H10 UNL     1       5.744  -2.611  -0.041  1.00  0.00           H  
HETATM   44  H11 UNL     1       6.006  -1.309   1.132  1.00  0.00           H  
HETATM   45  H12 UNL     1       8.133  -2.625   0.730  1.00  0.00           H  
HETATM   46  H13 UNL     1       8.030  -2.209  -1.011  1.00  0.00           H  
HETATM   47  H14 UNL     1       7.795   0.799   1.570  1.00  0.00           H  
HETATM   48  H15 UNL     1       7.438  -2.097  -3.357  1.00  0.00           H  
HETATM   49  H16 UNL     1       1.833  -1.051  -1.154  1.00  0.00           H  
HETATM   50  H17 UNL     1      -0.532  -0.901  -0.801  1.00  0.00           H  
HETATM   51  H18 UNL     1      -3.085   2.746   0.578  1.00  0.00           H  
HETATM   52  H19 UNL     1      -2.074   2.471   2.032  1.00  0.00           H  
HETATM   53  H20 UNL     1      -3.241   0.398   2.552  1.00  0.00           H  
HETATM   54  H21 UNL     1      -4.673   1.924   3.541  1.00  0.00           H  
HETATM   55  H22 UNL     1      -4.829   2.897   2.067  1.00  0.00           H  
HETATM   56  H23 UNL     1      -6.873   1.369   3.007  1.00  0.00           H  
CONECT    1    2   34   35
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5   33
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   36
CONECT    9   10   31
CONECT   10   11   37   38
CONECT   11   12   30
CONECT   12   13   13   29
CONECT   13   14   39
CONECT   14   15   15   40
CONECT   15   16   28
CONECT   16   17   17   18
CONECT   18   19   41
CONECT   19   20   25   42
CONECT   20   21   43   44
CONECT   21   22   45   46
CONECT   22   23   23   24
CONECT   24   47
CONECT   25   26   26   27
CONECT   27   48
CONECT   28   29   29   49
CONECT   29   50
CONECT   30   31   51   52
CONECT   31   32   53
CONECT   32   33   54   55
CONECT   33   56
END

HMDB0001533
     RDKit          3D
5,10-Methylene-THF
 56 59  0  0  0  0  0  0  0  0999 V2000
   -9.4210   -1.0914   -0.4443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0704   -0.7433   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7611    0.0428    0.8807 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4877    0.3907    1.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345   -0.0556    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7650   -0.8579   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8271   -1.2624   -1.4179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0508   -1.1737   -0.9388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083    0.3143    0.6825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8654    0.0459   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    0.9880    0.4970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5123    0.9560    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    1.9018    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265    1.8202    0.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903    0.7772   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168    0.6575   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    1.6592   -0.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -0.5942   -0.6701 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7126   -0.6734   -0.9008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3015   -1.6475    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7710   -1.8422   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396   -0.5904    0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7898   -0.6889    0.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9355    0.5763    0.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9090   -1.0997   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9140   -1.3491   -3.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1615   -1.2320   -2.8658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443   -0.1888   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652   -0.0992   -0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415    1.9746    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371    1.0882    1.8459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8669    1.8662    2.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1480    1.2197    2.2688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5988   -1.7072   -1.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2329   -0.7739    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2651   -1.7868   -1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -1.0081    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    0.2308   -1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    2.7340    1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636    2.5846    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387   -1.4820   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1505    0.3177   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -2.6110   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057   -1.3086    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331   -2.6250    0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0297   -2.2088   -1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947    0.7992    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4376   -2.0971   -3.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333   -1.0510   -1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320   -0.9006   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0846    2.7465    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741    2.4705    2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413    0.3979    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6734    1.9240    3.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288    2.8974    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8732    1.3686    3.0066 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  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  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 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  2  0
 25 27  1  0
 15 28  1  0
 28 29  2  0
 11 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
  8  2  1  0
 31  9  1  0
 33  4  1  0
 29 12  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 13 39  1  0
 14 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 24 47  1  0
 27 48  1  0
 28 49  1  0
 29 50  1  0
 30 51  1  0
 30 52  1  0
 31 53  1  1
 32 54  1  0
 32 55  1  0
 33 56  1  0
M  END

Synonyms

Value	Source
(6R)-5,10-Methylenetetrahydrofolate	Kegg
(6R)-5,10-Methylenetetrahydrofolic acid	Generator
5,10-Methenyltetrahydropteroylglutamate	HMDB
5,10-Methylene-6-hydrofolate	HMDB
5,10-Methylene-6-hydrofolic acid	HMDB
5,10-Methylenetetrahydrofolate	HMDB
5,10-Methylenetetrahydrofolic acid	HMDB
N5>,N10-methylenetetrahydrofolate	HMDB
5,10-Methylene-5,6,7,8-tetrahydrofolate	HMDB
Tetrahydromethylenefolate	HMDB
5,10-Methylenetetrahydrofolate, (D-glu)-isomer	HMDB
CH2H4Folate	HMDB
5,10-Methylenetetrahydrofolate monohydrochloride, (L-glu)-isomer	HMDB
5,10-Methylenetetrahydrofolate, (L-glu)-(S)-isomer	HMDB

Molecular Formula

C₂₀H₂₃N₇O₆

Average Mass

457.4399

Monoisotopic Mass

457.170981503

IUPAC Name

2-({4-[(6aR)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

Traditional Name

2-({4-[(6aR)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

CAS Registry Number

31690-11-6

SMILES

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

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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	-0.94	ALOGPS
logP	-2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	5.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	190.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.77 m³·mol⁻¹	ChemAxon
Polarizability	46.12 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1635900000-4b2ed6618451a7e931b1	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-001i-2129050000-80e96fb3203322200945	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08fu-0003900000-ce1f75a98c0216d169e2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0229400000-c8c29bf14ef80a73f864	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02u3-1192000000-ab556f50884c7b4fdcbe	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0001900000-6ba3ddeb1f652fdc6b6b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-1225900000-82b75909f87dfeb54211	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9553000000-5aca24c246430955de51	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0006900000-dd6e195db40930799024	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0109200000-aa6336e6c1c41c98d390	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-1695000000-8b9546bbad524392a35b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-0009800000-1ef964ba403eb61f6bf0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01w3-1407900000-f4b4d0db119b458049fb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-5935200000-5fa8390660d5a558ac8b	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood
Feces

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
MMDBp0191859	Methylenetetrahydrofolate reductase	Unknown	P42898	Homo sapiens
MMDBp0192327	Aminomethyltransferase, mitochondrial	Enzyme	P48728	Homo sapiens
MMDBp0192412	Serine hydroxymethyltransferase, mitochondrial	Enzyme	P34897	Homo sapiens
MMDBp0192414	Serine hydroxymethyltransferase, cytosolic	Enzyme	P34896	Homo sapiens
MMDBp0192538	Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial	Unknown	P13995	Homo sapiens
MMDBp0192541	C-1-tetrahydrofolate synthase, cytoplasmic	Enzyme	P11586	Homo sapiens
MMDBp0193789	Glycine cleavage system H protein, mitochondrial	Enzyme	P23434	Homo sapiens
MMDBp0193968	Thymidylate synthase	Enzyme	P04818	Homo sapiens
MMDBp0194061	Probable bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase 2	Unknown	Q9H903	Homo sapiens
MMDBp0194163	Monofunctional C1-tetrahydrofolate synthase, mitochondrial	Enzyme	Q6UB35	Homo sapiens
MMDBp0194164	Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	Enzyme	Q7Z650	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000683	5-Methyltetrahydrofolic acid	5,10-Methylene-THF	Not Available	VMH	3735413
MMDBr0001273	S(8)-aminomethyldihydrolipoamide	Dihydrolipoamide	aminomethyltransferase	VMH	15355973
MMDBr0001305	L-Serine	Glycine	serine hydroxymethyltransferase 1 (soluble)	VMH; KEGG	8505317 8611185 9038835
MMDBr0001691	5,10-Methylene-THF	5,10-Methenyltetrahydrofolic acid	methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	VMH; KEGG	30371894
MMDBr0001692	5,10-Methylene-THF	5,10-Methenyltetrahydrofolic acid	methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 1, methenyltetrahydrofolate cyclohydrolase, formyltetrahydrofolate synthetase	VMH; KEGG	30371894
MMDBr0002094	Sarcosine	Glycine	sarcosine dehydrogenase	VMH	10444331
MMDBr0005500	5,10-Methylene-THF	5-Methyltetrahydrofolic acid	methylenetetrahydrofolate reductase (NAD(P)H)	VMH; KEGG	30371894
MMDBr0006743	Formaldehyde	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0007126	5-Methyltetrahydrofolic acid	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0007202	alpha-Ketoisovaleric acid	2-Dehydropantoate	Not Available	VMH	30371894
MMDBr0007427	L-Serine	Glycine	Not Available	VMH; KEGG	30371894
MMDBr0007493	5,10-Methylene-THF	5,10-Methenyltetrahydrofolic acid	Not Available	VMH; KEGG	30371894
MMDBr0007980	dUMP	Dihydrofolic acid	Not Available	VMH; KEGG	30371894
MMDBr0008016	5-Methyltetrahydrofolic acid	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0008126	dUMP	5-Thymidylic acid	Not Available	VMH	30371894
MMDBr0008135	5,10-Methylene-THF	5,10-Methenyltetrahydrofolic acid	Not Available	VMH	30371894
MMDBr0008291	Glycine	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0010939	L-Serine	Glycine	Not Available	VMH	30371894
MMDBr0011016	dUMP	5-Thymidylic acid	Not Available	VMH	30371894

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	Microbial Links
Bacteria	Proteobacteria	182	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	391	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	128	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.01		0.0	0.21	uM	Adult (>18 years old)	Both	Normal	HMDB	18160726

External Links

HMDB ID

HMDB0001533

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

34022

Wikipedia Link

Not Available

METLIN ID

6304

PubChem Compound

439175

PDB ID

Not Available

ChEBI ID

15636

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 5,10-Methylene-THF (MMDBc0029630)

MOL for #<Metabolite:0x00007fdb1ca939c8>

3D MOL for #<Metabolite:0x00007fdb1ca939c8>

3D SDF for #<Metabolite:0x00007fdb1ca939c8>

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3D PDB for #<Metabolite:0x00007fdb1ca939c8>

SMILES for #<Metabolite:0x00007fdb1ca939c8>

INCHI for #<Metabolite:0x00007fdb1ca939c8>

Structure for #<Metabolite:0x00007fdb1ca939c8>

3D Structure for #<Metabolite:0x00007fdb1ca939c8>