MiMeDB: Showing metabocard for Dihydrofolic acid (MMDBc0029538)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:31:29 UTC

Update Date

2022-08-31 13:42:51 UTC

Metabolite ID

MMDBc0029538

Metabolite Identification

Common Name

Dihydrofolic acid

Description

Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division. It can be targeted with drug analogs to prevent nucleic acid synthesis. Dihydrofolic acid is also known by the name Dihydrofolate - more commonly Vitamin B9.

Structure

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


  Mrv1652304181917202D          

 32 34  0  0  0  0            999 V2000
 9995.336410000.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1901 9999.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9046 9999.1801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.762410000.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.476010000.4166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.191710000.8291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.905310000.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.621010000.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.336710000.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.050310000.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.3367 9999.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.191710001.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.905310002.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.476010002.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.762410001.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9096 9997.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3356 9999.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6211 9999.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6211 9998.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3356 9997.9395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0501 9998.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0501 9999.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7646 9997.9394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4790 9998.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4791 9999.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7645 9999.5895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.048810000.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.334310000.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.619810000.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6198 9999.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3342 9999.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0488 9999.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 17 22  1  0  0  0  0
 21 22  2  0  0  0  0
 24 25  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 27  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 25 26  2  0  0  0  0
 22 26  1  0  0  0  0
 23 24  1  0  0  0  0
 21 23  1  0  0  0  0
 19 16  1  0  0  0  0
 25  2  1  0  0  0  0
  1 17  2  0  0  0  0
 27  4  1  0  0  0  0
  3 30  1  0  0  0  0
M  END

HMDB0001056
     RDKit          3D
Dihydrofolic acid
 53 55  0  0  0  0  0  0  0  0999 V2000
    7.2146    3.0642   -1.8085 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4818    1.9522   -1.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637    0.8279   -2.0499 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6769   -0.2428   -1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -1.2875   -2.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709   -0.1881   -0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1922    0.9562    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927    1.9877   -0.1089 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5679    0.9951    1.6569 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176   -0.0805    2.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -1.2641    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204   -2.4497    1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759   -2.1942    2.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705   -1.7209    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004   -1.5985   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019   -1.1198   -0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4334   -0.7213   -0.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719   -0.2240   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -0.4203   -2.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820    0.4482   -0.6542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105    0.9420   -1.5049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8243    0.1069   -1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6296   -0.2507   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0323   -1.0952    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9252   -1.6582    0.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7017   -1.3218    1.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9461    2.3663   -1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3669    3.0209   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9326    2.9455   -2.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -0.8398    1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -1.3240    1.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315   -1.2700    0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1180    3.2991   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8180    3.5996   -2.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9894    2.8717    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600    1.8690    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2740   -0.3819    3.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7772    0.2506    2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -3.2349    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -2.8943    2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -2.3680    3.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442   -1.9046   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0587   -1.0378   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.6161    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1360    0.9624   -2.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4821    0.6581   -2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -0.7985   -2.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0471    0.6608    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5703   -0.7523   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7362   -0.5292    2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0327    2.7237   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254   -0.5417    1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -1.4096    2.9261 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 11 32  2  0
  8  2  1  0
 31 14  1  0
 32  6  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 20 44  1  0
 21 45  1  6
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 26 50  1  0
 29 51  1  0
 30 52  1  0
 31 53  1  0
M  END


  Mrv1652304181917202D          

 32 34  0  0  0  0            999 V2000
 9995.336410000.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1901 9999.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9046 9999.1801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.762410000.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.476010000.4166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.191710000.8291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.905310000.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.621010000.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.336710000.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.050310000.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.3367 9999.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.191710001.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.905310002.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.476010002.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.762410001.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9096 9997.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3356 9999.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6211 9999.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6211 9998.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3356 9997.9395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0501 9998.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0501 9999.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7646 9997.9394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4790 9998.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4791 9999.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7645 9999.5895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.048810000.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.334310000.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.619810000.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6198 9999.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3342 9999.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0488 9999.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 17 22  1  0  0  0  0
 21 22  2  0  0  0  0
 24 25  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 27  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 25 26  2  0  0  0  0
 22 26  1  0  0  0  0
 23 24  1  0  0  0  0
 21 23  1  0  0  0  0
 19 16  1  0  0  0  0
 25  2  1  0  0  0  0
  1 17  2  0  0  0  0
 27  4  1  0  0  0  0
  3 30  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029538

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1

> <INCHI_KEY>
OZRNSSUDZOLUSN-LBPRGKRZSA-N

> <FORMULA>
C19H21N7O6

> <MOLECULAR_WEIGHT>
443.4133

> <EXACT_MASS>
443.155331439

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.310029663024785

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <ALOGPS_LOGP>
-0.93

> <JCHEM_LOGP>
-1.7816132694652138

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.17230491299049

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.373110634106839

> <JCHEM_PKA_STRONGEST_BASIC>
2.0926310636850247

> <JCHEM_POLAR_SURFACE_AREA>
207.60000000000002

> <JCHEM_REFRACTIVITY>
120.9914

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrofolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001056
     RDKit          3D
Dihydrofolic acid
 53 55  0  0  0  0  0  0  0  0999 V2000
    7.2146    3.0642   -1.8085 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4818    1.9522   -1.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637    0.8279   -2.0499 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6769   -0.2428   -1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -1.2875   -2.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709   -0.1881   -0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1922    0.9562    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927    1.9877   -0.1089 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5679    0.9951    1.6569 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176   -0.0805    2.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -1.2641    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204   -2.4497    1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759   -2.1942    2.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705   -1.7209    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004   -1.5985   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019   -1.1198   -0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4334   -0.7213   -0.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719   -0.2240   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -0.4203   -2.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820    0.4482   -0.6542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105    0.9420   -1.5049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8243    0.1069   -1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6296   -0.2507   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0323   -1.0952    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9252   -1.6582    0.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7017   -1.3218    1.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9461    2.3663   -1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3669    3.0209   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9326    2.9455   -2.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -0.8398    1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -1.3240    1.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315   -1.2700    0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1180    3.2991   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8180    3.5996   -2.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9894    2.8717    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600    1.8690    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2740   -0.3819    3.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7772    0.2506    2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -3.2349    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -2.8943    2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -2.3680    3.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442   -1.9046   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0587   -1.0378   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.6161    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1360    0.9624   -2.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4821    0.6581   -2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -0.7985   -2.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0471    0.6608    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5703   -0.7523   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7362   -0.5292    2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0327    2.7237   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254   -0.5417    1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -1.4096    2.9261 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 11 32  2  0
  8  2  1  0
 31 14  1  0
 32  6  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 20 44  1  0
 21 45  1  6
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 26 50  1  0
 29 51  1  0
 30 52  1  0
 31 53  1  0
M  END

HEADER    PROTEIN                                 18-APR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-19         0                                  
HETATM    1  O   UNK     0    8657.9618667.452   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8663.2888665.904   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8664.6228665.136   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8669.9568668.214   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8671.2898667.444   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8672.6258668.214   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8673.9578667.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.2938668.214   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8676.6298667.444   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8677.9618668.214   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8676.6298665.904   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8672.6258669.754   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8673.9578670.524   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8671.2898670.524   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8669.9568669.754   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0    8655.2988662.813   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8657.9608665.900   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    8656.6268665.130   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    8656.6268663.590   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8657.9608662.820   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8659.2948663.590   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8659.2948665.130   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0    8660.6278662.820   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0    8661.9618663.590   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8661.9618665.130   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0    8660.6278665.900   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0    8668.6248667.445   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8667.2918668.215   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8665.9578667.445   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8665.9578665.905   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8667.2918665.135   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8668.6248665.905   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    3   25                                                       
CONECT    3    2   30                                                       
CONECT    4    5   15   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    4                                                            
CONECT   16   19                                                            
CONECT   17   22   18    1                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   16                                                  
CONECT   20   19   21                                                       
CONECT   21   22   20   23                                                  
CONECT   22   17   21   26                                                  
CONECT   23   24   21                                                       
CONECT   24   25   23                                                       
CONECT   25   24   26    2                                                  
CONECT   26   25   22                                                       
CONECT   27   28   32    4                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31    3                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0001056
HETATM    1  N1  UNL     1       7.215   3.064  -1.808  1.00  0.00           N  
HETATM    2  C1  UNL     1       6.482   1.952  -1.310  1.00  0.00           C  
HETATM    3  N2  UNL     1       6.364   0.828  -2.050  1.00  0.00           N  
HETATM    4  C2  UNL     1       5.677  -0.243  -1.613  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.554  -1.287  -2.275  1.00  0.00           O  
HETATM    6  C3  UNL     1       5.071  -0.188  -0.362  1.00  0.00           C  
HETATM    7  C4  UNL     1       5.192   0.956   0.388  1.00  0.00           C  
HETATM    8  N3  UNL     1       5.893   1.988  -0.109  1.00  0.00           N  
HETATM    9  N4  UNL     1       4.568   0.995   1.657  1.00  0.00           N  
HETATM   10  C5  UNL     1       3.818  -0.081   2.226  1.00  0.00           C  
HETATM   11  C6  UNL     1       3.759  -1.264   1.314  1.00  0.00           C  
HETATM   12  C7  UNL     1       3.020  -2.450   1.782  1.00  0.00           C  
HETATM   13  N5  UNL     1       1.676  -2.194   2.210  1.00  0.00           N  
HETATM   14  C8  UNL     1       0.671  -1.721   1.342  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.800  -1.599  -0.021  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.202  -1.120  -0.821  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.433  -0.721  -0.295  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.472  -0.224  -1.183  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.332  -0.420  -2.433  1.00  0.00           O  
HETATM   20  N6  UNL     1      -3.582   0.448  -0.654  1.00  0.00           N  
HETATM   21  C13 UNL     1      -4.611   0.942  -1.505  1.00  0.00           C  
HETATM   22  C14 UNL     1      -5.824   0.107  -1.686  1.00  0.00           C  
HETATM   23  C15 UNL     1      -6.630  -0.251  -0.507  1.00  0.00           C  
HETATM   24  C16 UNL     1      -6.032  -1.095   0.511  1.00  0.00           C  
HETATM   25  O3  UNL     1      -4.925  -1.658   0.387  1.00  0.00           O  
HETATM   26  O4  UNL     1      -6.702  -1.322   1.724  1.00  0.00           O  
HETATM   27  C17 UNL     1      -4.946   2.366  -1.251  1.00  0.00           C  
HETATM   28  O5  UNL     1      -4.367   3.021  -0.383  1.00  0.00           O  
HETATM   29  O6  UNL     1      -5.933   2.946  -2.018  1.00  0.00           O  
HETATM   30  C18 UNL     1      -1.576  -0.840   1.070  1.00  0.00           C  
HETATM   31  C19 UNL     1      -0.556  -1.324   1.859  1.00  0.00           C  
HETATM   32  N7  UNL     1       4.332  -1.270   0.170  1.00  0.00           N  
HETATM   33  H1  UNL     1       8.118   3.299  -1.354  1.00  0.00           H  
HETATM   34  H2  UNL     1       6.818   3.600  -2.609  1.00  0.00           H  
HETATM   35  H3  UNL     1       5.989   2.872   0.465  1.00  0.00           H  
HETATM   36  H4  UNL     1       4.660   1.869   2.217  1.00  0.00           H  
HETATM   37  H5  UNL     1       4.274  -0.382   3.188  1.00  0.00           H  
HETATM   38  H6  UNL     1       2.777   0.251   2.407  1.00  0.00           H  
HETATM   39  H7  UNL     1       3.018  -3.235   0.986  1.00  0.00           H  
HETATM   40  H8  UNL     1       3.622  -2.894   2.623  1.00  0.00           H  
HETATM   41  H9  UNL     1       1.431  -2.368   3.210  1.00  0.00           H  
HETATM   42  H10 UNL     1       1.744  -1.905  -0.482  1.00  0.00           H  
HETATM   43  H11 UNL     1      -0.059  -1.038  -1.900  1.00  0.00           H  
HETATM   44  H12 UNL     1      -3.647   0.616   0.364  1.00  0.00           H  
HETATM   45  H13 UNL     1      -4.136   0.962  -2.554  1.00  0.00           H  
HETATM   46  H14 UNL     1      -6.482   0.658  -2.413  1.00  0.00           H  
HETATM   47  H15 UNL     1      -5.498  -0.799  -2.283  1.00  0.00           H  
HETATM   48  H16 UNL     1      -7.047   0.661   0.025  1.00  0.00           H  
HETATM   49  H17 UNL     1      -7.570  -0.752  -0.899  1.00  0.00           H  
HETATM   50  H18 UNL     1      -6.736  -0.529   2.354  1.00  0.00           H  
HETATM   51  H19 UNL     1      -6.033   2.724  -3.002  1.00  0.00           H  
HETATM   52  H20 UNL     1      -2.525  -0.542   1.521  1.00  0.00           H  
HETATM   53  H21 UNL     1      -0.687  -1.410   2.926  1.00  0.00           H  
CONECT    1    2   33   34
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   32
CONECT    7    8    9
CONECT    8   35
CONECT    9   10   36
CONECT   10   11   37   38
CONECT   11   12   32   32
CONECT   12   13   39   40
CONECT   13   14   41
CONECT   14   15   15   31
CONECT   15   16   42
CONECT   16   17   17   43
CONECT   17   18   30
CONECT   18   19   19   20
CONECT   20   21   44
CONECT   21   22   27   45
CONECT   22   23   46   47
CONECT   23   24   48   49
CONECT   24   25   25   26
CONECT   26   50
CONECT   27   28   28   29
CONECT   29   51
CONECT   30   31   31   52
CONECT   31   53
END

HMDB0001056
     RDKit          3D
Dihydrofolic acid
 53 55  0  0  0  0  0  0  0  0999 V2000
    7.2146    3.0642   -1.8085 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4818    1.9522   -1.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637    0.8279   -2.0499 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6769   -0.2428   -1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -1.2875   -2.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709   -0.1881   -0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1922    0.9562    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927    1.9877   -0.1089 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5679    0.9951    1.6569 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176   -0.0805    2.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -1.2641    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204   -2.4497    1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759   -2.1942    2.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705   -1.7209    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004   -1.5985   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019   -1.1198   -0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4334   -0.7213   -0.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719   -0.2240   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -0.4203   -2.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820    0.4482   -0.6542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105    0.9420   -1.5049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8243    0.1069   -1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6296   -0.2507   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0323   -1.0952    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9252   -1.6582    0.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7017   -1.3218    1.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9461    2.3663   -1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3669    3.0209   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9326    2.9455   -2.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -0.8398    1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -1.3240    1.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315   -1.2700    0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1180    3.2991   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8180    3.5996   -2.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9894    2.8717    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600    1.8690    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2740   -0.3819    3.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7772    0.2506    2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -3.2349    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -2.8943    2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -2.3680    3.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442   -1.9046   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0587   -1.0378   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.6161    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1360    0.9624   -2.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4821    0.6581   -2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -0.7985   -2.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0471    0.6608    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5703   -0.7523   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7362   -0.5292    2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0327    2.7237   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254   -0.5417    1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -1.4096    2.9261 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 11 32  2  0
  8  2  1  0
 31 14  1  0
 32  6  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 20 44  1  0
 21 45  1  6
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 26 50  1  0
 29 51  1  0
 30 52  1  0
 31 53  1  0
M  END

Synonyms

Value	Source
7,8-Dihydrofolate	ChEBI
7,8-Dihydrofolic acid	ChEBI
7,8-Dihydropteroylglutamate	ChEBI
Dihydrofolate	ChEBI
N-(7,8-Dihydropteroyl)-L-glutamic acid	ChEBI
7,8-Dihydropteroylglutamic acid	Generator
N-(7,8-Dihydropteroyl)-L-glutamate	Generator
7,8-Dihydro-L-folic acid	HMDB
H2PteGlu	HMDB
H2PteGlu1	HMDB
L-N-[p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acid	HMDB
N-(4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid	HMDB
N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid	HMDB
N-[4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid	HMDB
N-[4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid	HMDB
Vitamin b9	HMDB
Dihydrofolate, (D)-isomer	HMDB

Molecular Formula

C₁₉H₂₁N₇O₆

Average Mass

443.4133

Monoisotopic Mass

443.155331439

IUPAC Name

(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

Traditional Name

dihydrofolic acid

CAS Registry Number

4033-27-6

SMILES

NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1

InChI Identifier

InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1

InChI Key

OZRNSSUDZOLUSN-LBPRGKRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Pterin
Aminobenzamide
Aminobenzoic acid or derivatives
Pteridine
Benzamide
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Hydroxypyrimidine
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Amino acid
Secondary carboxylic acid amide
Ketimine
Carboxamide group
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Organoheterocyclic compound
Organic 1,3-dipolar compound
Azacycle
Organic oxygen compound
Imine
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydrofolic acids (CHEBI:15633 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	-1.8	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	2.09	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	207.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	120.99 m³·mol⁻¹	ChemAxon
Polarizability	44.31 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2469100000-dfb9d32424c0c60215dc	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-3320390000-c5791f4954b5cefa68e1	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
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-1920000000-6de8a6f7059365047fe2	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0322900000-3bd8be8b6fc531102b49	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0952200000-3a44b5c375b9b981244f	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1930000000-71775fd6210c3e719dc1	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0113900000-62b9c33c60c2e2fd46c6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xv-1349500000-3d3bae7b4497b96fc55d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9441000000-c0339a106358ca6d7221	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-0070900000-6a1481e87925b9b385e3	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-2591100000-9c973398e9038b5cdb47	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00wa-1971000000-080ecbf4dd42ca5adb42	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0089-0119700000-93e6d0f8c27c8bbe21a3	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08n9-2918500000-f3937a7ae1b8e159f6cd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-3921000000-fea748c5be0567e97935	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Lysosome
Mitochondria

Biospecimen Locations

Blood
Feces
Liver

Tissue Locations

Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192410	Dihydrofolate reductase	Enzyme	P00374	Homo sapiens
MMDBp0192469	Folylpolyglutamate synthase, mitochondrial	Enzyme	Q05932	Homo sapiens
MMDBp0193968	Thymidylate synthase	Enzyme	P04818	Homo sapiens
MMDBp0194161	Dihydrofolate reductase	Enzyme	B0YJ76	Homo sapiens
MMDBp0196796	Dihydrofolate reductase, mitochondrial	Unknown	Q86XF0

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000678	Dihydrofolic acid	Dihydrofolic acid	Not Available	Dihydrofolate Reversible Lysosomal Transport	VMH	11375437
MMDBr0000679	Dihydrofolic acid	Dihydrofolic acid	Not Available	Dihydrofolate Reversible Mitochondrial Transport	VMH	11375437
MMDBr0001217	Folic acid	Dihydrofolic acid	Dihydrofolate reductase	Folate Reductase	VMH	30371894
MMDBr0001227	Adenosine triphosphate	Pentaglutamyl Folate (Dhf)	Folylpolyglutamate synthase	Folylpolyglutamate Synthetase (Dhf)	VMH	10777604
MMDBr0001228	Adenosine triphosphate	Pentaglutamyl Folate (Dhf)	Folylpolyglutamate synthase	Folylpolyglutamate Synthetase (Dhf), Mitochondrial	VMH	10777604
MMDBr0001288	Pentaglutamyl Folate (Dhf)	Dihydrofolic acid	Gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	Gamma-Glutamyl Hydrolase (5Dhf), Extracellular	VMH	11375437 2867095 9614206
MMDBr0001289	Pentaglutamyl Folate (Dhf)	Dihydrofolic acid	Gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	Gamma-Glutamyl Hydrolase (5Dhf), Lysosomal	VMH	11375437 2867095 9614206
MMDBr0002489	Dihydrofolic acid	NAD	Dihydrofolate reductase	5, 6, 7, 8-Tetrahydrofolate:NAD+ Oxidoreductase	VMH	15153070 1631094 6882460
MMDBr0002490	Dihydrofolic acid	NADP	Dihydrofolate reductase	5, 6, 7, 8-Tetrahydrofolate:NADP+ Oxidoreductase	VMH	15153070 16171773 1631094 6882460 962851
MMDBr0002578	Dihydrofolic acid	Folic acid	Dihydrofolate reductase	Dihydrofolate:NAD+ Oxidoreductase	VMH	30371894
MMDBr0002579	Folic acid	Dihydrofolic acid	Dihydrofolate reductase	Dihydrofolate:NADP+ Oxidoreductase	VMH	30371894
MMDBr0007308	Dihydrofolic acid	Folic acid	Not Available	Dihydrofolate reductase	VMH	30371894
MMDBr0007309	Dihydrofolic acid	NADP	Not Available	Dihydrofolate Reductase	VMH	30371894
MMDBr0007310	Adenosine triphosphate	ADP	Not Available	Dihydrofolate synthase	VMH	30371894
MMDBr0007980	dUMP	Dihydrofolic acid	Not Available	Thymidylate Synthase	VMH	30371894
MMDBr0018067	NADP	Folic acid	Dihydrofolate reductase	Reduction	PathBank	31602464
MMDBr0018068	Hydrogen Ion	NADP	Dihydrofolate reductase	Reduction	PathBank	31602464
MMDBr0018069	Dihydrofolic acid	5,10-Methylene-THF	Thymidylate synthase	Synthesis	PathBank	31602464
MMDBr0018625	dUMP	Dihydrofolic acid	Thymidylate synthase	Synthesis	PathBank	31602464
MMDBr0019770	NADP	Folic acid	Dihydrofolate reductase	Reduction	PathBank	31602464
MMDBr0019771	Hydrogen Ion	NADP	Dihydrofolate reductase	Reduction	PathBank	31602464
MMDBr0019773	Dihydrofolic acid	5,10-Methylene-THF	Thymidylate synthase	Synthesis	PathBank	31602464
MMDBr0019805	dUMP	Dihydrofolic acid	Thymidylate synthase	Synthesis	PathBank	31602464

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	388	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	126	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	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.005	0.001	uM	Adult (>18 years old)	Both	Normal	HMDB	7226494
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001056

DrugBank ID

DB02015

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15633

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Navarro-Peran E, Cabezas-Herrera J, Garcia-Canovas F, Durrant MC, Thorneley RN, Rodriguez-Lopez JN: The antifolate activity of tea catechins. Cancer Res. 2005 Mar 15;65(6):2059-64. doi: 10.1158/0008-5472.CAN-04-3469. [PubMed:15781612 ]

Showing metabocard for Dihydrofolic acid (MMDBc0029538)

MOL for #<Metabolite:0x00007fe2629815b0>

3D MOL for #<Metabolite:0x00007fe2629815b0>

3D SDF for #<Metabolite:0x00007fe2629815b0>

3D-SDF for #<Metabolite:0x00007fe2629815b0>

PDB for #<Metabolite:0x00007fe2629815b0>

3D PDB for #<Metabolite:0x00007fe2629815b0>

SMILES for #<Metabolite:0x00007fe2629815b0>

INCHI for #<Metabolite:0x00007fe2629815b0>

Structure for #<Metabolite:0x00007fe2629815b0>

3D Structure for #<Metabolite:0x00007fe2629815b0>