NP-MRD: Showing NP-Card for (2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid (NP0236830)

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Record Information

Version

2.0

Created at

2022-09-06 19:49:31 UTC

Updated at

2022-09-06 19:49:31 UTC

NP-MRD ID

NP0236830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

Description

5-Methyltetrahydrofolic acid belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom). THF is the immediate acceptor of one carbon units for the synthesis of thymidine-DNA, purines (RNA and DNA) and methionine. Levomefolic acid is generated by MTHFR from 5,10-methylenetetrahydrofolate (MTHF) and used to recycle homocysteine back to methionine by methionine synthase (MS). 5-Methyltetrahydrofolic acid is a moderately basic compound (based on its pKa). It bypasses several metabolic steps in the body and better binds thymidylate synthase with FdUMP, a metabolite of the drug fluorouracil. Levomefolate calcium, a calcium salt of levomefolic acid is sold under the brand name Metafolin and incorporated in Deplin. It is synthesized in the absorptive cells of the small intestine from polyglutamylated dietary folate. It is also the form found in circulation and transported across membranes into tissues and across the blood-brain barrier. (2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid is found in Capsicum annuum. In September 2012, the same three plaintiffs filed a complaint requesting that the International Trade Commission begin an 19 U.S.C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311051600062D          

 33 35  0  0  1  0            999 V2000
   -8.5737   -4.9499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -4.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -4.5374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4316   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -5.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1463   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8606   -4.9502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8606   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -6.1876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5750   -6.1877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1464   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -3.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 11 17  1  6  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  2  0  0  0  0
 21 26  1  0  0  0  0
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 27 32  2  0  0  0  0
 22 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 33  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -3.6514   -0.4021   -2.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    0.2195   -1.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5146   -0.4178   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0701    0.0082    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1673   -0.5966    1.1629 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7426   -1.6212    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8976   -2.2053    1.0853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2213   -2.0440   -0.6537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1231   -1.4631   -1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6775   -1.8898   -2.2481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4714    1.0834    1.3716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0848    1.3979    1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9622    1.4744   -0.4298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5176    1.7531   -0.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122    0.6639   -0.2701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992    0.7238   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4964   -0.3006    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8560   -0.2256   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    0.8478   -0.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477    0.9343   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2880    1.8080   -1.7602 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7064    0.0683   -0.2464 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352    0.1361   -0.4107 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8811    0.5471    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7358   -0.3067    2.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563   -1.6957    1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -2.5866    1.4949 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4482   -2.0652    2.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -1.0732   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8976   -1.9987   -1.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0200   -1.2379   -1.3317 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6129    1.8618   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2437    1.8283   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    0.0617   -2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2043   -0.3208   -3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4136   -1.4873   -1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5495   -0.2467    2.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6290   -1.5628    1.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9518   -3.2443    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9797    1.6421    2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4804    0.5606    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7755    2.3641    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253    2.2990   -0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288    2.7132   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3559    1.9834   -1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1011   -0.1769    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0120   -1.1378    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -1.0674    0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470   -0.6339    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3186    0.9691   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9597    0.6675    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5678    1.6044    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2766    0.2365    2.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571   -0.2358    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9761   -2.5529    1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4647   -1.0173   -2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397    2.7326   -1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    2.6237   -1.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 13  1  0
 13 14  1  0
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 16 17  2  0
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 13 12  1  0
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  3  9  1  0
  9 10  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  3  2  1  0
 33 16  1  0
  5  4  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 13 43  1  6
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 15 46  1  0
 17 47  1  0
 18 48  1  0
 32 57  1  0
 33 58  1  0
 22 49  1  0
 23 50  1  6
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 28 55  1  0
 31 56  1  0
 12 41  1  0
 12 42  1  0
 11 40  1  0
  7 38  1  0
  7 39  1  0
  5 37  1  0
M  END


  Mrv1652311051600062D          

 33 35  0  0  1  0            999 V2000
   -8.5737   -4.9499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  -12.1463   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.8606   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -6.1876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5750   -6.1877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1464   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -3.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
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 27 32  2  0  0  0  0
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 22 33  1  0  0  0  0
 27 28  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0236830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2

> <INCHI_IDENTIFIER>
InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m0/s1

> <INCHI_KEY>
ZNOVTXRBGFNYRX-ABLWVSNPSA-N

> <FORMULA>
C20H25N7O6

> <MOLECULAR_WEIGHT>
459.463

> <EXACT_MASS>
459.186631553

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.191147111994255

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <ALOGPS_LOGP>
-0.58

> <JCHEM_LOGP>
-1.872632241674932

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.213036453102578

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.482708448720173

> <JCHEM_PKA_STRONGEST_BASIC>
2.8308279831825462

> <JCHEM_POLAR_SURFACE_AREA>
198.48000000000002

> <JCHEM_REFRACTIVITY>
126.68129999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-NOV-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-NOV-16         0                                  
HETATM    1  N   UNK     0     -16.004  -9.240   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0     -14.671  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.671  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.337  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669  -6.160   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -9.336  -6.930   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -17.338  -8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0     -20.005  -8.470   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0     -21.339  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -21.339 -10.780   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0     -20.005 -11.550   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0     -18.672 -10.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -22.673  -8.470   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0     -24.006  -9.240   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0     -24.006 -10.780   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0     -22.673 -11.550   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0     -25.340 -11.550   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0     -22.673  -6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -20.005  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2   20                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    1   21                                                       
CONECT   21   20   26   22                                                  
CONECT   22   23   21   33                                                  
CONECT   23   24   27   22                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   21   25                                                       
CONECT   27   23   32   28                                                  
CONECT   28   27   29                                                       
CONECT   29   30   31   28                                                  
CONECT   30   29   24                                                       
CONECT   31   29                                                            
CONECT   32   27                                                            
CONECT   33   22                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
5-Methyltetrahydrofolate	Generator
5-Methyltetrahydrofolic acid	Generator
5-Methyltetrahydrofolate, (DL-glu)-isomer	MeSH
5-Methyltetrahydrofolate, (L-glu)-(R)-isomer	MeSH
5-Methyltetrahydrofolate, (L-glu)-(S)-isomer	MeSH
5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomer	MeSH
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomer	MeSH
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomer	MeSH
5-Methyltetrahydropteroylglutamate	MeSH
CH3-FH4	MeSH
L-Methyl folate	MeSH
N(5)-Methyltetrahydrofolic acid	MeSH
Mefolinate	MeSH
Methyl folate	MeSH
(2S)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,2,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate	Generator

Chemical Formula

C₂₀H₂₅N₇O₆

Average Mass

459.4630 Da

Monoisotopic Mass

459.18663 Da

IUPAC Name

(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

Traditional Name

(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

CAS Registry Number

Not Available

SMILES

CN1C(CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2

InChI Identifier

InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m0/s1

InChI Key

ZNOVTXRBGFNYRX-ABLWVSNPSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Capsicum annuum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Not Available

Direct Parent

Benzoxazines

Alternative Parents

Substituents

Benzoxazine
N-methylpyrrole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Thiocarbamic acid ester
Thiocarbamic acid derivative
Oxacycle
Nitrile
Carbonitrile
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.58	ALOGPS
logP	-1.9	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	2.83	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	198.48 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.68 m³·mol⁻¹	ChemAxon
Polarizability	46.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB04789

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007252

Chemspider ID

Not Available

KEGG Compound ID

C00440

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levomefolic acid

METLIN ID

Not Available

PubChem Compound

9825434

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid (NP0236830)

MOL for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D MOL for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D SDF for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D-SDF for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

PDB for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D PDB for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

SMILES for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

INCHI for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

Structure for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D Structure for NP0236830 ((2s)-2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)