NP-MRD: Showing NP-Card for (2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid (NP0305359)

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Record Information

Version

2.0

Created at

2022-09-10 21:07:50 UTC

Updated at

2022-09-10 21:07:50 UTC

NP-MRD ID

NP0305359

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Leucovorin, also known as folinate or folinic acid, 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. A formyltetrahydrofolic acid in which the formyl group is located at position 5. Leucovorin is a drug which is used for the treatment of osteosarcoma (after high dose methotrexate therapy). Used to diminish the toxicity and counteract the effects of impaired methotrexate elimination and of inadvertent overdosages of folic acid antagonists, and to treat megaloblastic anemias due to folic acid deficiency. Also used in combination with 5-fluorouracil to prolong survival in the palliative treatment of patients with advanced colorectal cancer. Leucovorin is a moderately basic compound (based on its pKa). (2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid is found in Capsicum annuum and Mus musculus. In humans, leucovorin is involved in the metabolic disorder called the methylenetetrahydrofolate reductase deficiency (mthfrd) pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306071917182D          

 34 36  0  0  0  0            999 V2000
 9994.7996 9998.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5147 9998.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2279 9997.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9431 9997.2190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8040 9998.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5184 9998.4567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.2349 9998.8697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.9493 9998.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6657 9998.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3822 9998.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0965 9998.8697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.3822 9997.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2349 9999.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.949310000.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.518410000.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8040 9999.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3711 9998.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9428 9995.9729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0887 9998.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3745 9998.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6600 9998.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6600 9997.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3744 9997.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0888 9997.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3712 9997.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6569 9997.2154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6569 9996.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3712 9995.9781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0856 9996.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0856 9997.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8000 9995.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5142 9996.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5143 9997.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7999 9997.6278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 19  1  0  0  0  0
  4 22  1  0  0  0  0
 19  5  1  0  0  0  0
 25 30  1  0  0  0  0
 29 30  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  1  0  0  0  0
 31 32  1  0  0  0  0
 29 31  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 34  1  0  0  0  0
 33  3  1  0  0  0  0
 27 18  1  0  0  0  0
 25 17  2  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -9.8217    0.8972    1.1830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4147    0.9991    1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7476    1.9378    1.7817 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4060    2.0060    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7209    2.8488    2.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7476    1.1209    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4568    0.1511    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7849    0.1155    0.2494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6999   -0.7150   -0.7149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2671   -0.7078   -0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -0.1409    0.4647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1828    0.0483    0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5898   -1.2423    0.0928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044   -1.3763   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -0.2827    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -0.4431   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968   -1.6421   -0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0315   -1.8346   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4314   -2.9545   -0.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9295   -0.7973   -0.1559 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3670   -0.9194   -0.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9309   -0.0641   -1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6984    1.3875   -1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1894    2.1574   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8285    1.6492    0.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9654    3.5431   -0.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0677   -0.9636    1.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857   -0.7866    2.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4523   -1.2173    1.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7412   -2.7429   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -2.5911   -0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3466    1.1570    0.6462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6623    2.3723    0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2053    3.4899    0.5696 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4159    1.5137    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2530    0.2149    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3218   -0.6038   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2548   -1.4150   -1.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996   -0.0850   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866   -1.7327   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9540   -0.7879    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740    0.4396    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9426    0.7797   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -2.1073    0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2306    0.7104    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    0.4475    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571    0.0976    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5093   -1.9991   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6726   -0.5222   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0586   -0.2109   -1.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1962    1.8183   -2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    1.6646   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4585    4.0652   -0.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8198   -1.9732    0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -3.7100   -0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2491   -3.4840   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    2.4197    0.5885 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  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 30  1  0
 30 31  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 26  1  0
 24 25  2  0
 21 27  1  0
 27 29  1  0
 27 28  2  0
 11 32  1  0
 32 33  1  0
 33 34  2  0
  7  8  1  0
  8  2  1  0
 32  6  1  0
 31 14  1  0
  1 35  1  0
  1 36  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  1
 12 42  1  0
 12 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 30 55  1  0
 31 56  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 26 53  1  0
 29 54  1  0
 33 57  1  0
  8 37  1  0
M  END


  Mrv1652306071917182D          

 34 36  0  0  0  0            999 V2000
 9994.7996 9998.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5147 9998.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2279 9997.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9431 9997.2190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8040 9998.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5184 9998.4567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.2349 9998.8697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.9493 9998.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6657 9998.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3822 9998.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0965 9998.8697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.3822 9997.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2349 9999.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.949310000.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.518410000.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8040 9999.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3711 9998.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9428 9995.9729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0887 9998.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3745 9998.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6600 9998.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6600 9997.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3744 9997.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0888 9997.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3712 9997.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6569 9997.2154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6569 9996.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3712 9995.9781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0856 9996.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0856 9997.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8000 9995.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5142 9996.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5143 9997.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7999 9997.6278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 19  1  0  0  0  0
  4 22  1  0  0  0  0
 19  5  1  0  0  0  0
 25 30  1  0  0  0  0
 29 30  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  1  0  0  0  0
 31 32  1  0  0  0  0
 29 31  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 34  1  0  0  0  0
 33  3  1  0  0  0  0
 27 18  1  0  0  0  0
 25 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0305359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2C=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m0/s1

> <INCHI_KEY>
VVIAGPKUTFNRDU-ABLWVSNPSA-N

> <FORMULA>
C20H23N7O7

> <MOLECULAR_WEIGHT>
473.446

> <EXACT_MASS>
473.165896109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.34154214681111

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.06

> <JCHEM_LOGP>
-2.6744360693430935

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.2084919432830645

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4734158052231012

> <JCHEM_PKA_STRONGEST_BASIC>
2.807468599105256

> <JCHEM_POLAR_SURFACE_AREA>
215.55

> <JCHEM_REFRACTIVITY>
126.46200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
folinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUN-19         0                                  
HETATM    1  C   UNK     0    8656.9598663.794   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8658.2948664.561   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8659.6258662.244   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8660.9618661.475   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8666.3018664.557   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8667.6348663.786   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8668.9728664.557   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.3058663.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8671.6438664.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.9808663.786   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8674.3148664.557   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8672.9808662.244   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8668.9728666.098   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8670.3058666.869   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8667.6348666.869   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8666.3018666.098   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8654.2938663.794   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0    8651.6278659.149   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    8664.9668663.785   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8663.6328664.555   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8662.2998663.785   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8662.2998662.246   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8663.6328661.476   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8664.9668662.246   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8654.2938662.239   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0    8652.9608661.469   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0    8652.9608659.929   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0    8654.2938659.159   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0    8655.6268659.929   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8655.6268661.469   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0    8656.9608659.159   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0    8658.2938659.929   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8658.2938661.469   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0    8656.9608662.239   0.000  0.00  0.00           N+0
CONECT    1    2   34                                                       
CONECT    2    1                                                            
CONECT    3    4   33                                                       
CONECT    4    3   22                                                       
CONECT    5    6   16   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5                                                            
CONECT   17   25                                                            
CONECT   18   27                                                            
CONECT   19   20   24    5                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23    4                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   30   26   17                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   18                                                  
CONECT   28   27   29                                                       
CONECT   29   30   31   28                                                  
CONECT   30   25   29   34                                                  
CONECT   31   32   29                                                       
CONECT   32   33   31                                                       
CONECT   33   32   34    3                                                  
CONECT   34   33   30    1                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(5-Formyl-5,6,7,8-tetrahydropteroyl)glutamate	ChEBI
10-Formyl-7,8-dihydrofolic acid	ChEBI
5-Formyl-5,6,7,8-tetrahydrofolic acid	ChEBI
5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid	ChEBI
5-Formyltetrahydrofolate	ChEBI
Acide folinique	ChEBI
Folinate	ChEBI
Folinic acid	ChEBI
L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid	ChEBI
Leucovorinum	ChEBI
N-(5-Formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid	ChEBI
N5-Formyl-5,6,7,8-tetrahydrofolic acid	ChEBI
N5-Formyltetrahydrofolic acid	ChEBI
(5-Formyl-5,6,7,8-tetrahydropteroyl)glutamic acid	Generator
10-Formyl-7,8-dihydrofolate	Generator
5-Formyl-5,6,7,8-tetrahydrofolate	Generator
5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamate	Generator
5-Formyltetrahydrofolic acid	Generator
L(-)-5-Formyl-5,6,7,8-tetrahydrofolate	Generator
N-(5-Formyl-5,6,7,8-tetrahydropteroyl)-L-glutamate	Generator
N5-Formyl-5,6,7,8-tetrahydrofolate	Generator
N5-Formyltetrahydrofolate	Generator
Leucovorin	ChEBI
(2S)-2-[[4-[(2-amino-5-Formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioate	Generator
5-Formyltetrahydropteroylglutamate	MeSH
Calcium folinate	MeSH
Leucovorin, calcium (1:1) salt, (DL)-isomer	MeSH
Wellcovorin	MeSH
Acid, folinic	MeSH
Leukovorum	MeSH
Monosodium salt leucovorin	MeSH
5 Formyltetrahydropteroylglutamate	MeSH
Calcium leucovorin	MeSH
Folinate, calcium	MeSH
Folinic acid SF	MeSH
Leucovorin, calcium (1:1) salt	MeSH
Leucovorin, calcium (1:1) salt, pentahydrate	MeSH
Factor, citrovorum	MeSH
N(5)-Formyltetrahydrofolate	MeSH
Citrovorum factor	MeSH
Leucovorin, calcium	MeSH
Leukovorin	MeSH
Leucovorin, (R)-isomer	MeSH
5 Formyltetrahydrofolate	MeSH
Leucovorin, (DL)-isomer	MeSH
Folinic acid-SF	MeSH
Leucovorin, monosodium salt	MeSH
(6R,S)-5-Formyltetrahydrofolate	HMDB
5-Formyltetrahydropteroylglutamic acid	HMDB
CF	HMDB
Kunyrin	HMDB
Leucoverin	HMDB
N5-Formyl-THF	HMDB
Welcovorin	HMDB
l-Leucovorin	HMDB

Chemical Formula

C₂₀H₂₃N₇O₇

Average Mass

473.4460 Da

Monoisotopic Mass

473.16590 Da

IUPAC Name

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

Traditional Name

folinic acid

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2C=O)N1

InChI Identifier

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m0/s1

InChI Key

VVIAGPKUTFNRDU-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
Mus musculus	LOTUS Database	35616633

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
Secondary aliphatic/aromatic amine
Hydroxypyrimidine
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Organoheterocyclic compound
Secondary amine
Azacycle
Carboxylic acid
Organic oxygen compound
Carbonyl group
Amine
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

formyltetrahydrofolic acid (CHEBI:15640 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-2.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	2.81	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	215.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.46 m³·mol⁻¹	ChemAxon
Polarizability	46.34 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

DB00650

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Folinic_acid

METLIN ID

Not Available

PubChem Compound

6006

PDB ID

Not Available

ChEBI ID

15640

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid (NP0305359)

MOL for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D MOL for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D SDF for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D-SDF for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

PDB for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D PDB for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

SMILES for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

INCHI for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

Structure for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)

3D Structure for NP0305359 ((2s)-2-[(4-{[(5-formyl-4-hydroxy-2-imino-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid)