ジヒドロ葉酸
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/12/02 02:14:22」(JST)
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Dihydrofolic acid |
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IUPAC name
N-(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
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Identifiers |
CAS number |
4033-27-6 |
PubChem |
98792 |
ChemSpider |
89228 Y |
MeSH |
dihydrofolate |
ChEBI |
CHEBI:15633 Y |
ChEMBL |
CHEMBL46294 Y |
Jmol-3D images |
Image 1 |
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O=C(O)[C@@H](NC(=O)c1ccc(cc1)NCC/2=N/C=3C(=O)\N=C(/NC=3NC\2)N)CCC(=O)O
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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 Y
Key: OZRNSSUDZOLUSN-LBPRGKRZSA-N Y
InChI=1/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
Key: OZRNSSUDZOLUSN-LBPRGKRZBB
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Properties |
Molecular formula |
C19H21N7O6 |
Molar mass |
443.414 g/mol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Dihydrofolic acid (dihydrofolate, vitamin B9) is a folic acid derivative which is converted to tetrahydrofolic acid by dihydrofolate reductase. Since tetrahydrofolate is needed to make both purines and pyrimidines, which are building blocks of DNA and RNA, dihydrofolate reductase is targeted by various drugs to prevent nucleic acid synthesis.
Interactive pathway map
Click on genes, proteins and metabolites below to link to respective articles. [1]
Fluorouracil (5-FU) Activity edit
References
- ^ The interactive pathway map can be edited at WikiPathways: "Fluoropyrimidine_Activity_WP1601". http://www.wikipathways.org/index.php/Pathway:WP1601.
Enzyme cofactors
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Active forms |
vitamins |
- TPP / ThDP (B1)
- FMN, FAD (B2)
- NAD+, NADH, NADP+, NADPH (B3)
- Coenzyme A (B5)
- PLP / P5P (B6)
- Biotin (B7)
- THFA / H4FA, DHFA / H2FA, MTHF (B9)
- AdoCbl, MeCbl (B12)
- Ascorbic Acid (C)
- Phylloquinone (K1), Menaquinone (K2)
- Coenzyme F420
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non-vitamins |
- ATP
- CTP
- SAMe
- PAPS
- GSH
- Coenzyme B
- Cofactor F430
- Coenzyme M
- Coenzyme Q
- Heme / Haem (A, B, C, O)
- Lipoic Acid
- Methanofuran
- Molybdopterin/Molybdenum cofactor
- PQQ
- THB / BH4
- THMPT / H4MPT
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minerals |
- Ca2+
- Cu2+
- Fe2+, Fe3+
- Mg2+
- Mn2+
- Mo
- Ni2+
- Se
- Zn2+
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Base forms |
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noco, nuvi, sysi/epon, met
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Vitamins (A11)
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Fat soluble |
A
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α-Carotene · β-Carotene · Retinol# · Tretinoin
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D
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D2 (Ergosterol, Ergocalciferol#) · D3 (7-Dehydrocholesterol, Previtamin D3, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol), Calcitroic acid) · D4 (Dihydroergocalciferol) · D5 · D analogues (Alfacalcidol, Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)
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E
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Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol (Alpha, Beta, Gamma, Delta) · Tocofersolan
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K
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Naphthoquinone · Phylloquinone (K1) · Menatetrenone (K2) · Menadione (K3) · Menadiol (K4)
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Water soluble |
B
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B1 (Thiamine#) · B2 (Riboflavin#) · B3 (Niacin, Nicotinamide#) · B5 (Pantothenic acid, Dexpanthenol, Pantethine) · B6 (Pyridoxine#, Pyridoxal phosphate, Pyridoxamine) · B7 (Biotin) · B9 (Folic acid, Dihydrofolic acid, Folinic acid, L-methylfolate) · B12 (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline
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C
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Ascorbic acid# · Dehydroascorbic acid
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Combinations |
Multivitamins
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco, nuvi, sysi/epon, met
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UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Role of methotrexate exposure in apoptosis and proliferation during early neurulation.
- Wang X1, Wang J, Guan T, Xiang Q, Wang M, Guan Z, Li G, Zhu Z, Xie Q, Zhang T, Niu B.
- Journal of applied toxicology : JAT.J Appl Toxicol.2014 Aug;34(8):862-9. doi: 10.1002/jat.2901. Epub 2013 Jul 9.
- Apoptosis and proliferation play important roles in embryonic development and are required for neural tube closure. The antifolate drug methotrexate (MTX) induces folate dysmetabolism by inhibition of dihydrofolate reductase and causes abnormal apoptosis and proliferation. In this study, we establis
- PMID 23836430
- Cover image, volume 35, issue 19.
- [No authors listed]
- Journal of computational chemistry.J Comput Chem.2014 Jul 15;35(19):i-ii. doi: 10.1002/jcc.23663.
- Recent studies have proposed that enzymes involve networks of coupled residues throughout the protein that participate in motions accompanying the chemical barrier crossing. On page 1411 (DOI: 10.1002/jcc.23629), Daniel Roston et al. use QM/MM simulations to reproduce experimental rates for the wild
- PMID 24920385
- Simulations of remote mutants of dihydrofolate reductase reveal the nature of a network of residues coupled to hydride transfer.
- Roston D1, Kohen A, Doron D, Major DT.
- Journal of computational chemistry.J Comput Chem.2014 Jul 15;35(19):1411-7. doi: 10.1002/jcc.23629. Epub 2014 May 2.
- Recent experimental and theoretical studies have proposed that enzymes involve networks of coupled residues throughout the protein that participate in motions accompanying chemical barrier crossing. Here, we have examined portions of a proposed network in dihydrofolate reductase (DHFR) using quantum
- PMID 24798860
Japanese Journal
- Binding Affinities and Protein Ligand Complex Geometries of Some Quinolylaryl α,β-unsaturated Ketones
- Hamlaoui Ikram,Boulfelfel Salah Eddine,Krid Adel,Bencharif Mustapha
- JOURNAL OF HEALTH SCIENCE 57(5), 397-400, 2011
- … We tested the affinities of six new compounds to bind to the catalytic site of the dihydrofolate reductase enzyme. … The binding modes of 1-aryl-(3-substitutedquinolyl)-prop-2-en-1-one analogues to the active site of the dihydrofolate reductase are investigated with ligand docking calculations. … Docking simulations indicated that these compounds have the same binding modes for dihydrofolate reductase as methotrexate. …
- NAID 130001151379
- Systematic alanine insertion reveals the essential regions that encode structure formation and activity of dihydrofolate reductase
- Shiba Rumi,Umeyama Mika,Tsukasa Sayaka,Kamikubo Hironari,Yamazaki Yoichi,Yamaguchi Mariko,Iwakura Masahiro,Kataoka Mikio
- BIOPHYSICS 7(0), 1-10, 2011
- … We applied this method to dihydrofolate reductase (DHFR), and examined the effects of alanine insertion on structure and the enzymatic activity by solubility assay and trimethoprim resistance, respectively. …
- NAID 130000406413
Related Pictures
![dihydrofolate](https://1mg.info/0/7/9/1081.jpg)
![Figure 1 - Metabolomics reveals that DHF](https://1mg.info/0/7/9/1082.jpg)
![-tetrahydrofolate) (7,8-dihydrofolate](https://1mg.info/0/7/9/1083.jpg)
![The reduction of dihydrofolate to](https://1mg.info/0/7/9/1084.jpg)
![File:Dihydrofolate reductase reaction.svg](https://1mg.info/0/7/9/1085.jpg)
★リンクテーブル★
[★]
- 英
- pteridine
- 関
- ジヒドロプテロイン酸
- |←dihydropteroate synthetase |-sulfonamides
- |+[グルタミン酸]]
- |←hidyrofolate reductase |-trimetoprim, methotrexate, pyrimethamine
[★]
- 英
- dihydrofolate, DHF
- 関
- 葉酸
[★]
- 同
- DHFR
- 同
- DHFR
- 同
- DHFR
- 同
- DHFR