dihydrofolic acid (CHEBI:15633)

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CHEBI:15633 - dihydrofolic acid

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ChEBI Name	dihydrofolic acid

ChEBI ID	CHEBI:15633

Definition	A folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division and is targeted by various drugs to prevent nucleic acid synthesis.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:14150, CHEBI:42000, CHEBI:12245, CHEBI:4564, CHEBI:20768

Supplier Information	ChemicalBook:CB8309112, eMolecules:477080, ZINC000000157526

Download	Molfile XML SDF

more structures >>

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53 55 0 0 0 0 999 V2000

-1.1520 0.2820 7.8780 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.0840 -0.2590 8.5290 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1160 -0.3600 9.8950 N 0 0 0 0 0 0 0 0 0 0 0 0

0.9740 -0.6910 7.8800 N 0 0 0 0 0 0 0 0 0 0 0 0

1.0570 -0.6130 6.5420 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0490 -1.0240 5.9580 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.0210 -0.0490 5.8140 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0070 0.0490 4.4550 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.8420 0.7700 3.8100 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8920 1.5740 4.5330 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1910 0.9240 5.8190 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.1340 0.3930 6.5200 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7850 0.8120 2.3050 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3080 -0.0400 1.8340 N 0 0 0 0 0 0 0 0 0 0 0 0

1.0550 -0.4050 -2.2430 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8470 -1.0960 -1.3220 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5980 -0.9730 0.0250 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5580 -0.1620 0.4710 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2360 0.5220 -0.4430 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0110 0.4080 -1.7920 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3200 -0.5340 -3.6890 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2280 -1.2420 -4.0800 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5550 0.1320 -4.5760 N 0 0 0 0 0 0 0 0 0 0 0 0

0.8180 0.0040 -6.0110 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.4890 0.1750 -6.7870 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4840 -0.9030 -6.3530 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.7720 -0.7350 -7.1160 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8830 0.1550 -7.9250 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.7960 -1.5740 -6.8980 O 0 0 0 0 0 0 0 0 0 0 0 0

1.7980 1.0660 -6.4390 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5520 0.8570 -7.3600 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8330 2.2440 -5.7980 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.9210 0.5940 8.3810 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6350 -0.7470 10.3700 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8890 -0.0410 10.3860 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7980 1.6190 3.9280 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5210 2.5840 4.7110 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0980 0.8730 6.1590 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7280 0.4520 1.8960 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6140 1.8370 1.9760 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8590 -0.5200 2.4720 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6540 -1.7250 -1.6670 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2090 -1.5070 0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0420 1.1500 -0.0940 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6010 0.9430 -2.5020 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1690 0.6970 -4.2640 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2370 -0.9800 -6.2180 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9080 1.1600 -6.5810 H 0 0 0 0 0 0 0 0 0 0 0 0

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-4.6230 -1.4660 -7.3880 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4620 2.9260 -6.0720 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 12 1 0 0 0 0

1 33 1 0 0 0 0

2 3 1 0 0 0 0

2 4 2 0 0 0 0

3 34 1 0 0 0 0

3 35 1 0 0 0 0

4 5 1 0 0 0 0

5 6 2 0 0 0 0

5 7 1 0 0 0 0

7 8 1 0 0 0 0

7 12 2 0 0 0 0

8 9 2 0 0 0 0

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10 37 1 0 0 0 0

11 12 1 0 0 0 0

11 38 1 0 0 0 0

13 14 1 0 0 0 0

13 39 1 0 0 0 0

13 40 1 0 0 0 0

14 18 1 0 0 0 0

14 41 1 0 0 0 0

15 16 4 0 0 0 0

15 20 4 0 0 0 0

15 21 1 0 0 0 0

16 17 4 0 0 0 0

16 42 1 0 0 0 0

17 18 4 0 0 0 0

17 43 1 0 0 0 0

18 19 4 0 0 0 0

19 20 4 0 0 0 0

19 44 1 0 0 0 0

20 45 1 0 0 0 0

21 22 2 0 0 0 0

21 23 1 0 0 0 0

23 24 1 0 0 0 0

23 46 1 0 0 0 0

24 25 1 0 0 0 0

24 30 1 0 0 0 0

24 47 1 0 0 0 0

25 26 1 0 0 0 0

25 48 1 0 0 0 0

25 49 1 0 0 0 0

26 27 1 0 0 0 0

26 50 1 0 0 0 0

26 51 1 0 0 0 0

27 28 2 0 0 0 0

27 29 1 0 0 0 0

29 52 1 0 0 0 0

30 31 2 0 0 0 0

30 32 1 0 0 0 0

32 53 1 0 0 0 0

M END): 37 ms

reading 53 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

53 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Formula

C19H21N7O6

Net Charge

Average Mass

443.41330

Monoisotopic Mass

443.15533

InChI

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

InChIKey

OZRNSSUDZOLUSN-LBPRGKRZSA-N

SMILES

Nc1nc2NCC(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=Nc2c(=O)[nH]1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via B vitamin )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. (via B vitamin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	dihydrofolic acid (CHEBI:15633) has role Escherichia coli metabolite (CHEBI:76971) dihydrofolic acid (CHEBI:15633) has role mouse metabolite (CHEBI:75771) dihydrofolic acid (CHEBI:15633) is a dihydrofolic acids (CHEBI:23743) dihydrofolic acid (CHEBI:15633) is conjugate acid of dihydrofolate(2−) (CHEBI:57451)

Incoming	dihydrofolate(2−) (CHEBI:57451) is conjugate base of dihydrofolic acid (CHEBI:15633)

IUPAC Name

N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid

Synonyms	Sources
7,8-Dihydrofolate	KEGG COMPOUND
7,8-Dihydrofolic acid	KEGG COMPOUND
7,8-Dihydropteroylglutamate	KEGG COMPOUND
Dihydrofolate	KEGG COMPOUND
Dihydrofolic acid	KEGG COMPOUND
N-(7,8-dihydropteroyl)-L-glutamic acid	ChEBI

Manual Xrefs	Databases
C00007248	KNApSAcK
C00415	KEGG COMPOUND
DB02015	DrugBank
View more database links

Registry Number	Type	Source
4033-27-6	CAS Registry Number	KEGG COMPOUND

Last Modified

05 February 2018

CHEBI:15633 - dihydrofolic acid

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