Cannabis Compound Database: Showing Compound Card for 10-Formyltetrahydrofolate (CDB005118)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (10)transporters (2) Show 13 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:11:07 UTC

Updated at

2020-11-18 16:39:24 UTC

CannabisDB ID

CDB005118

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

10-Formyltetrahydrofolate

Description

10-Formyltetrahydrofolate, also known as 10-formyl-THF or 10-formyl-H4pteglu1, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. ightleftharpoons } CH2H2F + NADH + H+In the second step 5,10-methenyltetrahydrofolate undergoes hydrolysis:CH2H2F + H2O ⇌ {\displaystyle. 10-Formyltetrahydrofolate is a strong basic compound (based on its pKa). 10-Formyltetrahydrofolate exists in all eukaryotes, ranging from yeast to humans. Within humans, 10-formyltetrahydrofolate participates in a number of enzymatic reactions. In particular, 10-formyltetrahydrofolate and glycineamideribotide can be converted into tetrahydrofolic acid and 5'-phosphoribosyl-N-formylglycinamide through the action of the enzyme trifunctional purine biosynthetic protein adenosine-3. In addition, 10-formyltetrahydrofolate and AICAR can be converted into tetrahydrofolic acid and phosphoribosyl formamidocarboxamide; which is catalyzed by the enzyme bifunctional purine biosynthesis protein purh. In these reactions 10-CHO-THF is used as a substrate in formyltransferase reactions. In humans, 10-formyltetrahydrofolate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Outside of the human body, 10-Formyltetrahydrofolate has been detected, but not quantified in, several different foods, such as breadfruits, catjang pea, climbing beans, kai-lans, and pears. This could make 10-formyltetrahydrofolate a potential biomarker for the consumption of these foods. 10-CHO-THF is required for the formylation of methionyl-tRNA formyltransferase to give fMet-tRNA.10-CHO-THF is produced from methylenetetrahydrofolate (CH2H4F) via a two step process. Two equivalents of 10-CHO-THF are required in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase. ightleftharpoons } 10-formyltetrahydrofolate10-CHO-THF is also produced by the reactionATP + formate + tetrahydrofolate ⇌ {\displaystyle. 10-Formyltetrahydrofolate (10-CHO-THF) is a form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. It can be converted back into tetrahydrofolate (THF) by formyltetrahydrofolate dehydrogenase or THF and formate by formyltetrahydrofolate deformylase. ightleftharpoons } ADP + phosphate + 10-formyltetrahydrofolateThis reaction is catalyzed by formate-tetrahydrofolate ligase. 10-Formyltetrahydrofolate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
10-Formyl-THF	Kegg
10-Formyltetrahydrofolic acid	Generator
10-Formyl-(6Rs)-tetrahydrofolic acid	HMDB
10-Formyl-H4pteglu1	HMDB
10-Formyl-tetrahydrofolate	HMDB
10-Formyltetrahydropteroylglutamate	HMDB
10-Formyltetrahydropteroylglutamic acid	HMDB
10-FTHF	HMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamate	HMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamic acid	HMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-glutamate	HMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-glutamic acid	HMDB
N10-Formyl-5,6,7,8-tetrahydrofolate	HMDB
N10-Formyl-5,6,7,8-tetrahydrofolic acid	HMDB
N10-Formyl-H4F	HMDB
N10-Formyl-THF	HMDB
N10-Formyltetrahydrofolate	HMDB
N10-Formyltetrahydrofolic acid	HMDB
N10-Formyltetrahydropteroylglutamate	HMDB

Chemical Formula

C₂₀H₂₃N₇O₇

Average Molecular Weight

473.44

Monoisotopic Molecular Weight

473.1659

IUPAC Name

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

Traditional Name

(2S)-2-[(4-{N-[(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid

CAS Registry Number

2800-34-2

SMILES

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

InChI Identifier

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1

InChI Key

AUFGTPPARQZWDO-YUZLPWPTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Tetrahydrofolic acids

Alternative Parents

Substituents

Tetrahydrofolic acid
Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
Acylaminobenzoic acid or derivatives
Alpha-amino acid or derivatives
Anilide
Benzoic acid or derivatives
Benzamide
Benzoyl
Pyrimidone
Aminopyrimidine
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Carboxylic acid derivative
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Cell and elements:

Extracellular

Subcellular:

Physical Properties

State

Solid

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	-1.5	ALOGPS
logP	-4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	216.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	135.7 m³·mol⁻¹	ChemAxon
Polarizability	46.38 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

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	10-Formyltetrahydrofolate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-2733900000-d416b73a1673d1220b87	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0v4i-2913374000-7b894dbf7f83fe5cd9d7	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolate, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05cr-0401900000-21104c38dc03ca4e7a0e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-0935700000-2f12524764eca10dcf15	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0910000000-03f41886e7967d0201eb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-1244cea99701ed75f41c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bc-1123900000-cdcadc51a3f47cb93886	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9842000000-62efadef6701421ce2c5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0002900000-e6e9d4109ecb3ef0bbee	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1729400000-02f5fdbf97e3ce7a3a95	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-0932000000-68bdb6e09b80b22288c6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-19d839ffa3d1b1988450	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0200900000-93ad732aff1ff91aa085	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0v03-4920300000-17e6f1c09b0e093800ef	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Folate Metabolism
Methotrexate Action Pathway		Not Available
Folate malabsorption, hereditary		Not Available
Purine Metabolism
Adenosine Deaminase Deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Trifunctional purine biosynthetic protein adenosine-3	GART	21q22.11	P22102	details
Bifunctional purine biosynthesis protein PURH	ATIC	2q35	P31939	details
Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial	MTHFD2	2p13.1	P13995	details
C-1-tetrahydrofolate synthase, cytoplasmic	MTHFD1	14q24	P11586	details
Cytosolic 10-formyltetrahydrofolate dehydrogenase	ALDH1L1	3q21.3	O75891	details
Probable bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase 2	MTHFD2L	4q13.3	Q9H903	details
Mitochondrial 10-formyltetrahydrofolate dehydrogenase	ALDH1L2	12q23.3	Q3SY69	details
Methionyl-tRNA formyltransferase, mitochondrial	MTFMT	15q22.31	Q96DP5	details
Monofunctional C1-tetrahydrofolate synthase, mitochondrial	MTHFD1L	6q25.1	Q6UB35	details
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	MTHFD2	2p13.1	Q7Z650	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cytosolic 10-formyltetrahydrofolate dehydrogenase	ALDH1L1	3q21.3	O75891	details
Mitochondrial 10-formyltetrahydrofolate dehydrogenase	ALDH1L2	12q23.3	Q3SY69	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Trifunctional purine biosynthetic protein adenosine-3	GART	21q22.11	P22102	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000972

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030256

KNApSAcK ID

Not Available

Chemspider ID

109092

KEGG Compound ID

C00234

BioCyc ID

Not Available

BiGG ID

34337

Wikipedia Link

10-Formyltetrahydrofolate

METLIN ID

5912

PubChem Compound

122347

PDB ID

Not Available

ChEBI ID

15637

References

General References

Not Available

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details

1. Trifunctional purine biosynthetic protein adenosine-3

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: GART
Uniprot ID:: P22102
Molecular weight:: 107766.295

Enzyme Details

2. Bifunctional purine biosynthesis protein PURH

General function:: Involved in IMP cyclohydrolase activity
Specific function:: Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:: ATIC
Uniprot ID:: P31939
Molecular weight:: 64615.255

Enzyme Details

3. Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: MTHFD2
Uniprot ID:: P13995
Molecular weight:: 37894.775

Enzyme Details

4. C-1-tetrahydrofolate synthase, cytoplasmic

General function:: Involved in formate-tetrahydrofolate ligase activity
Specific function:: Not Available
Gene Name:: MTHFD1
Uniprot ID:: P11586
Molecular weight:: 101530.36

Enzyme Details

5. Cytosolic 10-formyltetrahydrofolate dehydrogenase

General function:: Involved in formyltetrahydrofolate dehydrogenase activity
Specific function:: Not Available
Gene Name:: ALDH1L1
Uniprot ID:: O75891
Molecular weight:: 99752.535

Enzyme Details

6. Probable bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase 2

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: MTHFD2L
Uniprot ID:: Q9H903
Molecular weight:: 37315.11

Enzyme Details

7. Mitochondrial 10-formyltetrahydrofolate dehydrogenase

General function:: Involved in formyltetrahydrofolate dehydrogenase activity
Specific function:: Not Available
Gene Name:: ALDH1L2
Uniprot ID:: Q3SY69
Molecular weight:: 101744.98

Enzyme Details

8. Methionyl-tRNA formyltransferase, mitochondrial

General function:: Involved in methionyl-tRNA formyltransferase activity
Specific function:: Formylates methionyl-tRNA in mitochondria. A single tRNA(Met) gene gives rise to both an initiator and an elongator species via an unknown mechanism (By similarity).
Gene Name:: MTFMT
Uniprot ID:: Q96DP5
Molecular weight:: 43831.73

Enzyme Details

9. Monofunctional C1-tetrahydrofolate synthase, mitochondrial

General function:: Involved in formate-tetrahydrofolate ligase activity
Specific function:: May provide the missing metabolic reaction required to link the mitochondria and the cytoplasm in the mammalian model of one-carbon folate metabolism in embryonic an transformed cells complementing thus the enzymatic activities of MTHFD2 (By similarity).
Gene Name:: MTHFD1L
Uniprot ID:: Q6UB35
Molecular weight:: 105888.19

Enzyme Details

10. Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: MTHFD2
Uniprot ID:: Q7Z650
Molecular weight:: 26849.1

Transporters

Enzyme Details

1. Cytosolic 10-formyltetrahydrofolate dehydrogenase

General function:: Involved in formyltetrahydrofolate dehydrogenase activity
Specific function:: Not Available
Gene Name:: ALDH1L1
Uniprot ID:: O75891
Molecular weight:: 99752.535

Enzyme Details

2. Mitochondrial 10-formyltetrahydrofolate dehydrogenase

General function:: Involved in formyltetrahydrofolate dehydrogenase activity
Specific function:: Not Available
Gene Name:: ALDH1L2
Uniprot ID:: Q3SY69
Molecular weight:: 101744.98

Only showing the first 10 proteins. There are 13 proteins in total.

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Showing Compound Card for 10-Formyltetrahydrofolate (CDB005118)

Structure for CDB005118 (10-Formyltetrahydrofolate)

Enzymes

Transporters