Compound

(6R)-5,10-methenyltetrahydrofolate

A dicarboxylic acid anion arising from deprotonation of both carboxylic acid functions of (6R)-5,10-methenyltetrahydrofolic acid.

Definition from ChEBI (CHEBI:57455), read 2026-09-23. CC BY 4.0.

CHEBI:57455ChEBI

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Structure

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A generated conformer of (6R)-5,10-methenyltetrahydrofolate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C20H20N7O6
Mass: 454.423 g/mol
Charge: -1
InChIKey: MEANFMOQMXYMCT-OLZOCXBDSA-M
SMILES: [H][C@]12CNc3nc(N)nc(=O)c3[N+]1=CN(c1ccc(C(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-])cc1)C2
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

8 entities

8 entities reached.

0 reported hops8 assembled from the scaffold

What the reference databases state

Statements

40 statements

40 statements · 2 reference databases · Subject: (6R)-5,10-methenyltetrahydrofolate · Sources: Human-GEM, Rhea

Order

(6R)-10-formyltetrahydrofolate is converted to (6R)-5,10-methenyltetrahydrofolateCompoundRhea RHEA:23700Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to (6R)-10-formyltetrahydrofolateCompoundRhea RHEA:23700Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is converted to (6R)-5,10-methenyltetrahydrofolateCompoundRhea RHEA:22892Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateCompoundRhea RHEA:22892Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is converted to (6R)-5,10-methenyltetrahydrofolateCompoundRhea RHEA:22812Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to (6R)-5,10-methylenetetrahydrofolic acidCompoundHuman-GEM MAR08144Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to (6R)-5,10-methylenetetrahydrofolic acidCompoundHuman-GEM MAR04444Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to (6R)-5,10-methylenetetrahydrofolic acidCompoundHuman-GEM MAR04442Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to (6R)-5,10-methylenetetrahydrofolic acidCompoundHuman-GEM MAR04440Inferred only
(6R)-5,10-methylenetetrahydrofolic acid is converted to (6R)-5,10-methenyltetrahydrofolateCompoundHuman-GEM MAR04440Inferred only
(6R)-5,10-methylenetetrahydrofolic acid is converted to (6R)-5,10-methenyltetrahydrofolateCompoundHuman-GEM MAR04442Inferred only
(6R)-5,10-methylenetetrahydrofolic acid is converted to (6R)-5,10-methenyltetrahydrofolateCompoundHuman-GEM MAR04444Inferred only

Show the remaining 28

(6R)-5,10-methylenetetrahydrofolic acid is converted to (6R)-5,10-methenyltetrahydrofolateCompoundHuman-GEM MAR08144Inferred only
10-formyltetrahydrofolic acid is converted to (6R)-5,10-methenyltetrahydrofolateCompoundHuman-GEM MAR04505Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to 10-formyltetrahydrofolic acidCompoundHuman-GEM MAR04505Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to 10-formyltetrahydrofolic acidCompoundHuman-GEM MAR04503Inferred only
10-formyltetrahydrofolic acid is converted to (6R)-5,10-methenyltetrahydrofolateCompoundHuman-GEM MAR04503Inferred only
5-formimidoyltetrahydrofolate is converted to (6R)-5,10-methenyltetrahydrofolateCompoundHuman-GEM MAR03929Inferred only
5-formimidoyltetrahydrofolate is converted to (6R)-5,10-methenyltetrahydrofolateCompoundRhea RHEA:22736Inferred only
(6R)-5,10-methenyltetrahydrofolate is converted to 5-formimidoyltetrahydrofolateCompoundHuman-GEM MAR03929Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of FTCDProteinHuman-GEM MAR03929Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD1ProteinHuman-GEM MAR04444Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD1ProteinHuman-GEM MAR04442Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD1ProteinRhea RHEA:23700Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD1ProteinHuman-GEM MAR08144Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD1ProteinHuman-GEM MAR04503Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD1LProteinHuman-GEM MAR04505Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD1LProteinHuman-GEM MAR04444Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2ProteinHuman-GEM MAR04505Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2ProteinHuman-GEM MAR04444Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2ProteinRhea RHEA:22892Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2ProteinHuman-GEM MAR04440Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2ProteinRhea RHEA:23700Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2LProteinHuman-GEM MAR04505Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2LProteinRhea RHEA:22892Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2LProteinRhea RHEA:23700Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFD2LProteinHuman-GEM MAR04440Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of MTHFSProteinRhea RHEA:10488Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of SHMT1ProteinRhea RHEA:34767Inferred only
(6R)-5,10-methenyltetrahydrofolate is a substrate of SHMT2ProteinHuman-GEM MAR04665Inferred only

Reactions

17 reactions

(6R)-5,10-methenyltetrahydrofolate+ammonium5-formimidoyltetrahydrofolate+proton
Catalysed by FTCD
Reaction pageReversibleBalancedEC 4.3.1.4cytosol
Human-GEM MAR03929CC BY 4.0Reference data
(6R)-5,10-methenyltetrahydrofolate+NADH(2-)(6R)-5,10-methylenetetrahydrofolic acid+NAD(+)
Catalysed by MTHFD2 or MTHFD2L
Reaction pageReversibleBalancedEC 1.5.1.15mitochondrial matrix
Human-GEM MAR04440CC BY 4.0Reference data
(6R)-5,10-methenyltetrahydrofolate+NADPH(4-)(6R)-5,10-methylenetetrahydrofolic acid+NADP(3-)
Catalysed by MTHFD1
Reaction pageReversibleBalancedEC 1.5.1.5cytosol
Human-GEM MAR04442CC BY 4.0Reference data
(6R)-5,10-methenyltetrahydrofolate+NADPH(4-)(6R)-5,10-methylenetetrahydrofolic acid+NADP(3-)
Catalysed by MTHFD2 or MTHFD1 or MTHFD1L
Reaction pageReversibleBalancedEC 1.5.1.5mitochondrial matrix
Human-GEM MAR04444CC BY 4.0Reference data
10-formyltetrahydrofolic acid+proton(6R)-5,10-methenyltetrahydrofolate+water
Catalysed by MTHFD1
Reaction pageReversibleBalancedEC 3.5.4.9cytosol
Human-GEM MAR04503CC BY 4.0Reference data
10-formyltetrahydrofolic acid+proton(6R)-5,10-methenyltetrahydrofolate+water
Catalysed by MTHFD2 or MTHFD1L or MTHFD2L
Reaction pageReversibleBalancedEC 3.5.4.9mitochondrial matrix
Human-GEM MAR04505CC BY 4.0Reference data
(6R)-5,10-methenyltetrahydrofolate+waterMAM01100m+proton
Catalysed by SHMT2
Reaction pageLeft to rightBalancedEC 2.1.2.10mitochondrial matrix
Human-GEM MAR04665CC BY 4.0Reference data
MAM01100m+ATP(6R)-5,10-methenyltetrahydrofolate+ADP+phosphate(3-)
Catalysed by MTHFS
Reaction pageLeft to rightBalancedEC 6.3.3.2mitochondrial matrix
Human-GEM MAR04666CC BY 4.0Reference data
MAM01100c+ATP(6R)-5,10-methenyltetrahydrofolate+ADP+phosphate(3-)
Catalysed by MTHFS
Reaction pageLeft to rightBalancedEC 6.3.3.2cytosol
Human-GEM MAR08143CC BY 4.0Reference data
(6R)-5,10-methenyltetrahydrofolate+NADH(2-)(6R)-5,10-methylenetetrahydrofolic acid+NAD(+)
Catalysed by MTHFD1
Reaction pageReversibleBalancedEC 1.5.1.5cytosol
Human-GEM MAR08144CC BY 4.0Reference data
CHEBI:57457+ATP(4-)(6R)-5,10-methenyltetrahydrofolate+ADP(3-)+hydrogenphosphate
Catalysed by MTHFS
Reaction pageDirection not assertedBalanced
Rhea RHEA:10488CC BY 4.0Reference data
5-formimidoyltetrahydrofolate+2hydron(6R)-5,10-methenyltetrahydrofolate+ammonium
Catalysed by FTCD
Reaction pageLeft to rightBalanced
Rhea RHEA:22736CC BY 4.0Reference data

Show the remaining 5

Other names

1 name

Resolves to: (6R)-5,10-methenyltetrahydrofolate

Systematic name: N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl]benzoyl}-L-glutamate