Compound

(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate

CHEBI:15636ChEBI

Structure

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A generated conformer of (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C20H21N7O6
Mass: 455.431 g/mol
Charge: -2
InChIKey: QYNUQALWYRSVHF-OLZOCXBDSA-L
SMILES: [H][C@]12CNc3nc(N)nc(=O)c3N1CN(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

17 statements

17 statements · 2 reference databases · Subject: (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate · Sources: Rhea, UniProt

Order

(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is converted to (6R)-5,10-methenyltetrahydrofolateCompoundRhea RHEA:22812Inferred 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
(6S)-5-methyl-5,6,7,8-tetrahydrofolate is converted to (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateCompoundRhea RHEA:19821Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is converted to (6S)-5-methyl-5,6,7,8-tetrahydrofolateCompoundRhea RHEA:19821Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is converted to (6S)-5-methyl-5,6,7,8-tetrahydrofolateCompoundRhea RHEA:19817Inferred only
CRY1 requires the cofactor (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateProteinUniProt Q16526Inferred only
CRY2 requires the cofactor (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateProteinUniProt Q49AN0Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of AMTProteinRhea RHEA:16945Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of MTHFD1ProteinRhea RHEA:22812Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of MTHFD2ProteinRhea RHEA:22892Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of MTHFD2LProteinRhea RHEA:22812Inferred only

Show the remaining 5

(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of MTHFD2LProteinRhea RHEA:22892Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of MTHFRProteinRhea RHEA:19817Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of SHMT1ProteinRhea RHEA:15481Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of SHMT2ProteinRhea RHEA:15481Inferred only
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate is a substrate of TYMSProteinRhea RHEA:12104Inferred only

Reactions

22 reactions

(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+D-alanine+waterCHEBI:58275+(6S)-5,6,7,8-tetrahydrofolate
Reaction pageDirection not assertedBalanced
Rhea RHEA:10064CC BY 4.0Reference data
dCMP+(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+waterCHEBI:57962+(6S)-5,6,7,8-tetrahydrofolate
Reaction pageDirection not assertedBalanced
Rhea RHEA:11280CC BY 4.0Reference data
dCMP+(6R)-5,10-methylene-5,6,7,8-tetrahydrofolateCHEBI:57886+7,8-dihydrofolate
Reaction pageDirection not assertedBalanced
Rhea RHEA:11568CC BY 4.0Reference data
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+3-methyl-2-oxobutanoate+waterCHEBI:11561+(6S)-5,6,7,8-tetrahydrofolate
Reaction pageDirection not assertedBalanced
Rhea RHEA:11824CC BY 4.0Reference data
dUMP+(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate7,8-dihydrofolate+dTMP
Catalysed by TYMS
Reaction pageLeft to rightBalanced
Rhea RHEA:12104CC BY 4.0Reference data
(6S)-5-methyl-5,6,7,8-tetrahydrofolate+2oxidized [2Fe-2S]-[ferredoxin](6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+2reduced [2Fe-2S]-[ferredoxin]+2hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:14229CC BY 4.0Reference data
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+glycine+water(6S)-5,6,7,8-tetrahydrofolate+L-seryl residue
Catalysed by SHMT1 or SHMT2
Reaction pageReversibleBalanced
Rhea RHEA:15481CC BY 4.0Reference data
CHEBI:65315+(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+NADH(2-)+hydronCHEBI:74447+(6S)-5,6,7,8-tetrahydrofolate+NAD(1-)
Reaction pageDirection not assertedBalanced
Rhea RHEA:16873CC BY 4.0Reference data
N(6)-[(R)-S(8)-aminomethyldihydrolipoyl]-L-lysyl-[protein]+(6S)-5,6,7,8-tetrahydrofolateN(6)-[(R)-dihydrolipoyl]-L-lysyl-[protein]+(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+ammonium
Catalysed by AMT
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:16945CC BY 4.0Reference data
(6S)-5-methyl-5,6,7,8-tetrahydrofolate+NADP(3-)(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+NADPH(4-)+hydron
Catalysed by MTHFR
Reaction pageRight to leftBalanced
Rhea RHEA:19817CC BY 4.0Reference data
(6S)-5-methyl-5,6,7,8-tetrahydrofolate+NAD(1-)(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+NADH(2-)+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:19821CC BY 4.0Reference data
(6R)-5,10-methylene-5,6,7,8-tetrahydrofolate+NADP(3-)(6R)-5,10-methenyltetrahydrofolate+NADPH(4-)
Catalysed by MTHFD1 or MTHFD2L
Reaction pageLeft to rightBalanced
Rhea RHEA:22812CC BY 4.0Reference data

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Other names

3 names

Resolves to: (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate

Also called: (6R)-5,10-CH2-H4folateN-(5,10-methylene-5,6,7,8-tetrahydropteroyl)-L-glutamate
Systematic name: N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl]benzoyl}-L-glutamate