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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:06 UTC
Update Date2019-07-23 07:14:15 UTC
HMDB IDHMDB0060403
Secondary Accession Numbers
  • HMDB60403
Metabolite Identification
Common Name5,6,7,8-Tetrahydromethanopterin
Description5,6,7,8-Tetrahydromethanopterin, also known as H4MPT, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. These are lipids containing a glycosyl moiety (one or several units) linked to the hydroxyl group of a fatty alcohol. 5,6,7,8-Tetrahydromethanopterin is an extremely strong basic compound (based on its pKa). 5,6,7,8-Tetrahydromethanopterin exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1563866055
Synonyms
ValueSource
1-(4-{(1R)-1-[(6S,7S)-2-amino-7-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]ethylamino}phenyl)-1-deoxy-5-O-{5-O-[(1S)-1,3-dicarboxypropylphosphonato]-alpha-D-ribofuranosyl}-D-ribitolChEBI
H4MPTChEBI
TetrahydromethanopterinChEBI
THMPTKegg
1-(4-{(1R)-1-[(6S,7S)-2-amino-7-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]ethylamino}phenyl)-1-deoxy-5-O-{5-O-[(1S)-1,3-dicarboxypropylphosphonato]-a-D-ribofuranosyl}-D-ribitolGenerator
1-(4-{(1R)-1-[(6S,7S)-2-amino-7-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]ethylamino}phenyl)-1-deoxy-5-O-{5-O-[(1S)-1,3-dicarboxypropylphosphonato]-α-D-ribofuranosyl}-D-ribitolGenerator
Chemical FormulaC30H45N6O16P
Average Molecular Weight776.6827
Monoisotopic Molecular Weight776.262965934
IUPAC Name(2S)-2-[({[(2R,3S,4R,5S)-3,4-dihydroxy-5-{[(2R,3S,4S)-2,3,4-trihydroxy-5-(4-{[(1R)-1-[(6S,7S)-4-hydroxy-2-imino-7-methyl-1,2,5,6,7,8-hexahydropteridin-6-yl]ethyl]amino}phenyl)pentyl]oxy}oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]pentanedioic acid
Traditional Name(2S)-2-({[(2R,3S,4R,5S)-3,4-dihydroxy-5-{[(2R,3S,4S)-2,3,4-trihydroxy-5-(4-{[(1R)-1-[(6S,7S)-4-hydroxy-2-imino-7-methyl-5,6,7,8-tetrahydro-1H-pteridin-6-yl]ethyl]amino}phenyl)pentyl]oxy}oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)pentanedioic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](NC1=CC=C(C[C@H](O)[C@H](O)[C@H](O)CO[C@H]2O[C@H](COP(O)(=O)O[C@@H](CCC(O)=O)C(O)=O)[C@@H](O)[C@H]2O)C=C1)[C@@H]1NC2=C(N[C@H]1C)NC(=N)N=C2O
InChI Identifier
InChI=1S/C30H45N6O16P/c1-12(21-13(2)33-26-22(34-21)27(44)36-30(31)35-26)32-15-5-3-14(4-6-15)9-16(37)23(41)17(38)10-49-29-25(43)24(42)19(51-29)11-50-53(47,48)52-18(28(45)46)7-8-20(39)40/h3-6,12-13,16-19,21,23-25,29,32,34,37-38,41-43H,7-11H2,1-2H3,(H,39,40)(H,45,46)(H,47,48)(H4,31,33,35,36,44)/t12-,13+,16+,17-,18+,19-,21+,23+,24-,25-,29+/m1/s1
InChI KeySCBIBGUJSMHIAI-LHIIQLEZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Pterin
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide phosphate
  • Pteridine
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Pyrimidone
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Sugar acid
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Vinylogous amide
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Amine
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP-0.94ALOGPS
logP-5.8ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area354.53 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity198.53 m³·mol⁻¹ChemAxon
Polarizability73.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-1811011900-2412775d3b69d66421e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-5269630600-4b14907da135dddfda37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-9720010000-77bc0665e8cbb981dabfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1119400800-2b2e1d922403fefb3ac2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-3179101300-a0c3644acef6f4692310Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9230000000-08044b09315fd12dd4fcSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01217
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462234
PDB IDNot Available
ChEBI ID17321
Food Biomarker OntologyNot Available
VMH IDH4MPT
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Required to prevent uracil accumulation in mtDNA. Interconversion of serine and glycine. Associates with mitochondrial DNA.
Gene Name:
SHMT2
Uniprot ID:
P34897
Molecular weight:
54862.125
Reactions
L-Serine + 5,6,7,8-Tetrahydromethanopterin → 5,10-Methylenetetrahydromethanopterin + Glycine + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine.
Gene Name:
SHMT1
Uniprot ID:
P34896
Molecular weight:
53082.18
Reactions
L-Serine + 5,6,7,8-Tetrahydromethanopterin → 5,10-Methylenetetrahydromethanopterin + Glycine + Waterdetails