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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 15:57:15 UTC
Update Date2019-01-11 19:19:25 UTC
HMDB IDHMDB0006559
Secondary Accession Numbers
  • HMDB06559
Metabolite Identification
Common NameHeptaglutamyl folic acid
DescriptionHeptaglutamyl folic acid is a naturally occurring form of folate. In contrast to synthetic folic acid, natural food folates are predominantly polyglutamates with a variable number of glutamate residues. (PMID 15831124 ). Approximately two-thirds of total folate intake from a mixed unfortified diet is in the polyglutamyl form, derived mainly from vegetables. These polyglutamates need to be hydrolysed to the monoglutamate form for normal absorption in the proximal small intestine. This process is controlled by the intestinal brush-border enzyme glutamate carboxypeptidase II (GCPII). (PMID 12042451 ).
Structure
Data?1547234365
SynonymsNot Available
Chemical FormulaC54H68N14O27
Average Molecular Weight1345.1953
Monoisotopic Molecular Weight1344.43783304
IUPAC Name(3S,9S)-3,9-diamino-5,6,6-tris[(2S)-2-amino-4-carboxybutanoyl]-7-{N-[(2S)-2-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(2S)-2-amino-4-carboxybutanoyl]oxy}carbonyl)-4,8-dioxoundecane-1,5,11-tricarboxylic acid
Traditional Name(3S,9S)-3,9-diamino-5,6,6-tris[(2S)-2-amino-4-carboxybutanoyl]-7-{N-[(2S)-2-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-3H-pteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(2S)-2-amino-4-carboxybutanoyl]oxy}carbonyl)-4,8-dioxoundecane-1,5,11-tricarboxylic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](CCC(O)=O)C(=O)OC(=O)C(N(C(=O)[C@@H](N)CCC(O)=O)C(=O)C1=CC=C(NCC2=NC3=C(N=C2)N=C(N)NC3=O)C=C1)(C(=O)[C@@H](N)CCC(O)=O)C(C(=O)[C@@H](N)CCC(O)=O)(C(=O)[C@@H](N)CCC(O)=O)C(C(O)=O)(C(=O)[C@@H](N)CCC(O)=O)C(=O)[C@@H](N)CCC(O)=O
InChI Identifier
InChI=1S/C54H68N14O27/c55-24(5-12-31(69)70)39(83)52(49(92)93,40(84)25(56)6-13-32(71)72)53(41(85)26(57)7-14-33(73)74,42(86)27(58)8-15-34(75)76)54(43(87)28(59)9-16-35(77)78,50(94)95-48(91)30(61)11-18-37(81)82)68(47(90)29(60)10-17-36(79)80)46(89)21-1-3-22(4-2-21)63-19-23-20-64-44-38(65-23)45(88)67-51(62)66-44/h1-4,20,24-30,63H,5-19,55-61H2,(H,69,70)(H,71,72)(H,73,74)(H,75,76)(H,77,78)(H,79,80)(H,81,82)(H,92,93)(H3,62,64,66,67,88)/t24-,25-,26-,27-,28-,29-,30-,54?/m0/s1
InChI KeyKNLHIYYNBQALAI-IMYKNWLQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Alpha-amino acid amide
  • Pterin
  • Gamma amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Pteridine
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Aniline or substituted anilines
  • Gamma-keto acid
  • Phenylalkylamine
  • Benzoyl
  • Beta-keto acid
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Amino fatty acid
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Fatty acyl
  • Beta-hydroxy ketone
  • Gamma-aminoketone
  • Benzenoid
  • Keto acid
  • N-acyl-amine
  • Carboxylic acid imide, n-substituted
  • Pyrimidine
  • Pyrazine
  • Vinylogous amide
  • Heteroaromatic compound
  • Dicarboximide
  • Alpha-aminoketone
  • Carboxylic acid imide
  • Carboxylic acid anhydride
  • Amino acid
  • Amino acid or derivatives
  • Ketone
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP-2.9ALOGPS
logP-5.9ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count38ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area751.93 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity309.73 m³·mol⁻¹ChemAxon
Polarizability126.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0219000000-de96feac7a5f037e6ed7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ba-0965000000-ca787bcf51d16c5d692aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bj-2951000000-0143d67eac83321cfdc8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-0973000000-6a9d143b843aaeb9b401JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-005a-1491000000-aa3e5825dbab41cff58eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-2930000020-43433206d0ffd698903cJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0076 (0.0038-0.0115) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023971
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2304198
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477856
PDB IDNot Available
ChEBI ID89846
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. McNulty H, Pentieva K: Folate bioavailability. Proc Nutr Soc. 2004 Nov;63(4):529-36. [PubMed:15831124 ]
  2. Melse-Boonstra A, de Bree A, Verhoef P, Bjorke-Monsen AL, Verschuren WM: Dietary monoglutamate and polyglutamate folate are associated with plasma folate concentrations in Dutch men and women aged 20-65 years. J Nutr. 2002 Jun;132(6):1307-12. [PubMed:12042451 ]