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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:44:43 UTC
HMDB IDHMDB0015649
Secondary Accession Numbers
  • HMDB15649
Metabolite Identification
Common NameGadobutrol
DescriptionGadobutrol, also known as gadavist or GD-do3a-butriol, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Gadobutrol is a drug which is used for diagnostic use only. indicated for adults and children age 2 and over for contrast enhancement during cranial and spinal mri, and for contrast-enhanced magnetic resonance angiography (ce-mra). gadobutrol is particularly suited for the detection of very small lesions and for the visualization of tumors that do not readily take up contrast media. it may be a desired agent when the exclusion or demonstration of an additional pathology may influence the choice of therapy or patient management. it may also be suitable for perfusion studies in the diagnosis of stroke, detection of focal cerebral ischemia, and in studies of tumor perfusion. . Based on a literature review a significant number of articles have been published on Gadobutrol.
Structure
Data?1582753320
Synonyms
ValueSource
GadavistChEBI
GadobutrolumChEBI
Gadolinium-do3a-butriolChEBI
GD-DO3a-butriolChEBI
Chemical FormulaC18H31GdN4O9
Average Molecular Weight604.72
Monoisotopic Molecular Weight605.13321
IUPAC Name4,7,10-tris(carboxymethyl)-1-[(2S,3R)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetraaza-13-gadolinatetracyclo[5.5.1.0^{4,13}.0^{10,13}]tridecane-1,4,7,10-tetraium-13-uide
Traditional Name4,7,10-tris(carboxymethyl)-1-[(2S,3R)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetraaza-13-gadolinatetracyclo[5.5.1.0^{4,13}.0^{10,13}]tridecane-1,4,7,10-tetraium-13-uide
CAS Registry Number138071-82-6
SMILES
OC[C@H](O)[C@H](CO)[N+]12CC[N+]3(CC([O-])=O)CC[N+]4(CC([O-])=O)CC[N+](CC([O-])=O)(CC1)[Gd-]234
InChI Identifier
InChI=1S/C18H34N4O9.Gd/c23-12-14(15(25)13-24)22-7-5-20(10-17(28)29)3-1-19(9-16(26)27)2-4-21(6-8-22)11-18(30)31;/h14-15,23-25H,1-13H2,(H,26,27)(H,28,29)(H,30,31);/q;+3/p-3/t14-,15-;/m0./s1
InChI KeyZPDFIIGFYAHNSK-YYLIZZNMSA-K
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • 1,3-aminoalcohol
  • 1,2-aminoalcohol
  • Carboxylic acid salt
  • Amino acid
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid
  • Polyol
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Alcohol
  • Organic salt
  • Organic zwitterion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility35.2 g/LALOGPS
logP10(0.35) g/LALOGPS
logP10(-4.6) g/LChemAxon
logS10(-4.2) g/LALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area181.08 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity143.47 m³·mol⁻¹ChemAxon
Polarizability45.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gadobutrol,1TMS,#1C[Si](C)(C)OC[C@H](O)[C@H](CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323775.9Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,1TMS,#2C[Si](C)(C)O[C@@H](CO)[C@H](CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323778.0Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,1TMS,#3C[Si](C)(C)OC[C@@H]([C@@H](O)CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323787.0Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,2TMS,#1C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H](CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323818.8Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,2TMS,#2C[Si](C)(C)OC[C@@H]([C@@H](O)CO[Si](C)(C)C)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323821.8Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,2TMS,#3C[Si](C)(C)OC[C@@H]([C@H](CO)O[Si](C)(C)C)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323825.4Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,3TMS,#1C[Si](C)(C)OC[C@@H]([C@H](CO[Si](C)(C)C)O[Si](C)(C)C)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323857.9Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,1TBDMS,#1CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H](CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323962.3Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,1TBDMS,#2CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@H](CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323973.0Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,1TBDMS,#3CC(C)(C)[Si](C)(C)OC[C@@H]([C@@H](O)CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4323982.5Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,2TBDMS,#1CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4324251.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,2TBDMS,#2CC(C)(C)[Si](C)(C)OC[C@@H]([C@@H](O)CO[Si](C)(C)C(C)(C)C)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4324251.6Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Gadobutrol,2TBDMS,#3CC(C)(C)[Si](C)(C)OC[C@@H]([C@H](CO)O[Si](C)(C)C(C)(C)C)[N+]12CC[N+]3(CC(=O)[O-])CC[N+]4(CC(=O)[O-])CC[N+](CC(=O)[O-])(CC1)[Gd-]4324244.4Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06703 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06703 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06703
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28533281
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGadobutrol
METLIN IDNot Available
PubChem Compound12041444
PDB IDNot Available
ChEBI ID68841
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kunnemeyer J, Terborg L, Nowak S, Scheffer A, Telgmann L, Tokmak F, Gunsel A, Wiesmuller G, Reichelt S, Karst U: Speciation analysis of gadolinium-based MRI contrast agents in blood plasma by hydrophilic interaction chromatography/electrospray mass spectrometry. Anal Chem. 2008 Nov 1;80(21):8163-70. doi: 10.1021/ac801264j. Epub 2008 Sep 27. [PubMed:18821778 ]
  2. Wack C, Steger-Hartmann T, Mylecraine L, Hofmeister R: Toxicological safety evaluation of gadobutrol. Invest Radiol. 2012 Nov;47(11):611-23. doi: 10.1097/RLI.0b013e318263f128. [PubMed:23011188 ]
  3. Scott LJ: Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children. Clin Drug Investig. 2013 Apr;33(4):303-14. doi: 10.1007/s40261-013-0066-0. [PubMed:23435930 ]