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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 15:13:09 UTC
Update Date2021-09-26 23:10:28 UTC
HMDB IDHMDB0255552
Secondary Accession NumbersNone
Metabolite Identification
Common NameNetupitant
DescriptionNetupitant belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Netupitant is a very strong basic compound (based on its pKa). A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2--2-methylpropanoic acid with the secondary amino group of N-methyl-4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-amine; an antiemetic used in combination with palonosetron hydrochloride (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy. This compound has been identified in human blood as reported by (PMID: 31557052 ). Netupitant is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Netupitant is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
ro-673189000NetupitantChEMBL
Chemical FormulaC30H32F6N4O
Average Molecular Weight578.603
Monoisotopic Molecular Weight578.248030644
IUPAC Name2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide
Traditional Namenetupitant
CAS Registry NumberNot Available
SMILES
CN(C(=O)C(C)(C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CN=C(C=C1C1=CC=CC=C1C)N1CCN(C)CC1
InChI Identifier
InChI=1S/C30H32F6N4O/c1-19-8-6-7-9-23(19)24-17-26(40-12-10-38(4)11-13-40)37-18-25(24)39(5)27(41)28(2,3)20-14-21(29(31,32)33)16-22(15-20)30(34,35)36/h6-9,14-18H,10-13H2,1-5H3
InChI KeyWAXQNWCZJDTGBU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Beta-hydroxy acid
  • Pyranone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.48ALOGPS
logP7.26ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)7.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity148.59 m³·mol⁻¹ChemAxon
Polarizability55.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+225.53630932474
DeepCCS[M-H]-223.64130932474
DeepCCS[M-2H]-256.88330932474
DeepCCS[M+Na]+231.31530932474
AllCCS[M+H]+231.732859911
AllCCS[M+H-H2O]+230.232859911
AllCCS[M+NH4]+233.132859911
AllCCS[M+Na]+233.432859911
AllCCS[M-H]-216.632859911
AllCCS[M+Na-2H]-217.132859911
AllCCS[M+HCOO]-217.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NetupitantCN(C(=O)C(C)(C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CN=C(C=C1C1=CC=CC=C1C)N1CCN(C)CC13145.2Standard polar33892256
NetupitantCN(C(=O)C(C)(C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CN=C(C=C1C1=CC=CC=C1C)N1CCN(C)CC13156.2Standard non polar33892256
NetupitantCN(C(=O)C(C)(C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CN=C(C=C1C1=CC=CC=C1C)N1CCN(C)CC13100.2Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Netupitant 10V, Positive-QTOFsplash10-004i-0020090000-4ef5b076f04ce35aefec2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Netupitant 20V, Positive-QTOFsplash10-014i-0090030000-2717ece211d627cd2e622017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Netupitant 40V, Positive-QTOFsplash10-0a4r-1090000000-f3d12f504e97b4dd0d792017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Netupitant 10V, Negative-QTOFsplash10-004i-0000090000-178518f2a8c25ebd7de42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Netupitant 20V, Negative-QTOFsplash10-004i-2023090000-1135ddd7970ff10e5d2d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Netupitant 40V, Negative-QTOFsplash10-0ckd-7391120000-d401b9c98f4339f69d332017-07-26Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09048
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNetupitant
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID85155
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]