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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:20:34 UTC
Update Date2021-09-26 23:07:58 UTC
HMDB IDHMDB0254156
Secondary Accession NumbersNone
Metabolite Identification
Common NameLomitapide
DescriptionLomitapide, also known as aegr 733 or BMS 201038, belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. Lomitapide is a drug which is used in homozygous familial hypercholesterolemia (hofh) patients to reduce low-density lipoprotein cholesterol (ldl-c), total cholesterol (tc), apolipoprotein b (apo b), and non-high-density lipoprotein cholesterol (non-hdl-c). Based on a literature review a significant number of articles have been published on Lomitapide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lomitapide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lomitapide 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
AEGR 733ChEBI
AEGR 773ChEBI
AEGR-733ChEBI
AEGR-773ChEBI
AEGR733ChEBI
AEGR773ChEBI
BMS 201038ChEBI
BMS-201038ChEBI
BMS201038ChEBI
JuxtapidChEBI
LojuxtaChEBI
LomitapidaChEBI
LomitapidumChEBI
Chemical FormulaC39H37F6N3O2
Average Molecular Weight693.7204
Monoisotopic Molecular Weight693.278996673
IUPAC NameN-(2,2,2-trifluoroethyl)-9-[4-(4-{2-[4-(trifluoromethyl)phenyl]benzamido}piperidin-1-yl)butyl]-9H-fluorene-9-carboxamide
Traditional Namelomitapide
CAS Registry NumberNot Available
SMILES
FC(F)(F)CNC(=O)C1(CCCCN2CCC(CC2)NC(=O)C2=C(C=CC=C2)C2=CC=C(C=C2)C(F)(F)F)C2=CC=CC=C2C2=CC=CC=C12
InChI Identifier
InChI=1S/C39H37F6N3O2/c40-38(41,42)25-46-36(50)37(33-13-5-3-10-30(33)31-11-4-6-14-34(31)37)21-7-8-22-48-23-19-28(20-24-48)47-35(49)32-12-2-1-9-29(32)26-15-17-27(18-16-26)39(43,44)45/h1-6,9-18,28H,7-8,19-25H2,(H,46,50)(H,47,49)
InChI KeyMBBCVAKAJPKAKM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassFluorenes
Sub ClassNot Available
Direct ParentFluorenes
Alternative Parents
Substituents
  • Fluorene
  • Biphenyl
  • Trifluoromethylbenzene
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • Piperidine
  • Fatty acyl
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Amine
  • Alkyl halide
  • Hydrocarbon derivative
  • Organohalogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organofluoride
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP7.7ChemAxon
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)9.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.44 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity181.73 m³·mol⁻¹ChemAxon
Polarizability68.08 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-277.74430932474
DeepCCS[M+Na]+252.1530932474
AllCCS[M+H]+251.332859911
AllCCS[M+H-H2O]+250.832859911
AllCCS[M+NH4]+251.632859911
AllCCS[M+Na]+251.732859911
AllCCS[M-H]-231.632859911
AllCCS[M+Na-2H]-234.032859911
AllCCS[M+HCOO]-236.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LomitapideFC(F)(F)CNC(=O)C1(CCCCN2CCC(CC2)NC(=O)C2=C(C=CC=C2)C2=CC=C(C=C2)C(F)(F)F)C2=CC=CC=C2C2=CC=CC=C124599.5Standard polar33892256
LomitapideFC(F)(F)CNC(=O)C1(CCCCN2CCC(CC2)NC(=O)C2=C(C=CC=C2)C2=CC=C(C=C2)C(F)(F)F)C2=CC=CC=C2C2=CC=CC=C124414.0Standard non polar33892256
LomitapideFC(F)(F)CNC(=O)C1(CCCCN2CCC(CC2)NC(=O)C2=C(C=CC=C2)C2=CC=C(C=C2)C(F)(F)F)C2=CC=CC=C2C2=CC=CC=C124316.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lomitapide,1TMS,isomer #1C[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(NC(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)CC2)C2=CC=CC=C2C2=CC=CC=C214386.1Semi standard non polar33892256
Lomitapide,1TMS,isomer #1C[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(NC(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)CC2)C2=CC=CC=C2C2=CC=CC=C214402.1Standard non polar33892256
Lomitapide,1TMS,isomer #1C[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(NC(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)CC2)C2=CC=CC=C2C2=CC=CC=C214885.9Standard polar33892256
Lomitapide,1TMS,isomer #2C[Si](C)(C)N(C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1)C1CCN(CCCCC2(C(=O)NCC(F)(F)F)C3=CC=CC=C3C3=CC=CC=C32)CC14290.3Semi standard non polar33892256
Lomitapide,1TMS,isomer #2C[Si](C)(C)N(C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1)C1CCN(CCCCC2(C(=O)NCC(F)(F)F)C3=CC=CC=C3C3=CC=CC=C32)CC14400.3Standard non polar33892256
Lomitapide,1TMS,isomer #2C[Si](C)(C)N(C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1)C1CCN(CCCCC2(C(=O)NCC(F)(F)F)C3=CC=CC=C3C3=CC=CC=C32)CC14899.8Standard polar33892256
Lomitapide,2TMS,isomer #1C[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(N(C(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)[Si](C)(C)C)CC2)C2=CC=CC=C2C2=CC=CC=C214336.3Semi standard non polar33892256
Lomitapide,2TMS,isomer #1C[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(N(C(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)[Si](C)(C)C)CC2)C2=CC=CC=C2C2=CC=CC=C214477.2Standard non polar33892256
Lomitapide,2TMS,isomer #1C[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(N(C(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)[Si](C)(C)C)CC2)C2=CC=CC=C2C2=CC=CC=C214723.0Standard polar33892256
Lomitapide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(NC(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)CC2)C2=CC=CC=C2C2=CC=CC=C214551.6Semi standard non polar33892256
Lomitapide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(NC(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)CC2)C2=CC=CC=C2C2=CC=CC=C214590.6Standard non polar33892256
Lomitapide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC(F)(F)F)C(=O)C1(CCCCN2CCC(NC(=O)C3=CC=CC=C3C3=CC=C(C(F)(F)F)C=C3)CC2)C2=CC=CC=C2C2=CC=CC=C214918.6Standard polar33892256
Lomitapide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1)C1CCN(CCCCC2(C(=O)NCC(F)(F)F)C3=CC=CC=C3C3=CC=CC=C32)CC14451.5Semi standard non polar33892256
Lomitapide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1)C1CCN(CCCCC2(C(=O)NCC(F)(F)F)C3=CC=CC=C3C3=CC=CC=C32)CC14590.9Standard non polar33892256
Lomitapide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1)C1CCN(CCCCC2(C(=O)NCC(F)(F)F)C3=CC=CC=C3C3=CC=CC=C32)CC14912.7Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 10V, Positive-QTOFsplash10-0006-2001219000-6355e4523ebce81ed3932017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 20V, Positive-QTOFsplash10-0002-6094133000-d842bc906f7937f345a62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 40V, Positive-QTOFsplash10-0002-6197010000-2b0fad84ddf4e6015aab2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 10V, Negative-QTOFsplash10-0006-0000009000-01f058276a30a0a90ae62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 20V, Negative-QTOFsplash10-00dl-2151129000-9f4ee77b1cebb71541182017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 40V, Negative-QTOFsplash10-022d-6292000000-6929238400efb8154d632017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 10V, Positive-QTOFsplash10-0007-0060009000-10cb69936336e337e2682021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 20V, Positive-QTOFsplash10-0006-0010019000-6c05809839268e373f802021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 40V, Positive-QTOFsplash10-05mk-1591502000-cb9f29bb9ef3e2d474ab2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 10V, Negative-QTOFsplash10-0006-0000009000-55d8427fb7c8c430fede2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 20V, Negative-QTOFsplash10-0006-8234439000-2a478d85425a9ab20f2c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lomitapide 40V, Negative-QTOFsplash10-0fmm-3589022000-15e1237fab50004167d42021-10-12Wishart 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 IDDB08827
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8028764
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLomitapide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID72297
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 ]