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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015539
Secondary Accession Numbers
  • HMDB15539
Metabolite Identification
Common NameLopinavir
DescriptionLopinavir is only found in individuals that have used or taken this drug. It is an antiretroviral of the protease inhibitor class. It is marketed by Abbott as Kaletra, a co-formulation with a sub-therapeutic dose of ritonavir, as a component of combination therapy to treat HIV/AIDS.Lopinavir inhibits the HIV viral protease enzyme. This prevents cleavage of the gag-pol polyprotein and, therefore, improper viral assembly results. This subsequently results in non-infectious, immature viral particles.
Structure
Data?1582753307
Synonyms
ValueSource
KaletraHMDB
ABT-378a-157378-0a-157378.0HMDB
ABT-378HMDB
LPVHMDB
378, ABTHMDB
N-(4-(((2,6-Dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pydrimidineacetamideHMDB
ABT 378HMDB
Chemical FormulaC37H48N4O5
Average Molecular Weight628.8008
Monoisotopic Molecular Weight628.362470666
IUPAC Name(2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
Traditional Namelopinavir
CAS Registry Number192725-17-0
SMILES
CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)COC1=C(C)C=CC=C1C)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1
InChI KeyKJHKTHWMRKYKJE-SUGCFTRWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentValine and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • Amphetamine or derivatives
  • Phenoxy compound
  • Phenol ether
  • M-xylene
  • Xylene
  • Alkyl aryl ether
  • Pyrimidone
  • Monocyclic benzene moiety
  • 1,3-diazinane
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Pyrimidine
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Urea
  • Carboxamide group
  • Carbonic acid derivative
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0019 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP3.91ALOGPS
logP4.69ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)13.39ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity179.36 m³·mol⁻¹ChemAxon
Polarizability69.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+242.90231661259
DarkChem[M-H]-230.39131661259
DeepCCS[M+H]+248.34130932474
DeepCCS[M-H]-246.51630932474
DeepCCS[M-2H]-279.75730932474
DeepCCS[M+Na]+253.94730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LopinavirCC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)COC1=C(C)C=CC=C1C)CC1=CC=CC=C15382.0Standard polar33892256
LopinavirCC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)COC1=C(C)C=CC=C1C)CC1=CC=CC=C13972.8Standard non polar33892256
LopinavirCC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)COC1=C(C)C=CC=C1C)CC1=CC=CC=C14999.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lopinavir,1TMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C4774.8Semi standard non polar33892256
Lopinavir,1TMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O4623.5Semi standard non polar33892256
Lopinavir,1TMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C4710.0Semi standard non polar33892256
Lopinavir,1TMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C4676.4Semi standard non polar33892256
Lopinavir,2TMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C)[Si](C)(C)C4683.1Semi standard non polar33892256
Lopinavir,2TMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C)[Si](C)(C)C4065.9Standard non polar33892256
Lopinavir,2TMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C)[Si](C)(C)C6275.9Standard polar33892256
Lopinavir,2TMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)O[Si](C)(C)C4667.1Semi standard non polar33892256
Lopinavir,2TMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)O[Si](C)(C)C3988.2Standard non polar33892256
Lopinavir,2TMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)O[Si](C)(C)C6250.0Standard polar33892256
Lopinavir,2TMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)O[Si](C)(C)C4613.1Semi standard non polar33892256
Lopinavir,2TMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)O[Si](C)(C)C4076.3Standard non polar33892256
Lopinavir,2TMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)O[Si](C)(C)C6158.3Standard polar33892256
Lopinavir,2TMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C4493.7Semi standard non polar33892256
Lopinavir,2TMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C4148.8Standard non polar33892256
Lopinavir,2TMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C6259.2Standard polar33892256
Lopinavir,2TMS,isomer #5CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C4547.7Semi standard non polar33892256
Lopinavir,2TMS,isomer #5CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C4120.5Standard non polar33892256
Lopinavir,2TMS,isomer #5CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C6262.8Standard polar33892256
Lopinavir,2TMS,isomer #6CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)[Si](C)(C)C4606.3Semi standard non polar33892256
Lopinavir,2TMS,isomer #6CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)[Si](C)(C)C4043.9Standard non polar33892256
Lopinavir,2TMS,isomer #6CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)[Si](C)(C)C6350.3Standard polar33892256
Lopinavir,3TMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C4628.6Semi standard non polar33892256
Lopinavir,3TMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C4015.6Standard non polar33892256
Lopinavir,3TMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C5965.6Standard polar33892256
Lopinavir,3TMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)O[Si](C)(C)C)[Si](C)(C)C4550.7Semi standard non polar33892256
Lopinavir,3TMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)O[Si](C)(C)C)[Si](C)(C)C4094.0Standard non polar33892256
Lopinavir,3TMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)O[Si](C)(C)C)[Si](C)(C)C5907.0Standard polar33892256
Lopinavir,3TMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C)O[Si](C)(C)C4556.6Semi standard non polar33892256
Lopinavir,3TMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C)O[Si](C)(C)C4075.7Standard non polar33892256
Lopinavir,3TMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C)O[Si](C)(C)C5897.5Standard polar33892256
Lopinavir,3TMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C)[Si](C)(C)C4478.1Semi standard non polar33892256
Lopinavir,3TMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C)[Si](C)(C)C4150.3Standard non polar33892256
Lopinavir,3TMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C)C1=O)[Si](C)(C)C)[Si](C)(C)C6004.1Standard polar33892256
Lopinavir,1TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C(C)(C)C4986.8Semi standard non polar33892256
Lopinavir,1TBDMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O4871.0Semi standard non polar33892256
Lopinavir,1TBDMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C4898.2Semi standard non polar33892256
Lopinavir,1TBDMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C4859.1Semi standard non polar33892256
Lopinavir,2TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C5050.7Semi standard non polar33892256
Lopinavir,2TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4373.1Standard non polar33892256
Lopinavir,2TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCNC1=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C6208.9Standard polar33892256
Lopinavir,2TBDMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C5053.8Semi standard non polar33892256
Lopinavir,2TBDMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4313.2Standard non polar33892256
Lopinavir,2TBDMS,isomer #2CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C6182.2Standard polar33892256
Lopinavir,2TBDMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)O[Si](C)(C)C(C)(C)C5040.8Semi standard non polar33892256
Lopinavir,2TBDMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)O[Si](C)(C)C(C)(C)C4315.1Standard non polar33892256
Lopinavir,2TBDMS,isomer #3CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)O[Si](C)(C)C(C)(C)C6119.1Standard polar33892256
Lopinavir,2TBDMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C4913.4Semi standard non polar33892256
Lopinavir,2TBDMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C4359.1Standard non polar33892256
Lopinavir,2TBDMS,isomer #4CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C6201.4Standard polar33892256
Lopinavir,2TBDMS,isomer #5CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C4971.0Semi standard non polar33892256
Lopinavir,2TBDMS,isomer #5CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C4357.8Standard non polar33892256
Lopinavir,2TBDMS,isomer #5CC1=CC=CC(C)=C1OCC(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCN([Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C6207.3Standard polar33892256
Lopinavir,2TBDMS,isomer #6CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4994.1Semi standard non polar33892256
Lopinavir,2TBDMS,isomer #6CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4351.2Standard non polar33892256
Lopinavir,2TBDMS,isomer #6CC1=CC=CC(C)=C1OCC(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)C[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](C(C)C)N1CCCNC1=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C6260.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (Non-derivatized) - 70eV, Positivesplash10-0feu-6925370000-713b224b442e85bb346b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lopinavir GC-MS ("Lopinavir,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Lopinavir , positive-QTOFsplash10-0fb9-0119005000-e99616dc321beea979ae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lopinavir , positive-QTOFsplash10-0532-1900601000-f85a252f1640f27563a82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lopinavir 50V, Positive-QTOFsplash10-0a4i-0900000000-3578e2c32c774a6e323f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lopinavir 10V, Positive-QTOFsplash10-004j-0000309000-34a01a3fe1b7908567ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lopinavir 20V, Positive-QTOFsplash10-000t-0500900000-b26acb5f91e9e55a6be52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lopinavir 40V, Positive-QTOFsplash10-0a4i-0900000000-b4ad3519debd6ec500662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lopinavir 30V, Positive-QTOFsplash10-053r-0900400000-81442626229760ffe4132021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 10V, Positive-QTOFsplash10-03fs-0210908000-054ffc2d70c7a928ed3e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 20V, Positive-QTOFsplash10-0bwa-0711911000-c9c5439ab7698ec8fd812016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 40V, Positive-QTOFsplash10-05ai-3940000000-e1de250134ecffc3ae812016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 10V, Negative-QTOFsplash10-004i-1600309000-a5fe821e3d663cb119612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 20V, Negative-QTOFsplash10-00dl-4900101000-49d4f32903902eae73e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 40V, Negative-QTOFsplash10-0006-9400000000-2399e0947eb63c53c2442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 10V, Positive-QTOFsplash10-056r-0300659000-e86c051846f2ce85f44a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 20V, Positive-QTOFsplash10-0550-2900532000-9df9f0a93610394f84a12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 40V, Positive-QTOFsplash10-052k-4900100000-fa68120128333a7571352021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 10V, Negative-QTOFsplash10-004i-0712669000-93271ad3fea09b7fa4582021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 20V, Negative-QTOFsplash10-0a4r-5603950000-6e950fa2e516bd0177a42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lopinavir 40V, Negative-QTOFsplash10-01b9-5901100000-03be5213ed13f46963882021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01601 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01601 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01601
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID83706
KEGG Compound IDC12871
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLopinavir
METLIN IDNot Available
PubChem Compound92727
PDB IDAB1
ChEBI ID31781
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 ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Vishnuvardhan D, Moltke LL, Richert C, Greenblatt DJ: Lopinavir: acute exposure inhibits P-glycoprotein; extended exposure induces P-glycoprotein. AIDS. 2003 May 2;17(7):1092-4. [PubMed:12700464 ]