ContaminantDB: Lopinavir

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:45:13 UTC

Update Date

2016-11-09 01:15:54 UTC

Accession Number

CHEM019005

Identification

Common Name

Lopinavir

Class

Small Molecule

Description

Lopinavir is an antiretroviral protease inhibitor used in combination with other antiretrovirals in the treatment of HIV-1 infection. Lopinavir is marketed and administered exclusively in combination with - this combination, first marketed by Abbott under the brand name Lopinavir in 2000, is necessary due to lopinavir's poor oral bioavailability and extensive biotransformation. Ritonavir is a potent inhibitor of the enzymes responsible for lopinavir metabolism, and its co-administration "boosts" lopinavir exposure and improves antiviral activity. Like many other protease inhibitors (e.g. , ), lopinavir is a peptidomimetic molecule - it contains a hydroxyethylene scaffold that mimics the peptide linkage typically targeted by the HIV-1 protease enzyme but which itself cannot be cleaved, thus preventing the activity of the HIV-1 protease. Lopinavir is currently under investigation in combination with ritonavir for the treatment of COVID-19 caused by SARS-CoV-2.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Kaletra	HMDB
ABT-378a-157378-0a-157378.0	HMDB
ABT-378	HMDB
LPV	HMDB
378, ABT	HMDB
N-(4-(((2,6-Dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pydrimidineacetamide	HMDB
ABT 378	HMDB

Chemical Formula

C₃₇H₄₈N₄O₅

Average Molecular Mass

628.801 g/mol

Monoisotopic Mass

628.362 g/mol

CAS Registry Number

192725-17-0

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 Name

lopinavir

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 Key

KJHKTHWMRKYKJE-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Valine 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid diamide (CHEBI:31781 )
amphetamines (CHEBI:31781 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0019 g/L	ALOGPS
logP	3.91	ALOGPS
logP	4.69	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	179.36 m³·mol⁻¹	ChemAxon
Polarizability	69.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0feu-6925370000-713b224b442e85bb346b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Lopinavir,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0fb9-0119005000-e99616dc321beea979ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0532-1900601000-f85a252f1640f27563a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-0900000000-3578e2c32c774a6e323f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0000309000-34a01a3fe1b7908567ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0500900000-b26acb5f91e9e55a6be5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-b4ad3519debd6ec50066	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-0900400000-81442626229760ffe413	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fs-0210908000-054ffc2d70c7a928ed3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bwa-0711911000-c9c5439ab7698ec8fd81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05ai-3940000000-e1de250134ecffc3ae81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1600309000-a5fe821e3d663cb11961	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-4900101000-49d4f32903902eae73e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-2399e0947eb63c53c244	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0300659000-e86c051846f2ce85f44a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0550-2900532000-9df9f0a93610394f84a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052k-4900100000-fa68120128333a757135	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0712669000-93271ad3fea09b7fa458	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-5603950000-6e950fa2e516bd0177a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01b9-5901100000-03be5213ed13f4696388	Spectrum