Darunavir (CED0003103)

Record Information

Version

1.0

Creation Date

2016-05-22 05:56:42 UTC

Update Date

2026-08-22 07:42:45 UTC

Accession Number

CHEM019245

Identification

Common Name

Darunavir

Class

Small Molecule

Description

Darunavir is an organic compound with the chemical formula C27H37N3O7S. Darunavir belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 547.66 g/mol, Darunavir is a heavy molecule. This compound has been identified in or released from five recorded sources. These include pharmaceuticals and veterinary products, specifically antivirals and gynecologicals, as well as electrical and electronic equipment such as video games and television systems. Additionally, it is found in household cleaning and consumer products, specifically non electric simulated smoking devices. The recorded route of exposure for this substance is oral. In terms of biological activity, Darunavir interacts with two recorded protein targets. It functions as an inhibitor or modulator of the Pol polyprotein and the Gag-Pol polyprotein (gag-pol).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamate	ChEBI
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamATE	ChEBI
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	ChEBI
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	ChEBI
[(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	ChEBI
Darunavirum	ChEBI
N-((1S,2R)-3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamide	ChEBI
TMC114	ChEBI
{(1S,2R)-3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	ChEBI
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamic acid	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulphanilamido)propyl)carbamate	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulphanilamido)propyl)carbamic acid	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamic acid	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulphonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulphonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
[(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
[(S)-3-[(4-Amino-benzenesulphonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
[(S)-3-[(4-Amino-benzenesulphonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
N-((1S,2R)-3-(((4-Aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamide	Generator
{(1S,2R)-3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
{(1S,2R)-3-[(4-amino-benzenesulphonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
{(1S,2R)-3-[(4-amino-benzenesulphonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
AIDS073035	HMDB
TMC-114	HMDB
UIC-94017	HMDB
114, TMC	HMDB
TMC 114	HMDB
Ethanolate, darunavir	HMDB
Darunavir ethanolate	HMDB
Prezista	HMDB

Chemical Formula

C₂₇H₃₇N₃O₇S

Average Molecular Mass

547.664 g/mol

Monoisotopic Mass

547.235 g/mol

CAS Registry Number

206361-99-1

IUPAC Name

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

Traditional Name

darunavir

SMILES

[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1

InChI Key

CJBJHOAVZSMMDJ-HEXNFIEUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Phenylbutylamine
Amphetamine or derivatives
Benzenesulfonyl group
Furofuran
Aniline or substituted anilines
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Tetrahydrofuran
Carbamic acid ester
Aminosulfonyl compound
Secondary alcohol
Carbonic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary amine
Organopnictogen compound
Carbonyl group
Amine
Organic nitrogen compound
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:367163 )
sulfonamide (CHEBI:367163 )
furofuran (CHEBI:367163 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	0.067 g/L	ALOGPS
logP	1.76	ALOGPS
logP	2.82	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.42 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	142.34 m³·mol⁻¹	ChemAxon
Polarizability	57.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-7395120000-9ee6643d8e957bfc6883	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-08i3-8659131000-a5895dfe8fa0c5374f22	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0aor-0900800000-e427a102e3a7551cc732	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0900000000-8ab8c2b3421f4a277282	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2900000000-eddacc917eaf16abe9d2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2900000000-86c785caeafe3b4a10c3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4l-5900000000-69bc90a59383cb5a804b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4l-8900000000-f481d0932a99692c87d9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000g-0009760000-f730e27547a482694ebc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0009000000-fcd18a6f4e9084f0f8f1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0469000000-716a2ae87ad9df6765fb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0941000000-5e0dbe51025009642b33	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0910000000-2411514d55bfa3c4e81f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-2309000000-e6767f5d8648334c41c9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9621000000-3a7c794f5e3f473b9ad5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9400000000-16b363cdd836532460ce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2900000000-98bfa9c688e4cb2dbbc3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4l-4900000000-05c5a10ff111a5d1c9bf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052f-6900000000-f59c1c0d97f0a8ab00d7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0900000000-40373637b670c5395ffd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0aor-0900800000-f59913cdbcd62042530a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2900000000-10dadadeebe1e6ec0164	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0009000000-8e1cc4b8ca6f49bcfe56	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000g-0009760000-26cdc56a39511d44e965	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-2309000000-b56fe3acae7c21ddaba0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0941000000-5e0dbe51025009642b33	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0469000000-c470e3e505d43b7089af	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0941000000-1bfc191c3ef7c76e399a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0469000000-716a2ae87ad9df6765fb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0469000000-88a2aa3a18e68a6a8c87	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0009000000-cd24e55f9cffee600214	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0910000000-2411514d55bfa3c4e81f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000g-0009760000-3737a6b429e0f4409291	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000g-0009760000-f730e27547a482694ebc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0931000000-eca02149631677bcfffb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0920000000-6021e5dbfe305dd0d6e8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9400000000-f273ebedf1f30673e27a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0931000000-a21e0c76b0d45400f9a4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-9621000000-d2b39c8b2f2aa174b4f1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a59-9401140000-56eac45c2f7be4c47482	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9301000000-bb8cecd1683edef150fe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9100000000-08319e638dc9213da395	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00mk-0805970000-4bf40ac64acd286d67f2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-2933410000-f89d6de3a367503d41e5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05dl-4933200000-1375ea05a3f120000d76	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ot-1824290000-f54a2a5d6339d60e43df	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08fu-2910210000-e350bf727a2edf01f5d6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-9100000000-31fd1c1da3df0c11b9f6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900240000-072c834a66c41bb38b74	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2902210000-7da1d822e71f91c229c9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-054o-2901000000-d4858cb299ffb926598e	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
649.0	Log mg/kg	[360:1200]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
316	Gynecologicals	Healthcare, pharmaceuticals & veterinary products	Not Available
351	Antivirals	Healthcare, pharmaceuticals & veterinary products	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Darunavir Action Pathway

Darunavir Drug Metabolism Action Pathway

Darunavir Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Protease	Q9YQ12	Human immunodeficiency virus 1	Predicted (SEA)	0.0778492
Click to view 3D structure	Pol polyprotein	Q72874	Human immunodeficiency virus 1	Predicted (SEA)	0.311397
Click to view 3D structure	Gag-Pol polyprotein	P03369	HIV-1	Predicted (SEA)	1.32344
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	18.6838
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	477.216
Click to view 3D structure	Thromboxane-A synthase	P24557	Humans	Predicted (SEA)	13.8572
Click to view 3D structure	Gamma-secretase subunit PEN-2	Q9NZ42	Humans	Predicted (SEA)	47.7994
Click to view 3D structure	Cytochrome P450 3A5	P20815	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Stromelysin-1	P08254	Humans	Predicted (SEA)	248.806
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	416.649
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	379.281
Click to view 3D structure	Interstitial collagenase	P03956	Humans	Predicted (SEA)	295.126
Click to view 3D structure	Renin	P00797	Humans	Predicted (SEA)	153.908
Click to view 3D structure	Neutrophil collagenase	P22894	Humans	Predicted (SEA)	306.959
Click to view 3D structure	Collagenase 3	P45452	Humans	Predicted (SEA)	345.962
Click to view 3D structure	Cathepsin D	P07339	Humans	Predicted (SEA)	178.353
Click to view 3D structure	Human rhinovirus A protease	Q4U254	Human rhinovirus sp.	Predicted (SEA)	64.8484
Click to view 3D structure	Beta-secretase 1	P56817	Humans	Predicted (SEA)	208.169
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	221.403
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	665.066
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	554.364
Click to view 3D structure	UDP-glucuronosyltransferase 1A1	Q64550	Rattus norvegicus	Predicted (SEA)	22.5763
Click to view 3D structure	Matrix metalloproteinase-14	P50281	Humans	Predicted (SEA)	401.235
Click to view 3D structure	Disintegrin and metalloproteinase domain-containing protein 17	P78536	Humans	Predicted (SEA)	273.406
Click to view 3D structure	Cholinesterase	P81908	Equus caballus	Predicted (SEA)	438.447