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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:efavirenz
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Accession:CHEBI:119486 term browser browse the term
Definition:1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.
Synonyms:related_synonym: (-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE;   (4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one;   (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one;   (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one;   6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one;   Formula=C14H9ClF3NO2;   InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1;   InChIKey=XPOQHMRABVBWPR-ZDUSSCGKSA-N;   SMILES=FC(F)(F)[C@]1(OC(=O)Nc2ccc(Cl)cc12)C#CC1CC1
 alt_id: CHEBI:190461;   CHEBI:47396;   CHEBI:4760;   MESH:C098320
 xref: Beilstein:7387333;   CAS:154598-52-4;   DrugBank:DB00625;   Drug_Central:989;   HMDB:HMDB0014763;   KEGG:C08088;   KEGG:D00896;   LINCS:LSM-5526
 xref_mesh: MESH:C098320
 xref: PDBeChem:EFZ;   PMID:10576692;   PMID:10673109;   PMID:25017682;   Patent:EP582455;   Patent:US5519021;   Reaxys:7387333;   Wikipedia:Efavirenz


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efavirenz term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb11 ATP binding cassette subfamily B member 11 multiple interactions
decreases activity
ISO efavirenz inhibits the reaction [ABCB11 protein results in increased transport of Taurocholic Acid]
efavirenz results in decreased activity of ABCB11 protein
CTD PMID:24014644 NCBI chr 3:55,480,024...55,587,946
Ensembl chr 3:55,480,024...55,587,946
JBrowse link
G Adipoq adiponectin, C1Q and collagen domain containing decreases expression
decreases secretion
ISO efavirenz results in decreased expression of ADIPOQ mRNA
efavirenz results in decreased secretion of ADIPOQ protein
CTD PMID:21619898 NCBI chr11:81,330,845...81,344,488
Ensembl chr11:81,330,293...81,344,488
JBrowse link
G Alb albumin affects binding ISO efavirenz binds to ALB protein CTD PMID:15814459, PMID:16336266 NCBI chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
JBrowse link
G Bcl2l11 BCL2 like 11 increases response to substance
increases expression
ISO BCL2L11 protein results in increased susceptibility to efavirenz metabolite
efavirenz metabolite results in increased expression of BCL2L11 mRNA; efavirenz metabolite results in increased expression of BCL2L11 protein; efavirenz results in increased expression of BCL2L11 mRNA; efavirenz results in increased expression of BCL2L11 protein
CTD PMID:21958719 NCBI chr 3:120,726,906...120,764,192
Ensembl chr 3:120,726,906...120,764,192
JBrowse link
G Canx calnexin affects localization ISO efavirenz affects the localization of CANX protein CTD PMID:28940366 NCBI chr10:35,800,942...35,833,939
Ensembl chr10:35,800,942...35,833,861
JBrowse link
G Casp3 caspase 3 multiple interactions ISO efavirenz metabolite results in increased cleavage of and results in increased activity of CASP3 protein; efavirenz results in increased cleavage of and results in increased activity of CASP3 protein CTD PMID:21958719 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 increases secretion ISO efavirenz results in increased secretion of CCL2 protein CTD PMID:21619898 NCBI chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870
JBrowse link
G Cebpa CCAAT/enhancer binding protein alpha decreases expression ISO efavirenz results in decreased expression of CEBPA mRNA CTD PMID:21619898 NCBI chr 1:91,363,492...91,366,164
Ensembl chr 1:91,363,492...91,366,164
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 affects metabolic processing
decreases activity
multiple interactions
increases metabolic processing
ISO CYP2B6 gene polymorphism affects the metabolism of efavirenz; CYP2B6 protein affects the metabolism of efavirenz
efavirenz results in decreased activity of CYP2B6 protein
[efavirenz results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [efavirenz results in increased activity of NR1I3 protein alternative form] which results in increased expression of CYP2B6 mRNA; [efavirenz results in increased activity of NR1I3 protein] which results in increased expression of CYP2B6 mRNA
CYP2B6 protein results in increased metabolism of efavirenz
CTD PMID:15622315, PMID:15769884, PMID:17041008, PMID:17559344, PMID:26599973 NCBI chr 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 decreases activity ISO efavirenz results in decreased activity of CYP2C19 protein CTD PMID:11225565 NCBI chr 1:147,713,879...147,814,410
Ensembl chr 1:147,713,892...147,888,007
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO efavirenz results in increased expression of DDIT3 protein CTD PMID:28940366 NCBI chr 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
JBrowse link
G Dnm1l dynamin 1-like affects localization ISO efavirenz affects the localization of DNM1L protein modified form CTD PMID:28940366 NCBI chr11:88,830,968...88,882,271
Ensembl chr11:88,830,957...88,880,198
JBrowse link
G Eif2ak3 eukaryotic translation initiation factor 2 alpha kinase 3 increases expression ISO efavirenz results in increased expression of EIF2AK3 protein modified form CTD PMID:28940366 NCBI chr 4:98,648,513...98,709,695
Ensembl chr 4:98,648,545...98,709,694
JBrowse link
G Fis1 fission, mitochondrial 1 increases expression ISO efavirenz results in increased expression of FIS1 mRNA CTD PMID:28940366 NCBI chr12:22,750,485...22,765,324
Ensembl chr12:22,750,485...22,765,308
JBrowse link
G Hgf hepatocyte growth factor increases secretion ISO efavirenz results in increased secretion of HGF protein CTD PMID:21619898 NCBI chr 4:15,435,460...15,505,377
Ensembl chr 4:15,433,295...15,505,362
JBrowse link
G Hspa9 heat shock protein family A (Hsp70) member 9 multiple interactions ISO efavirenz promotes the reaction [VDAC1 protein binds to HSPA9 protein] CTD PMID:28940366 NCBI chr18:27,731,072...27,749,235
Ensembl chr18:27,731,072...27,749,235
JBrowse link
G Il6 interleukin 6 increases secretion ISO efavirenz results in increased secretion of IL6 protein CTD PMID:21619898 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit increases phosphorylation ISO efavirenz metabolite results in increased phosphorylation of JUN protein; efavirenz results in increased phosphorylation of JUN protein CTD PMID:21958719 NCBI chr 5:114,011,184...114,014,277
Ensembl chr 5:114,011,189...114,014,277
JBrowse link
G Lep leptin decreases expression ISO efavirenz results in decreased expression of LEP mRNA CTD PMID:21619898 NCBI chr 4:56,337,695...56,351,818
Ensembl chr 4:56,337,695...56,351,818
JBrowse link
G Lonp1 lon peptidase 1, mitochondrial multiple interactions
increases expression
increases response to substance
ISO efavirenz results in increased expression of and affects the localization of LONP1 protein; Mn(III) 5,10,15,20-tetrakis(N-methylpyridinium-2-yl)porphyrin inhibits the reaction [efavirenz results in increased expression of LONP1 mRNA]
LONP1 protein results in increased susceptibility to efavirenz
CTD PMID:28940366 NCBI chr 9:10,428,853...10,441,180
Ensembl chr 9:10,428,853...10,441,177
JBrowse link
G Lpl lipoprotein lipase decreases expression ISO efavirenz results in decreased expression of LPL mRNA CTD PMID:21619898 NCBI chr16:22,537,687...22,561,487
Ensembl chr16:22,537,056...22,561,496
JBrowse link
G Map3k5 mitogen-activated protein kinase kinase kinase 5 increases phosphorylation ISO efavirenz metabolite results in increased phosphorylation of MAP3K5 protein; efavirenz results in increased phosphorylation of MAP3K5 protein CTD PMID:21958719 NCBI chr 1:15,412,603...15,613,752
Ensembl chr 1:15,412,603...15,613,746
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions
increases phosphorylation
ISO Acetylcysteine inhibits the reaction [efavirenz metabolite results in increased phosphorylation of MAPK8 protein]; Acetylcysteine inhibits the reaction [efavirenz results in increased phosphorylation of MAPK8 protein]
efavirenz metabolite results in increased phosphorylation of MAPK8 protein; efavirenz results in increased phosphorylation of MAPK8 protein
CTD PMID:21958719 NCBI chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
JBrowse link
G Mfn2 mitofusin 2 increases expression ISO efavirenz results in increased expression of MFN2 mRNA CTD PMID:28940366 NCBI chr 5:164,684,244...164,715,414
Ensembl chr 5:164,684,509...164,714,145
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 increases activity EXP efavirenz results in increased activity of NR1I2 protein CTD PMID:27732639 NCBI chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
JBrowse link
G Nr1i3 nuclear receptor subfamily 1, group I, member 3 multiple interactions
increases activity
ISO
EXP
[efavirenz results in increased activity of NR1I3 protein alternative form] which results in increased expression of CYP2B6 mRNA; [efavirenz results in increased activity of NR1I3 protein] which results in increased expression of CYP2B6 mRNA CTD PMID:17041008, PMID:27732639 NCBI chr13:89,585,072...89,591,278
Ensembl chr13:89,586,283...89,591,277
JBrowse link
G Opa1 OPA1, mitochondrial dynamin like GTPase increases expression ISO efavirenz results in increased expression of OPA1 mRNA CTD PMID:28940366 NCBI chr11:74,717,600...74,793,902
Ensembl chr11:74,720,254...74,793,803
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma decreases expression ISO efavirenz results in decreased expression of PPARG mRNA CTD PMID:21619898 NCBI chr 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
JBrowse link
G Rmdn3 regulator of microtubule dynamics 3 increases expression ISO efavirenz results in increased expression of RMDN3 protein CTD PMID:28940366 NCBI chr 3:110,943,843...110,964,449
Ensembl chr 3:110,943,826...110,964,452
JBrowse link
G Serpine1 serpin family E member 1 increases secretion ISO efavirenz results in increased secretion of SERPINE1 protein CTD PMID:21619898 NCBI chr12:22,641,104...22,651,482
Ensembl chr12:22,641,104...22,651,482
JBrowse link
G Slc5a5 solute carrier family 5 member 5 multiple interactions ISO [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 mRNA; [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 protein CTD PMID:16030158 NCBI chr16:20,297,414...20,307,401
Ensembl chr16:20,297,414...20,307,400
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 decreases expression ISO efavirenz results in decreased expression of SREBF1 mRNA CTD PMID:21619898 NCBI chr10:46,570,996...46,593,021
Ensembl chr10:46,570,996...46,593,009
JBrowse link
G Tg thyroglobulin increases expression ISO efavirenz results in increased expression of TG mRNA; efavirenz results in increased expression of TG protein CTD PMID:16030158 NCBI chr 7:107,467,260...107,652,897
Ensembl chr 7:107,467,260...107,652,899
JBrowse link
G Tpo thyroid peroxidase increases expression ISO efavirenz results in increased expression of TPO mRNA; efavirenz results in increased expression of TPO protein CTD PMID:16030158 NCBI chr 6:49,020,918...49,089,855
Ensembl chr 6:49,021,044...49,089,855
JBrowse link
G Tshb thyroid stimulating hormone subunit beta multiple interactions ISO [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 mRNA; [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 protein; efavirenz promotes the reaction [TSHB protein affects the abundance of Iodine]; sodium perchlorate inhibits the reaction [efavirenz promotes the reaction [TSHB protein affects the abundance of Iodine]] CTD PMID:16030158 NCBI chr 2:205,207,799...205,215,199
Ensembl chr 2:205,207,799...205,212,681
JBrowse link
G Tshr thyroid stimulating hormone receptor increases expression ISO efavirenz results in increased expression of TSHR mRNA CTD PMID:16030158 NCBI chr 6:115,170,290...115,306,871
Ensembl chr 6:115,170,865...115,306,871
JBrowse link
G Vdac1 voltage-dependent anion channel 1 multiple interactions ISO efavirenz promotes the reaction [VDAC1 protein binds to HSPA9 protein] CTD PMID:28940366 NCBI chr10:37,724,915...37,752,827
Ensembl chr10:37,724,915...37,752,826
JBrowse link

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  CHEBI ontology 19770
    role 19718
      biological role 19717
        antimicrobial agent 17297
          antiviral agent 10245
            antiviral drug 1822
              efavirenz 37
Path 2
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  CHEBI ontology 19770
    subatomic particle 19768
      composite particle 19768
        hadron 19768
          baryon 19768
            nucleon 19768
              atomic nucleus 19768
                atom 19768
                  main group element atom 19655
                    p-block element atom 19655
                      carbon group element atom 19550
                        carbon atom 19539
                          organic molecular entity 19539
                            organic molecule 19461
                              organic cyclic compound 19232
                                organic heterocyclic compound 18404
                                  organic heteropolycyclic compound 17812
                                    organic heterobicyclic compound 16739
                                      benzoxazine 41
                                        efavirenz 37
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.