| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| October 6th, 2004 | 26 | Yes |
Popular Name: BEXAROTENE BEXAROTENE
Find On: PubMed — Wikipedia — Google
CAS Numbers: 153559-49-0 , 166175-31-1
153559-49-0; Bexarotene (USAN/INN); D03106; Targretin (TN)
4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl)benzoic acid
4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid
4-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic acid
4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid
4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid; (for R&D only)
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl]benzoic acid
4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
4-[1-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthaleneyl)vinyl]benzene carboxylic acid
Benzoic acid, 4-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)-
bexarotene; bexaroteno; bexarotenum
LG-100069; LG100069; LGD-1069; LGD1069
p-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | 6.81 | 14.56 | -49.33 | 0 | 2 | -1 | 40 | 347.478 | 3 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| ALOGPS_SOLUBILITY | 1.49e-04 g/l | DrugBank-approved |
| Purity | 95% | Fluorochem |
| Purity | >99% | Fluorochem |
| Indications | cutaneous T-cell lymphoma | KeyOrganics Bioactives |
| Target | Others | Selleck Chemicals |
| Target | Retinoid Receptor | Selleck Chemicals |
| Patent Database Links | US2004131648; US2005014759; US2005014810; US2005137213; US2006035945; US2007185069; US2007190102; US2007208044; US2007213305; US2007213382; US2007244114; US2007249601; US2007249647; US2007249713; US2007253957; US2008096848; US2008214545; US2008261978; US2 | ChEBI |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| RARA-1-E | Retinoic Acid Receptor Alpha (cluster #1 Of 1), Eukaryotic | Eukaryotes | 5453 | 0.28 | Binding ≤ 10μM |
| RARB-1-E | Retinoic Acid Receptor Beta (cluster #1 Of 2), Eukaryotic | Eukaryotes | 5353 | 0.28 | Binding ≤ 10μM |
| RARG-1-E | Retinoic Acid Receptor Gamma (cluster #1 Of 2), Eukaryotic | Eukaryotes | 3206 | 0.30 | Binding ≤ 10μM |
| RXRA-1-E | Retinoid X Receptor Alpha (cluster #1 Of 1), Eukaryotic | Eukaryotes | 40 | 0.40 | Binding ≤ 10μM |
| RXRB-1-E | Retinoid X Receptor Beta (cluster #1 Of 2), Eukaryotic | Eukaryotes | 25 | 0.41 | Binding ≤ 10μM |
| RXRG-1-E | Retinoid X Receptor Gamma (cluster #1 Of 1), Eukaryotic | Eukaryotes | 8 | 0.44 | Binding ≤ 10μM |
| RARA-1-E | Retinoic Acid Receptor Alpha (cluster #1 Of 1), Eukaryotic | Eukaryotes | 6 | 0.44 | Functional ≤ 10μM |
| RARB-1-E | Retinoic Acid Receptor Beta (cluster #1 Of 1), Eukaryotic | Eukaryotes | 282 | 0.35 | Functional ≤ 10μM |
| RARG-1-E | Retinoic Acid Receptor Gamma (cluster #1 Of 1), Eukaryotic | Eukaryotes | 648 | 0.33 | Functional ≤ 10μM |
| RXRA-1-E | Retinoid X Receptor Alpha (cluster #1 Of 1), Eukaryotic | Eukaryotes | 52 | 0.39 | Functional ≤ 10μM |
| RXRB-1-E | Retinoid X Receptor Beta (cluster #1 Of 1), Eukaryotic | Eukaryotes | 25 | 0.41 | Functional ≤ 10μM |
| RXRG-1-E | Retinoid X Receptor Gamma (cluster #1 Of 2), Eukaryotic | Eukaryotes | 25 | 0.41 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| RARA_HUMAN | P10276 | Retinoic Acid Receptor Alpha, Human | 180 | 0.36 | Binding ≤ 1μM |
| RARB_HUMAN | P10826 | Retinoic Acid Receptor Beta, Human | 50 | 0.39 | Binding ≤ 1μM |
| RARG_HUMAN | P13631 | Retinoic Acid Receptor Gamma, Human | 130 | 0.37 | Binding ≤ 1μM |
| RXRA_MOUSE | P28700 | Retinoid X Receptor Alpha, Mouse | 40 | 0.40 | Binding ≤ 1μM |
| RXRA_HUMAN | P19793 | Retinoid X Receptor Alpha, Human | 14 | 0.42 | Binding ≤ 1μM |
| RXRB_MOUSE | P28704 | Retinoid X Receptor Beta, Mouse | 21 | 0.41 | Binding ≤ 1μM |
| RXRB_HUMAN | P28702 | Retinoid X Receptor Beta, Human | 112 | 0.37 | Binding ≤ 1μM |
| RXRG_HUMAN | P48443 | Retinoid X Receptor Gamma, Human | 122 | 0.37 | Binding ≤ 1μM |
| RXRG_MOUSE | P28705 | Retinoid X Receptor Gamma, Mouse | 20 | 0.41 | Binding ≤ 1μM |
| RARA_HUMAN | P10276 | Retinoic Acid Receptor Alpha, Human | 180 | 0.36 | Binding ≤ 10μM |
| RARB_HUMAN | P10826 | Retinoic Acid Receptor Beta, Human | 50 | 0.39 | Binding ≤ 10μM |
| RARG_HUMAN | P13631 | Retinoic Acid Receptor Gamma, Human | 130 | 0.37 | Binding ≤ 10μM |
| RXRA_MOUSE | P28700 | Retinoid X Receptor Alpha, Mouse | 40 | 0.40 | Binding ≤ 10μM |
| RXRA_HUMAN | P19793 | Retinoid X Receptor Alpha, Human | 14 | 0.42 | Binding ≤ 10μM |
| RXRB_MOUSE | P28704 | Retinoid X Receptor Beta, Mouse | 21 | 0.41 | Binding ≤ 10μM |
| RXRB_HUMAN | P28702 | Retinoid X Receptor Beta, Human | 112 | 0.37 | Binding ≤ 10μM |
| RXRG_HUMAN | P48443 | Retinoid X Receptor Gamma, Human | 122 | 0.37 | Binding ≤ 10μM |
| RXRG_MOUSE | P28705 | Retinoid X Receptor Gamma, Mouse | 20 | 0.41 | Binding ≤ 10μM |
| RARA_HUMAN | P10276 | Retinoic Acid Receptor Alpha, Human | 6 | 0.44 | Functional ≤ 10μM |
| RARB_HUMAN | P10826 | Retinoic Acid Receptor Beta, Human | 282 | 0.35 | Functional ≤ 10μM |
| RARG_HUMAN | P13631 | Retinoic Acid Receptor Gamma, Human | 648 | 0.33 | Functional ≤ 10μM |
| RXRA_HUMAN | P19793 | Retinoid X Receptor Alpha, Human | 19.8 | 0.41 | Functional ≤ 10μM |
| RXRB_MOUSE | P28704 | Retinoid X Receptor Beta, Mouse | 25 | 0.41 | Functional ≤ 10μM |
| RXRB_HUMAN | P28702 | Retinoid X Receptor Beta, Human | 24 | 0.41 | Functional ≤ 10μM |
| RXRG_HUMAN | P48443 | Retinoid X Receptor Gamma, Human | 20 | 0.41 | Functional ≤ 10μM |
| Description | Species |
|---|---|
| Activation of gene expression by SREBF (SREBP) | |
| BMAL1:CLOCK,NPAS2 activates circadian gene expression | |
| Circadian Clock | |
| Endogenous sterols | |
| Import of palmitoyl-CoA into the mitochondrial matrix | |
| Nuclear Receptor transcription pathway | |
| PPARA activates gene expression | |
| Recycling of bile acids and salts | |
| Regulation of lipid metabolism by Peroxisome proliferator-activated receptor alp | |
| Regulation of pyruvate dehydrogenase (PDH) complex | |
| REV-ERBA represses gene expression | |
| RORA activates circadian gene expression | |
| Synthesis of bile acids and bile salts | |
| Synthesis of bile acids and bile salts via 27-hydroxycholesterol | |
| Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol | |
| Transcriptional activation of mitochondrial biogenesis | |
| Transcriptional Regulation of Adipocyte Differentiation in 3T3-L1 Pre-adipocytes | |
| Transcriptional regulation of white adipocyte differentiation | |
| YAP1- and WWTR1 (TAZ)-stimulated gene expression |
