Basic information
- CAS
496868-77-0- Standard SMILES
O=C(O)/C=C/c1ccc(-c2ccc(O)c(C34CC5CC(CC(C5)C3)C4)c2)cc1- InChIKey
QAWBIEIZDDIEMW-FPYGCLRLSA-N- Molecular formula
- C25H26O3
- Average molar mass
- 374.5 g/mol
- Monoisotopic mass
- 374.18819469
Overview
Adarotene is a synthetic, phenolic hydroxyl retinoid with proapoptotic activity. As an atypical retinoid, adarotene has the ability to induce apoptosis which is independent of retinoid receptor signaling.
Names & identifiers
- Preferred name
- Adarotene
- IUPAC
- (E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid
- English name
- (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid
- Molecular formula
- C25H26O3
- Molecular weight
- 374.47
Names & synonyms
Adarotene496868-77-0W6SU73VG8H(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acidDTXSID9040390adarotenoadarotenum(2E)-3-(4'-Hydroxy-3'-tricyclo(3.3.1.13,7)dec-1-yl(1,1'-biphenyl)-4-yl)-2-propenoic acidRefChem:552953DTXCID7020390ST1926Adarotene [INN]
Show more names
Adarotene (ST1926)Adarotene, 10 mM in DMSOInhibitor,inhibit,Apoptosis,ST-1926,ST 1926,Adarotene
ST 1926CHEMBL442016(E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid(E)-3-(3'-((3r,5r,7r)-adamantan-1-yl)-4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylic acidUNII-W6SU73VG8HST-19262-Propenoic acid, 3-(4'-hydroxy-3'-tricyclo(3.3.1.13,7)dec-1-yl(1,1'-biphenyl)-4-yl)-, (2E)-2-Propenoic acid, 3-(4'-hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-, (2E)-
Database identifiers
- CAS
496868-77-0- PubChem CID
- 9864378
- DTXSID
Properties
Computed structural properties
- XLogP
- 6.5
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 574
Physicochemical properties
- Melting point
- 240 °C · >240 °C
- Boiling point
- 574.1 · 574.1±50.0 °C(Predicted)
- Density
- 1.257 · 1.257
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 37.4 mg/mL · ≥37.4 mg/mL in DMSO; insoluble in H2O; ≥10.97 mg/mL in EtOH with gentle warming and ultrasonic
- form
- solid
- pka
- -95.54 · -95.54±0.10(Predicted)
- color
- White to green
- InChI
- 1S/C25H26O3/c26-23-7-6-21(20-4-1-16(2-5-20)3-8-24(27)28)12-22(23)25-13-17-9-18(14-25)11-19(10-17)15-25/h1-8,12,17-19,26H,9-11,13-15H2,(H,27,28)/b8-3+
- InChIKey
- QAWBIEIZDDIEMW-FPYGCLRLSA-N
- SMILES
- Oc1c(cc(cc1)c5ccc(cc5)\C=C\C(=O)O)C32CC4CC(C3)CC(C2)C4
- FDA UNII
- 6 SU73VG8H · W6SU73VG8H
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Chemistry & industry
Applications
UsesAdarotene has been found to have antitumor activity against different types of cancer, including acute myeloid leukemia, primary effusion lymphoma, prostate cancer and glioma. It may also be useful in treating acute lung injury through inflammation and ROS suppression via inactivating TLR4/NF-κB and p38/ERK1/2 signaling pathways.
Upstream & downstream products
Upstream raw materials
Suppliers52 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
江苏艾康生物医药研发有限公司025-58851090 19370895928 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
Related reactions
1 records
Compound notes
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