Basic information
- CAS
102121-60-8- Standard SMILES
CC1(C)CCC(C)(C)c2cc(C(=O)Nc3ccc(C(=O)O)cc3)ccc21- InChIKey
SZWKGOZKRMMLAJ-UHFFFAOYSA-N- Molecular formula
- C22H25NO3
- Average molar mass
- 351.4 g/mol
- Monoisotopic mass
- 351.18344366
Overview
4-{[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acid is an amidobenzoic acid obtained by formal condensation of the carboxy group of (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzoic acid with the anilino group of 4-aminobenzoic acid. A selective RARalpha agonist. It has a role as an antineoplastic agent and a retinoic acid receptor alpha/beta agonist. It is a member of tetralins and an amidobenzoic acid.
Names & identifiers
- Preferred name
- Ro 40-6055
- IUPAC
- 4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acid
- English name
- 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acid
- Molecular formula
- C22H25NO3
- Molecular weight
- 351.44
Names & synonyms
Ro 40-60554-((5,5,8,8-tetramethyl6,7-dihydronaphthalene-2-carbonyl)amino)benzoic acid4-[(5,5,8,8-tetramethyl6,7-dihydronaphthalene-2-carbonyl)amino]benzoic acidRefChem:930825102121-60-8AM580Am 580AM-5804-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamido)benzoic acidCD-3364-{[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acidCD 336
Show more names
cd336CS-1051l)amino-ro40-6055MCE AM580NSC 608001AM580 (CD336)AM580, 10 mM in DMSOAM580, RARalpha agonists
DTXSID5040758MFCD006739164-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acidNSC608001VZ5S5G9ZFZCHEMBL693674-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acidBenzoic acid, 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]-
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 546
Experimental & physicochemical properties
Collision Cross Section198.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID5040758]
Physicochemical properties
- Melting point
- 265 · 265-267℃
- Boiling point
- 485.24 °C · 485.24°C (rough estimate)
- Density
- 1.154 · 1.154
- refractive index
- 1.5614 · 1.5614 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO (20mg/ml) or ethanol (10mg/ml).
- form
- White to off-white solid.
- pka
- 4.28 · 4.28±0.10(Predicted)
- color
- Off-white
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- InChI
- 1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- DH6834890
- hs_code
- 2924.29.7790
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
An agent that causes the production of physical defects in the developing embryo.
Applications
DescriptionAM-580 (102121-60-8) is a retinoic acid analog acting as a RARα agonist (Kd = 8 nM).1 Induces or blocks differentiation depending on cell type and environment.2,3 In combination with CHIR-99021 it induces differentiation of human induced pluripotent stem cells (iPSCs) into intermediate mesoderm (80% induction rate in 5 days) capable of forming kidney structures.4 AM-580 exhibits anti-angiogenic activity in vivo, and induces differentiation of acute promyelocytic leukemia cells.5,6
UsesRetinoid derivative used for gene expression studies of leukemia-retinoic acid receptor (PHL-RAR) cell line differentiation. AM 580 inhibits tumor proliferation by reducing the level of RARγ and activates RAR β. This receptor increases the expression of disintegrin and metalloprotease.
General DescriptionAM580 is a retinobenzoic derivative and a RAR-α (retinoic acid receptor-α) agonist. It stimulates the maturation of granulocytes in NB4 promyelocytic leukemia cell line and APL (acute promyelocytic leukemia) blasts. AM580 suppresses endometrial cancer cell proliferation.
Upstream & downstream products
Upstream raw materials
Related reactions
4 records
Compound notes
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