Isotretinoína - Moligand™, ≥98% , Retinoic acid receptor agonist, CAS No.4759-48-2, Retinoic acid receptor agonist

CAS: 4759-48-2 Cat. No.: I129856 Peso molecular: 300.44 Beilstein Registry Number: 9(4)2388 Número EC: 225-296-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

13 Ácido cisretinoico | HSDB 3929 | ISOTRETINOÍNA [MI] | BSPBio_000072 | Isosuprea Lidose | Roacutan | isotretinoína | Ro-43780 | Ro-4-3780 | Ácido 2-cis-vitamina A | ISOTRETINOÍNA (MONOGRÁFICO USP) | ISOTRETINOÍNA [MONOGRÁFICO EP] | Isotretinoína [INN-Fr

Storage

Almacenar a -20°C,cargado con argón

Shipped In

Hielera + almohadillas de hielo

Descripción general

Análogo de la vitamina A que inhibe la proliferación celular.

el ácido 13-cis-retinoico se ha utilizado

- como componente de medios frescos para la diferenciación de LA-N-5

- para tratar células de meduloblastoma para la diferenciación celular

- en el tratamiento de esferoides para generar vídeos time-lapse

- para examinar su actividad deformadora de la cabeza en condiciones de luz y oscuridad en Xenopus laevis

Specifications

Sinónimos

13 Ácido cisretinoico | HSDB 3929 | ISOTRETINOÍNA [MI] | BSPBio_000072 | Isosuprea Lidose | Roacutan | isotretinoína | Ro-43780 | Ro-4-3780 | Ácido 2-cis-vitamina A | ISOTRETINOÍNA (MONOGRÁFICO USP) | ISOTRETINOÍNA [MONOGRÁFICO EP] | Isotretinoína [INN-Fr

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

el ácido 13-cis-retinoico es un análogo de la vitamina A que inhibe la proliferación celular e induce la diferenciación celular. el ácido 13-cis-retinoico (AR) tiene acción antiinflamatoria y antitumoral. La acción del AR está mediada por los receptores R

Condiciones de almacenamiento de almacenamiento

Almacenar a -20°C, cargado con argón

Enviado en

Hielera + almohadillas de hielo

Grado

Moligand™

Tipo de acción

AGONIST

Mecanismo de acción

Retinoic acid receptor agonist

Pureza

≥98%

Propiedades del producto

• ALogP: 6.3

Nombres e identificadores

• Pubchem Sid: 504763423
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763423
• Sonrisas canónicas: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
• IUPAC Name: (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• InChIKey: SHGAZHPCJJPHSC-XFYACQKRSA-N
• INCHI: 1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
• Isómeros SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C
• WGK Alemania: 3
• RTECS: VH6440000
• Peso molecular: 300.44
• Beilstein: 9(4)2388
• Reaxy-Rn: 2508066
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2508066&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Prenol lipids
      • Subclass Retinoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Prenol lipids
• Subclass: Retinoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Retinoids
• Alternative Parents: Diterpenoids Medium-chain fatty acids Methyl-branched fatty acids Unsaturated fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Retinoic acid - Diterpenoid - Retinoid skeleton - Medium-chain fatty acid - Branched fatty acid - Methyl-branched fatty acid - Fatty acyl - Unsaturated fatty acid - Fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
• External Descriptors: Retinoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

OR51E2 Tchem Olfactory receptor 51E2 (2 Activities)

Discover Target: OR51E2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

Discover Target: HMGCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

Discover Target: INSR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RARA Tclin Retinoic acid receptor alpha (1324 Activities)

Discover Target: RARA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

Discover Target: ACE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

Discover Target: DRD2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

Discover Target: GABRA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

Discover Target: CNR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

Discover Target: DRD4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH2 Tclin Histamine H2 receptor (5428 Activities)

Discover Target: HRH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

Discover Target: ADRA1D

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

Discover Target: HTR1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

Discover Target: HTR2C

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CALCR Tclin Calcitonin receptor (2215 Activities)

Discover Target: CALCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

Discover Target: HRH1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

Discover Target: ADRA1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

Discover Target: OPRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

Discover Target: AVPR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

Discover Target: OPRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRK1 Tclin Kappa opioid receptor (16155 Activities)

Discover Target: OPRK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

Discover Target: PTH1R

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

Discover Target: HTR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

Discover Target: PDE3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

Discover Target: Agtr2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc4r Melanocortin receptor 4 (1205 Activities)

Discover Target: Mc4r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ltc4s Leukotriene C4 synthase (1 Activities)

Discover Target: Ltc4s

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Sigmar1 Sigma opioid receptor (160 Activities)

Discover Target: Sigmar1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

Discover Target: Npy1r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cruzipain (33337 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cckar Cholecystokinin A receptor (90 Activities)

Discover Target: Cckar

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nos2 Nitric oxide synthase, inducible (3573 Activities)

Discover Target: Nos2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp9 Matrix metalloproteinase 9 (38 Activities)

Discover Target: Mmp9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pseudomonas aeruginosa (123386 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Klebsiella pneumoniae (43867 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cryptococcus neoformans (21258 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Candida albicans (78123 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cricetinae gen. sp. (3197 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F9 (77 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lef Anthrax lethal factor (7585 Activities)

Discover Target: lef

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Brain (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasma (328 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FTL Ferritin light chain (43324 Activities)

Discover Target: FTL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Glra2 Glycine receptor (1745 Activities)

Discover Target: Glra2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in chloroform (50 mg/ml), DMSO (60 mg/ml at 25 °C), water (<1 mg/ml at 25 °C), ethanol (25 mg/ml), and ether (sparingly).
• Sensibilidad: air sensitive ;light sensitive;heat sensitive
• Punto de fusión (°C): 175°C
• Peso molecular: 300.400 g/mol
• XLogP3: 6.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 300.209 Da
• Monoisotopic Mass: 300.209 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 567.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1

Referencias

1. Peng Zhang, Lei Tian, Jiayu Bao, Shang Li, Ao Li, Ya Wen, Jingyi Wang, Ying Jie.  (2022)  Isotretinoin Impairs the Secretory Function of Meibomian Gland Via the PPARγ Signaling Pathway.  INVESTIGATIVE OPHTHALMOLOGY & VISUAL SCIENCE,  63  (3): (29-29).  [PMID:35353124] [10.1167/iovs.63.3.29]

2. Shungen Huang, Xian Yang, Yajuan Gao, Haoying Huang, Tuanwei Li, Meng Li, Feng Wu, Hongcao Yang, Chunyan Li.  (2024)  Multifunctional nano co-delivery system for efficiently eliminating neuroblastoma by overcoming cancer heterogeneity.  Biomedical Materials,  19  (6): (065033).  [PMID:39419089] [10.1088/1748-605X/ad8826]

3. Jinshuang Wang, Qin Ye, Ningxiang Yu, Weiwei Huan, Jingliang Sun, Xiaohua Nie, Xianghe Meng.  (2021)  Preparation of multiresponsive hydrophilic molecularly imprinted microspheres for rapid separation of gardenia yellow and geniposide from gardenia fruit.  FOOD CHEMISTRY,      [PMID:34823938] [10.1016/j.foodchem.2021.131610]