4'-Demethylepipodophyllotoxin - ≥98% , CAS No.6559-91-7

CAS: 6559-91-7 Cat. No.: D276525 Peso molecular: 400.38 Número EC: 613-823-0

GRADE & PURITY ≥98%

Synonyms

(5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one | Tox21_113196 | 4'-O-demethylepipodophyllotoxin | A935071 | 4'-demethyl-9-epipodophyllotoxin | D5653 | CYANOCOBALAMIN COMPONENT

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Specifications

Sinónimos

(5S, 5aR, 8aR, 9R)-5-hydroxy-9-(4-hydroxy-3, 5-dimethoxy-phenyl)-5a, 6, 8a, 9-tetrahydro-5H-isobenzofuro[6, 5-f][1, 3]benzodioxol-8-one | Tox21_113196 | 4'-O-demethylepipodophyllotoxin | A935071 | 4'-demethyl-9-epipodophyllotoxin | D5653 | CYANOCOBALAMIN COMPONENT

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Antimitotic agent. Potent inhibitor of microtubule assembly. Antioxidant and chemopreventive effects in vivo. Orally active.

Condiciones de almacenamiento de almacenamiento

Store at -20°C, Desiccated

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488187688
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187688
• Sonrisas canónicas: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• IUPAC Name: (5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• InChIKey: YVCVYCSAAZQOJI-JHQYFNNDSA-N
• INCHI: 1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
• Isómeros SMILES: COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O
• Peso molecular: 400.38
• Reaxy-Rn: 365236
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=365236&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lignans, neolignans and related compounds
    • Clase Lignan lactones
      • Subclass Podophyllotoxins

• Kingdom: Organic compounds
• Superclass: Lignans, neolignans and related compounds
• Clase: Lignan lactones
• Subclass: Podophyllotoxins
• Intermediate Tree Nodes: Not available
• Direct Parent: Podophyllotoxins
• Alternative Parents: Aryltetralin lignans Furanonaphthodioxoles Tetralins Dimethoxybenzenes Methoxyphenols Benzodioxoles Anisoles Phenoxy compounds Alkyl aryl ethers Gamma butyrolactones Tetrahydrofurans Carboxylic acid esters Secondary alcohols Monocarboxylic acids and derivatives Oxacyclic compounds Acetals Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Podophyllotoxin - 1-aryltetralin lignan - Linear furanonaphthodioxole - Naphthofuran - Methoxyphenol - M-dimethoxybenzene - Dimethoxybenzene - Tetralin - Benzodioxole - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Alkyl aryl ether - Phenol - Benzenoid - Gamma butyrolactone - Monocyclic benzene moiety - Tetrahydrofuran - Lactone - Carboxylic acid ester - Secondary alcohol - Acetal - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Ether - Monocarboxylic acid or derivatives - Alcohol - Carbonyl group - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).
• External Descriptors: organic heterotetracyclic compound - phenols - furonaphthodioxole

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)

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

Discover Target: TOP2A

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

HL-60 (67320 Activities)

Explore this target

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

HT-1080 (3966 Activities)

Explore this target

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

HT-29 (80576 Activities)

Explore this target

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

MCF7 (126967 Activities)

Explore this target

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

MRC5 (9203 Activities)

Explore this target

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

A549 (127892 Activities)

Explore this target

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

H9 (1832 Activities)

Explore this target

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

HaCaT (4069 Activities)

Explore this target

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

HMEC (560 Activities)

Explore this target

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

HepG2 (196354 Activities)

Explore this target

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

KB (17409 Activities)

Explore this target

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

M21 (1715 Activities)

Explore this target

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

HeLa (62764 Activities)

Explore this target

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

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

Objetivos asociados (no humanos)

Top2 DNA topoisomerase II (15 Activities)

Discover Target: Top2

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

Human alphaherpesvirus 1 (11089 Activities)

Explore this target

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

Mythimna separata (3306 Activities)

Explore this target

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in DMSO (with warming)；Chloroform (Slightly), Methanol (Slightly)
• Sensibilidad: Heat Sensitive
• Rotación específica [α]: -68.0 to -60.0 deg(C=0.65, MeOH)
• Punto de fusión (°C): 220-225ºC
• Peso molecular: 400.400 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 400.116 Da
• Monoisotopic Mass: 400.116 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 614.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Xiang Zhou, Haojie Ye, Xiuhui Gao, Yumei Feng, Wubin Shao, Puying Qi, Zhibing Wu, Liwei Liu, Peiyi Wang, Song Yang.  (2021)  The discovery of natural 4'-demethylepipodophyllotoxin from renewable Dysosma versipellis species as a novel bacterial cell division inhibitor for controlling intractable diseases in rice.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2021.114182]