4'-Demethylpodophyllotoxin - ≥98% , CAS No.40505-27-9

CAS: 40505-27-9 Cat. No.: D413075 Molecular Weight: 400.38

GRADE & PURITY ≥98%

Synonyms

AS-58706 | FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 5,8,8A,9-TETRAHYDRO-9-HYDROXY-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (5R,5AR,8AR,9R)- | UNII-7N5E50463V | s3908 | SCHEMBL12278154 | Q27105499 | AC-34637 | 7N5E50463V | CHEBI:1730 | DTXSID2013117

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

4'-Demethylpodophyllotoxin is isolated from the herb of Dysosma pleiantha (Hance) Woodson with remarkable cytotoxic potential in diverse cancer cell lines.

In vivo

The mean pharmacokinetic parameters of 4\'-Demethylpodophyllotoxin after oral administration of 367 mg/kg Diphylleia sinensis extract: Cmax=42.4 ± 14.6 ng/ml, Tmax= 1.60 ± 0.92 h, T_1/2z=3.35 ± 0.85 h, AUC_(0-t)=262 ± 122 ng·h/ml and AUC_(0-∞)=301 ± 129 ng·h/ml.

Specifications

Synonyms

AS-58706 | FURO(3', 4':6, 7)NAPHTHO(2, 3-D)-1, 3-DIOXOL-6(5AH)-ONE, 5, 8, 8A, 9-TETRAHYDRO-9-HYDROXY-5-(4-HYDROXY-3, 5-DIMETHOXYPHENYL)-, (5R, 5AR, 8AR, 9R)- | UNII-7N5E50463V | s3908 | SCHEMBL12278154 | Q27105499 | AC-34637 | 7N5E50463V | CHEBI:1730 | DTXSID2013117

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

4'-Demethylpodophyllotoxin is isolated from the herb of Dysosma pleiantha (Hance) Woodson with remarkable cytotoxic potential in diverse cancer cell lines.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Product Properties

• ALogP: 1.886
• hba_count: 6
• HBD Count: 2
• Rotatable Bond: 3

Names and Identifiers

• Pubchem Sid: 504756876
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756876
• Canonical Smiles: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• IUPAC Name: (5R,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-BTINSWFASA-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
• Isomeric 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
• Molecular Weight: 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
    • Class Lignan lactones
      • Subclass Podophyllotoxins

• Kingdom: Organic compounds
• Superclass: Lignans, neolignans and related compounds
• Class: 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
• Description: 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: Lignans

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

Associated Targets(Human)

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

PC-3 (62116 Activities)

Explore this target

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

GLC4 cell line (37 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

LNCaP (8286 Activities)

Explore this target

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

Associated Targets(non-human)

pol Human immunodeficiency virus type 1 integrase (9041 Activities)

Discover Target: pol

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

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

Vesicular stomatitis virus (4460 Activities)

Explore this target

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

P388 (20296 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 80 mg/mL (199.81 mM)
• DMSO(mg / mL) Max Solubility: 80
• DMSO(mM) Max Solubility: 199.8101803
• Molecular Weight: 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