Schisantherin A - Analytical standard, Moligand™, ≥98% , CAS No.58546-56-8

CAS: 58546-56-8 Cat. No.: S117970 Molecular Weight: 536.57 PubChem CID: 151529

GRADE & PURITY Analytical standard, Moligand™, ≥98%

Synonyms

MFCD09026937 | NCI60_003686 | SCHISANTHERIN A (GOMISIN C) (CONSTITUENT OF NORTHERN SCHISANDRA) [DSC] | WLN: QY5&1 | Schisantherin A | (5S,6S,7S)-6-hydroxy-1,2,3,13-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

MFCD09026937 | NCI60_003686 | SCHISANTHERIN A (GOMISIN C) (CONSTITUENT OF NORTHERN SCHISANDRA) [DSC] | WLN: QY5&1 | Schisantherin A | (5S, 6S, 7S)-6-hydroxy-1, 2, 3, 13-tetramethoxy-6, 7-dimethyl-5, 6, 7, 8-tetrahydrobenzo[3', 4']cycloocta[1', 2':4, 5]benzo[1, 2-d][1,

Specifications & Purity

Analytical standard, Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Schisantherin A is a lignan isolated from the fruits of Schisandra chinesi. Schisantherin A is a mechanism-based inhibitor that competitively inhibits and irreversibly inactivates CYP3A4.

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Analytical standard, Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4C(C1(C)O)OC(=O)C5=CC=CC=C5)OC)OC)OC)OC)OCO3
• IUPAC Name: [(8S,9S,10S)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl] benzoate
• InChIKey: UFCGDBKFOKKVAC-DSASHONVSA-N
• INCHI: 1S/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3/t16-,28-,30-/m0/s1
• Isomeric SMILES: C[C@H]1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4[C@@H]([C@@]1(C)O)OC(=O)C5=CC=CC=C5)OC)OC)OC)OC)OCO3
• PubChem CID: 151529
• Molecular Weight: 536.57

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Tannins
      • Subclass Hydrolyzable tannins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Tannins
• Subclass: Hydrolyzable tannins
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydrolyzable tannins
• Alternative Parents: Dibenzocyclooctadiene lignans Benzoic acid esters Benzodioxoles Benzoyl derivatives Anisoles Alkyl aryl ethers Tertiary alcohols Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Acetals Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydrolyzable tannin - Dibenzocyclooctane lignan - Benzoate ester - Benzodioxole - Benzoic acid or derivatives - Anisole - Benzoyl - Alkyl aryl ether - Benzenoid - Monocyclic benzene moiety - Tertiary alcohol - Carboxylic acid ester - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Acetal - Ether - Carboxylic acid derivative - Organooxygen compound - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
• 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)

CYP3A4 Tclin Cytochrome P450 3A4 (1 Activities)

Discover Target: CYP3A4

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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

K562 (73714 Activities)

Explore this target

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

Raji (5516 Activities)

Explore this target

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

SiHa (2051 Activities)

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

SK-HEP1 (1155 Activities)

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

SNU-638 (372 Activities)

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

A549 (127892 Activities)

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

T47D (39041 Activities)

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

MDA-MB-231 (73002 Activities)

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

Associated Targets(non-human)

Rattus norvegicus (775804 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

• Sensitivity: Air sensitive;light sensitive,Heat sensitive
• Molecular Weight: 536.600 g/mol
• XLogP3: 5.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 536.205 Da
• Monoisotopic Mass: 536.205 Da
• Topological Polar Surface Area: 102.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 833.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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

References

1. Xiao-Hua Zhang, Hai-Long Wu, Xiao-Li Yin, Yong Li, Xiang-Dong Qing, Hui-Wen Gu, Chao Kang, Ru-Qin Yu.  (2016)  Exploiting third-order advantage using four-way calibration method for direct quantitative analysis of active ingredients of Schisandra chinensis in DMEM by processing four-way excitation–emission-solvent fluorescence data.  CHEMOMETRICS AND INTELLIGENT LABORATORY SYSTEMS,      [PMID:] [10.1016/j.chemolab.2016.04.008]

2. Cong Liu, Yun-Feng Cao, Zhong-Ze Fang, Yan-Yan Zhang, Cui-Min Hu, Xiao-Yu Sun, Ting Huang, Jia Zeng, Xu-Ran Fan, Mo Hong.  (2012)  Strong inhibition of deoxyschizandrin and schisantherin A toward UDP-glucuronosyltransferase (UGT) 1A3 indicating UGT inhibition-based herb–drug interaction.  FITOTERAPIA,      [PMID:23339253] [10.1016/j.fitote.2012.08.004]

3. Zhao Zijia, Gao Yan, Yuan Min, Ye Cai, Guo Yingxue, Zhao Yanli, Li Jinlian, Cui Jiwen, Dong Tianwei, Wu Dongmei.  (2024)  Application Prospects of Schisandra chinensis Fruit Post-Distillation Residues in Anti-Photoaging Products: Enhancing Anti-Photoaging Through Lignans Conversion.  Waste and Biomass Valorization,      [PMID:] [10.1007/s12649-024-02846-0]