Palmatine - analytical standard, Moligand™, ≥97% , CAS No.3486-67-7

CAS: 3486-67-7 Cat. No.: P111383 Molecular Weight: 352.4

GRADE & PURITY Analytical standard, Moligand™, ≥97%

Synonyms

KBio2_007496 | PALMITINE | 7,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxyberbinium | KBio1_001659 | KBio3_001854 | Palmatine-chloride | KBioGR_001469 | PALMATINE (NEGATIVE MARKER) (CONSTITUENT OF GOLDENSEAL) | 5-21-06-00202 (Beilstein Handbook Reference) | K

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

Palmatine is an orally active and irreversible indoleamine 2,3-dioxygenase 1 (IDO-1) inhibitor with IC50s of 3 μM and 157μM against HEK 293-hIDO-1 and rhIDO-1, respectively. Palmatine can also inhibit West Nile virus (WNV) NS2B-NS3 protease in an uncompetitive manner with an IC50 of 96 μM. Palmatine shows anti-cancer, anti-oxidation, anti-inflammatory, neuroprotection, antibacterial, anti-viral activities

Specifications

Synonyms

KBio2_007496 | PALMITINE | 7, 8, 13, 13a-Tetrahydro-2, 3, 9, 10-tetramethoxyberbinium | KBio1_001659 | KBio3_001854 | Palmatine-chloride | KBioGR_001469 | PALMATINE (NEGATIVE MARKER) (CONSTITUENT OF GOLDENSEAL) | 5-21-06-00202 (Beilstein Handbook Reference) | K

Specifications & Purity

analytical standard, Moligand™, ≥97%

Storage

Protected from light, Room temperature

Shipped In

Normal

Grade

Analytical standard, Moligand™

Purity

≥97%

Names and Identifiers

• Canonical Smiles: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC
• IUPAC Name: 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
• InChIKey: QUCQEUCGKKTEBI-UHFFFAOYSA-N
• INCHI: 1S/C21H22NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,9-12H,7-8H2,1-4H3/q+1
• Isomeric SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC
• Molecular Weight: 352.4
• Reaxy-Rn: 1555498
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1555498&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Protoberberine alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Protoberberine alkaloids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Protoberberine alkaloids and derivatives
• Alternative Parents: Isoquinolines and derivatives Anisoles Alkyl aryl ethers Pyridinium derivatives Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Protoberberine skeleton - Isoquinoline - Anisole - Alkyl aryl ether - Pyridine - Pyridinium - Benzenoid - Heteroaromatic compound - Ether - Organoheterocyclic compound - Azacycle - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic cation - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
• External Descriptors: a small molecule

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

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Molecular Weight: 352.400 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 352.155 Da
• Monoisotopic Mass: 352.155 Da
• Topological Polar Surface Area: 40.800 Ų
• Heavy Atom Count: 26
• Formal Charge: 1
• Complexity: 475.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

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