Pyripyropene A(PPPA) - Moligand™, ≥95% , CAS No.147444-03-9

CAS: 147444-03-9 Cat. No.: P275044 Molecular Weight: 583.63 EC Number: 813-163-5 PubChem CID: 11828024

GRADE & PURITY Moligand™, ≥95%

Synonyms

AKOS027320855 | CHEBI:64695 | NCGC00180218-02! | 7T8 | ACon1_001711 | Pyripyropene A | (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[(acetyloxy)methyl]-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-naphtho[2,1-b]p

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Product Describtion:

Pyripyropene A is a potent and selective sterol O-acyltransferase 2 (SOAT2)/acyl-coenzyme A:cholesterol acyltransferase 2 (ACAT2) inhibitor, with an IC50 of 0.07 µM. Pyripyropene A attenuates hypercholesterolemia and atherosclerosis in vivo.

Specifications

Synonyms

AKOS027320855 | CHEBI:64695 | NCGC00180218-02! | 7T8 | ACon1_001711 | Pyripyropene A | (3S, 4R, 4aR, 6S, 6aS, 12R, 12aS, 12bS)-4-[(acetyloxy)methyl]-12-hydroxy-4, 6a, 12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1, 3, 4, 4a, 5, 6, 6a, 12, 12a, 12b-decahydro-2H, 11H-naphtho[2, 1-b]p

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Highly potent and selective ACAT2 inhibitor (IC50 = 70 nm). It showed anti hypercholesterolemia and anti atherosclerosis effects in vivo.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Note

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.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC(=O)OCC1(C(CCC2(C1CC(C3(C2C(C4=C(O3)C=C(OC4=O)C5=CN=CC=C5)O)C)OC(=O)C)C)OC(=O)C)C
• IUPAC Name: [(1S,2S,5S,6R,7R,9S,10S,18R)-5,9-diacetyloxy-18-hydroxy-2,6,10-trimethyl-16-oxo-14-pyridin-3-yl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-6-yl]methyl acetate
• InChIKey: PMMQOFWSZRQWEV-RVTXXDJVSA-N
• INCHI: 1S/C31H37NO10/c1-16(33)38-15-30(5)22-13-24(40-18(3)35)31(6)27(29(22,4)10-9-23(30)39-17(2)34)26(36)25-21(42-31)12-20(41-28(25)37)19-8-7-11-32-14-19/h7-8,11-12,14,22-24,26-27,36H,9-10,13,15H2,1-6H3/t22-,23+,24+,26+,27-,29+,30+,31-/m1/s1
• Isomeric SMILES: CC(=O)OC[C@@]1([C@H](CC[C@]2([C@H]1C[C@@H]([C@@]3([C@@H]2[C@H](C4=C(O3)C=C(OC4=O)C5=CN=CC=C5)O)C)OC(=O)C)C)OC(=O)C)C
• PubChem CID: 11828024
• Molecular Weight: 583.63

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Hydroxysteroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Hydroxysteroids
• Intermediate Tree Nodes: Not available
• Direct Parent: 1-hydroxysteroids
• Alternative Parents: Naphthopyrans Naphthalenes Tricarboxylic acids and derivatives Alkyl aryl ethers Pyranones and derivatives Pyridines and derivatives Vinylogous esters Heteroaromatic compounds Secondary alcohols Lactones Carboxylic acid esters Oxacyclic compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 1-hydroxysteroid - Naphthopyran - Naphthalene - Tricarboxylic acid or derivatives - Alkyl aryl ether - Pyranone - Pyran - Pyridine - Heteroaromatic compound - Vinylogous ester - Secondary alcohol - Carboxylic acid ester - Lactone - Azacycle - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Ether - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-hydroxysteroids. These are steroids carrying a hydroxyl group at the 1-position of the steroid backbone.
• External Descriptors: organic heterotetracyclic compound - sesquiterpenoid

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)

SOAT2 Tchem Sterol O-acyltransferase 2 (2 Activities)

Discover Target: SOAT2

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

SOAT2 Tchem Acyl coenzyme A:cholesterol acyltransferase 2 (288 Activities)

Discover Target: SOAT2

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

Associated Targets(non-human)

Soat1 Acyl coenzyme A:cholesterol acyltransferase 1 (295 Activities)

Discover Target: Soat1

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO and Methanol
• Molecular Weight: 583.600 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 583.242 Da
• Monoisotopic Mass: 583.242 Da
• Topological Polar Surface Area: 148.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 1230.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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