(3S,5S) -Atorvastatin

CAT: 0804-HY-B0589C-01Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-B0589C-01Size:5 mg

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Description

(3S,5S) -Atorvastatin is a inactive enantiomer of Atorvastatin. (3S,5S) -Atorvastatin can activate pregnane X receptor (PXR) . Atorvastatin is an orally active HMG-CoA reductase inhibitor, has the ability to effectively decrease blood lipids[1][2].

CAS Number

501121-34-2

UNSPSC

12352005

Hazard Statement

H302, H312, H332

Target

Cytochrome P450

Type

Reference compound

Related Pathways

Metabolic Enzyme/Protease

Applications

Metabolism-sugar/lipid metabolism

Field of Research

Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/3s-5s-atorvastatin.html

Concentration

10mM

Purity

95.0

Solubility

DMSO : 125 mg/mL (ultrasonic)

Smiles

O=C(C(C(C1=CC=CC=C1)=C(C2=CC=C(F)C=C2)N3CC[C@H](O)C[C@H](O)CC(O)=O)=C3C(C)C)NC4=CC=CC=C4

Molecular Formula

C33H35FN2O5

Molecular Weight

558.64

Precautions

H302, H312, H332

References & Citations

[1]Thomas A Kocarek, et al. Regulation of CYP2B6 and CYP3A Expression by Hydroxymethylglutaryl Coenzyme A Inhibitors in Primary Cultured Human Hepatocytes. Drug Metab Dispos. 2002 Dec;30 (12) :1400-5.|[2]Martina Korhonova, et al. Optical Isomers of Atorvastatin, Rosuvastatin and Fluvastatin Enantiospecifically Activate Pregnane X Receptor PXR and Induce CYP2A6, CYP2B6 and CYP3A4 in Human Hepatocytes. PLoS One. 2015 Sep 14;10 (9) :e0137720.|[3]Elena G Shcherbakova , et al. High-Throughput Assay for Enantiomeric Excess Determination in 1,2- And 1,3-Diols and Direct Asymmetric Reaction Screening. Chemistry. 2017 Jul 26;23 (42) :10222-10229.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Isoform

CYP2; CYP3

Chemical Information

ent-Atorvastatin

See also: Atorvastatin (annotation moved to).

CAS Number	501121-34-2
PubChem CID	62976
IUPAC Name	(3S,5S)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
Molecular Formula	C33H35FN2O5
Molecular Weight	558.6
XLogP	5
Topological Polar Surface Area	112
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	12
Heavy Atom Count	41
Formal Charge	0
Complexity	822

SMILES

CC(C)C1=C(C(=C(N1CC[C@@H](C[C@@H](CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4

InChI

InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m0/s1

InChIKey

XUKUURHRXDUEBC-SVBPBHIXSA-N

Chemical Structure

2D Structure

CAS: 501121-34-2

CID: 62976

Formula: C33H35FN2O5

MW: 558.6

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	558.6
XLogP3	5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	12
Exact Mass	558.25300038
Monoisotopic Mass	558.25300038
Topological Polar Surface Area	112 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	822
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Alternative Products

Catalog	Name
GTR19201909-01	(3S,5S) -Atorvastatin
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002937-01	(3S,5S) -Atorvastatin Sodium Salt
428103-01	(3S,5S) -Atorvastatin (Sodium Salt)
TRC-A791735-25MG	(3S,5S)-Atorvastatin Sodium Salt
TRC-A791755-10MG	(3S,5S)-Atorvastatin Calcium Salt
160927	(3S,5S) -Atorvastatin Calcium Salt
AR-A07315-01	(3S,5S) -Atorvastatin tert-Butyl Ester
259718-01	(3S,5S) -Atorvastatin acetonide tert-butyl ester
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(3S,5S) -Atorvastatin

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