Nigranoic acid - ≥95% , CAS No.39111-07-4

CAS: 39111-07-4 Cat. No.: N649415 Molecular Weight: 470.68 PubChem CID: 10814237

GRADE & PURITY ≥95%

Synonyms

DTXSID301319075 | Nigranoic acid | CHEBI:66626 | Q27135245 | HY-122935 | 3,4-Secocycloarta-4(28),24-(Z)-diene-3,26-dioic acid | (2Z,6R)-6-[(1R,3aS,3bS,6S,6aR,7aS,9aR)-6a-(2-carboxyethyl)-3a,9a-dimethyl-6-(prop-1-en-2-yl)dodecahydro-1H-cyclopenta[a]cyclopr

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Nigranoic acid is a triterpenoid separated from Schisandra chinensis . Nigranoic acid inhibits HIV-1 reverse transcriptase . Nigranoic acid exhibits protective effects on brain through PARP/AIF signaling pathway in cerebral ischemia-reperfusion animal model

In Vivo

Nigranoic acid has a strong protective effect on rat cerebral ischemia-reperfusion injury, and acts by downregulating nerve cell apoptosis by preventing the overactivation of PARP and AIF nuclear translocation. Nigranoic acid (1 mg/kg; i.g.; 6 hours and 2 hours before brain ischemia) significantly decreases apoptosis and the expression levels of AIF protein, PARP protein, and AIF mRNA at different time-points. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Sprague–Dawley rats (200-300 g), ischemia–reperfusion modelDosage: 1 mg/kg Administration: Intragastric; 6 hours and 2 hours before brain ischemia Result: Decreased apoptosis and the expression levels of AIF protein, PARP protein, and AIF mRNA at different time-points.

Form:Solid

IC50& Target:HIV-1 reverse transcriptase

Specifications

Synonyms

DTXSID301319075 | Nigranoic acid | CHEBI:66626 | Q27135245 | HY-122935 | 3, 4-Secocycloarta-4(28), 24-(Z)-diene-3, 26-dioic acid | (2Z, 6R)-6-[(1R, 3aS, 3bS, 6S, 6aR, 7aS, 9aR)-6a-(2-carboxyethyl)-3a, 9a-dimethyl-6-(prop-1-en-2-yl)dodecahydro-1H-cyclopenta[a]cyclopr

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Nigranoic acid is a triterpenoid separated from Schisandra chinensis . Nigranoic acid inhibits HIV-1 reverse transcriptase . Nigranoic acid exhibits protective effects on brain through PARP/AIF signaling pathway in cerebral ischemia-reperfusion animal mod

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.

Action Type

INHIBITOR

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC(CCC=C(C)C(=O)O)C1CCC2(C1(CCC34C2CCC(C3(C4)CCC(=O)O)C(=C)C)C)C
• IUPAC Name: (Z,6R)-6-[(1S,4R,5R,8S,9S,12S,13R)-13-(2-carboxyethyl)-4,8-dimethyl-12-prop-1-en-2-yl-5-tetracyclo[7.5.0.01,13.04,8]tetradecanyl]-2-methylhept-2-enoic acid
• InChIKey: NJFOSFIPGRXARF-BRTULJEKSA-N
• INCHI: 1S/C30H46O4/c1-19(2)22-10-11-24-28(6)14-12-23(20(3)8-7-9-21(4)26(33)34)27(28,5)16-17-30(24)18-29(22,30)15-13-25(31)32/h9,20,22-24H,1,7-8,10-18H2,2-6H3,(H,31,32)(H,33,34)/b21-9-/t20-,22+,23-,24+,27-,28+,29-,30+/m1/s1
• Isomeric SMILES: C[C@H](CC/C=C(/C)\C(=O)O)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@H]([C@]3(C4)CCC(=O)O)C(=C)C)C)C
• Alternate CAS: 39111-07-4
• PubChem CID: 10814237
• MeSH Entry Terms: 3,4-secocycloarta-4(28),24(Z)-diene-3,26-dioic acid;nigranoic acid
• Molecular Weight: 470.68

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Triterpenoids
• Alternative Parents: Carbocyclic fatty acids Medium-chain fatty acids Methyl-branched fatty acids Unsaturated fatty acids Dicarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Triterpenoid - Carbocyclic fatty acid - Medium-chain fatty acid - Branched fatty acid - Methyl-branched fatty acid - Dicarboxylic acid or derivatives - Unsaturated fatty acid - Fatty acyl - Fatty acid - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Carbonyl group - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
• External Descriptors: dicarboxylic acid - tetracyclic triterpenoid

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(non-human)

pol Human immunodeficiency virus type 1 protease (9113 Activities)

Discover Target: pol

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

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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

Human immunodeficiency virus 1 (70413 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

• Molecular Weight: 470.700 g/mol
• XLogP3: 8.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 470.34 Da
• Monoisotopic Mass: 470.34 Da
• Topological Polar Surface Area: 74.600 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 903.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Feng Tianda, Liu Yunhui, Li Chao, Li Zhen.  (2014)  Protective Effects of Nigranoic Acid on Cerebral Ischemia–Reperfusion Injury and its Mechanism Involving Apoptotic Signaling Pathway.  CELL BIOCHEMISTRY AND BIOPHYSICS,  71  (1): (345-351).  [PMID:25168103] [10.1007/s12013-014-0204-1]