Aristolochic Acid is an alkaloid that was originally derived from Aristolochia radix. This compound is a potent PLA2 enzyme inhibitor and also suppresses edema-inducing activity as well as direct and indirect hemolytic activity. Specifically, Aristolochic Acid displays anti-inflammatory activity against edema in mouse foot pads induced by PLA2. Other experiments have shown this agent to be associated with aristolochic acid nephropathy. Mechanistic studies have reported Aristolochic Acid to play a regulatory role towards genes in DNA repair processes and responses to DNA damage stimulus, regulation of cell cycle, and apoptosis. More detailed studies have shown this compound to up-regulate GADD 45β, NAIP genes and down-regulate TP53, PARP1, ERCC1, OGG1/2, MGMT, and ERCC2 genes. Furthermore, a down-regulation of gene expression in anti-oxidant enzymes was also observed by Aristolochic Acid treatment of human kidney tubular cells. These studies suggest that oxidative stress plays a role in the cytotoxicity of Aristolochic Acid.
Aristolochic acid A is a potent phospholipase A2 inhibitor. Aristolochic acid A induces tumor formation in rat kidneys and apoptosis in human renal proximal tubular epithelial cells.

Specifications

Sinónimos

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Potent phospholipase A2 inhibitor, including calcium ionophore-induced phospholipase A2 activity in neutrophils. Kidney tumor initiator in experimental animal model.

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

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Grado

Moligand™

Tipo de acción

AGONIST

Mecanismo de acción

Agonist of TAS2R14;Agonist of TAS2R31;Agonist of TAS2R43

Pureza

≥98%

Nombres e identificadores

Pubchem Sid	504750543
Pubchem Sid Url	https://pubchem.ncbi.nlm.nih.gov/substance/504750543
Sonrisas canónicas	COC1=CC=CC2=C3C(=C(C=C21)[N+](=O)[O-])C(=CC4=C3OCO4)C(=O)O
IUPAC Name	8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
InChIKey	BBFQZRXNYIEMAW-UHFFFAOYSA-N
INCHI	1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)
Isómeros SMILES	COC1=CC=CC2=C3C(=C(C=C21)[N+](=O)[O-])C(=CC4=C3OCO4)C(=O)O
WGK Alemania	3
RTECS	CF3325000
CAS alternativo	313-67-7
Número NSC	11926
Términos de entrada MeSH	8-methoxy-6-nitrophenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid;aristolochic acid;aristolochic acid A;aristolochic acid I;aristolochic acid I, sodium salt;sodium aristolochate;Tardolyt
Peso molecular	341.27
Reaxy-Rn	345159
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=345159&ln=

Documentation

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Benzenoids
  - Clase Phenanthrenes and derivatives
    - Subclass Aristolochic acids and derivatives

Kingdom	Organic compounds
Superclass	Benzenoids
Clase	Phenanthrenes and derivatives
Subclass	Aristolochic acids and derivatives
Intermediate Tree Nodes	Not available
Direct Parent	Aristolochic acids and derivatives
Alternative Parents	Naphthalenecarboxylic acids Nitronaphthalenes Benzodioxoles Anisoles Nitroaromatic compounds Alkyl aryl ethers Acetals Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Carboxylic acids Organic oxoazanium compounds Monocarboxylic acids and derivatives Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic oxides
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Aristolochic acid or derivatives - 1-naphthalenecarboxylic acid - 1-naphthalenecarboxylic acid or derivatives - 1-nitronaphthalene - 2-nitronaphthalene - Naphthalene - Benzodioxole - Nitroaromatic compound - Anisole - Alkyl aryl ether - Organic nitro compound - C-nitro compound - Acetal - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
Descripción	This compound belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively.
External Descriptors	Isoquinoline alkaloids
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

Estructura 3D

Objetivos asociados (humanos)

TAS2R43 Tchem Taste receptor type 2 member 43 (0 Activities)

Discover Target: TAS2R43

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

TAS2R14 Tchem Taste receptor type 2 member 14 (0 Activities)

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

TAS2R31 Tchem Taste receptor type 2 member 31 (0 Activities)

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

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

PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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

PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

Discover Target: PIN1

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

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

A498 (42825 Activities)

Lot Number	Certificate Type	Fecha	Articulo
F2228059	Certificate of Analysis	Jan 19, 2026	A111318
E2015060	Certificate of Analysis	Sep 16, 2025	A111318
F2228055	Certificate of Analysis	Apr 02, 2024	A111318
K2124401	Certificate of Analysis	Aug 18, 2023	A111318
K2124426	Certificate of Analysis	Aug 18, 2023	A111318
B2325250	Certificate of Analysis	Nov 27, 2021	A111318

Solubilidad	Soluble in ethanol, acetone, chloroform, ether, aniline, alkalies, acetic acid, and DMSO (25 mg/ml), slightly soluble in water.practically Insoluble in benzene, and carbon disulfide.
Punto de fusión (°C)	278℃
Peso molecular	341.270 g/mol
XLogP3	3.600
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	341.054 Da
Monoisotopic Mass	341.054 Da
Topological Polar Surface Area	111.000 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	550.000
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

Aristolochic acid A - Moligand™, ≥98% , Agonist of TAS2R14;Agonist of TAS2R31;Agonist of TAS2R43, CAS No.313-67-7, Agonist of TAS2R14;Agonist of TAS2R31;Agonist of TAS2R43

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