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Aristolochic acid B

CAT: 0804-HY-N0511-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0511-01Size:1 mg
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Description
Aristolochic acid B (Aristolochic Acid II) is an orally active major component of aristolochic acid (AA). Aristolochic acid B can be isolated from plants of the genus Aristolochica. Aristolochic acid B forms DNA adducts. Aristolochic acid B is mutagenic. Aristolochic acid B exhibits a greater carcinogenic risk in vivo than Aristolochic acid I[2][3].
CAS Number
475-80-9
Product Name Alternative
Aristolochic acid II
UNSPSC
12352005
Hazard Statement
H301+H311+H331, H341, H351
Target
DNA Alkylator/Crosslinker
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/aristolochic-acid-b.html
Purity
99.92
Solubility
DMSO : 11.11 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C(C1=C2C([N+]([O-])=O)=CC3=CC=CC=C3C2=C(OCO4)C4=C1)O
Molecular Formula
C16H9NO6
Molecular Weight
311.25
Precautions
H301+H311+H331, H341, H351
References & Citations
[1]Xing G, et al. Comparison of the mutagenicity of aristolochic acid I and aristolochic acid II in the gpt delta transgenic mouse kidney. Mutat Res. 2012 Mar 18;743 (1-2) :52-8.|[2]Yeh YH, et al. Short-term toxicity of aristolochic acid, aristolochic acid-I and aristolochic acid-II in rats. Food Chem Toxicol. 2008 Mar;46 (3) :1157-63. |[3]Schmeiser HH, et al. DNA adduct formation of aristolochic acid I and II in vitro and in vivo. Carcinogenesis. 1988 Feb;9 (2) :297-303.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Aristolochic Acid Ii

Aristolochic acid B is an aristolochic acid that is phenanthrene-1-carboxylic acid substituted by a methylenedioxy group at the 3,4 positions and by a nitro group at position 10. It has a role as a metabolite, a mutagen, a carcinogenic agent and a nephrotoxin. It is a member of aristolochic acids, a monocarboxylic acid, an aromatic ether, a C-nitro compound, an organic heterotetracyclic compound and a cyclic acetal.

CAS Number475-80-9
PubChem CID108168
IUPAC Name6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
Molecular FormulaC16H9NO6
Molecular Weight311.24
XLogP3.6
Topological Polar Surface Area102
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Heavy Atom Count23
Formal Charge0
Complexity505
SMILES
C1OC2=C(O1)C3=C(C(=C2)C(=O)O)C(=CC4=CC=CC=C43)[N+](=O)[O-]
InChI
InChI=1S/C16H9NO6/c18-16(19)10-6-12-15(23-7-22-12)14-9-4-2-1-3-8(9)5-11(13(10)14)17(20)21/h1-6H,7H2,(H,18,19)
InChIKey
MEEXETVZNQYRSP-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Aristolochic Acid Ii
CAS: 475-80-9
CID: 108168
Formula: C16H9NO6
MW: 311.24
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight311.24
XLogP33.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Exact Mass311.04298701
Monoisotopic Mass311.04298701
Topological Polar Surface Area102 Ų
Heavy Atom Count23
Formal Charge0
Complexity505
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes