ChemFOnt: Showing chemical card for Aristolochic acid B (CFc000228134)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:53:46 UTC

Chemfont ID

CFc000228134

Molecule Identification

Common Name

Aristolochic acid B

Definition

Aristolochic acid B, also known as aristolochate b, 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. Based on a literature review a significant number of articles have been published on Aristolochic acid B.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Aristolochate b	Generator
Aristolochate II	Generator
Aristolochic acid b	MeSH
6-Nitrophenanthro(3,4-D)-3-dioxole-5-carboxylic acid	MeSH
9-Nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2,4,6,8,11,13(17)-heptaene-11-carboxylate	Generator
9-Nitro-14,16-dioxatetracyclo[8.7.0.0,.0,]heptadeca-1(10),2,4,6,8,11,13(17)-heptaene-11-carboxylate	Generator

Chemical Formula

C₁₆H₉NO₆

Average Molecular Weight

311.249

Monoisotopic Molecular Weight

311.042987014

IUPAC Name

9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid

Traditional Name

aristolochic acid II

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O

InChI Identifier

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)

InChI Key

MEEXETVZNQYRSP-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Aristolochic acids and derivatives

Direct Parent

Aristolochic acids and derivatives

Alternative Parents

Substituents

Aristolochic acid or derivatives
1-naphthalenecarboxylic acid
1-naphthalenecarboxylic acid or derivatives
1-nitronaphthalene
2-nitronaphthalene
Naphthalene
Benzodioxole
Nitroaromatic compound
C-nitro compound
Organic nitro compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Organic oxoazanium
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.68	ALOGPS
logP	3.17	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	98.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.3 m³·mol⁻¹	ChemAxon
Polarizability	29.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00021671

Chemspider ID

97250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aristolochic acid

METLIN ID

Not Available

PubChem Compound

108168

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Aristolochic acid B (CFc000228134)

MOL for CFc000228134 (Aristolochic acid B)

3D MOL for CFc000228134 (Aristolochic acid B)

3D SDF for CFc000228134 (Aristolochic acid B)

3D-SDF for CFc000228134 (Aristolochic acid B)

PDB for CFc000228134 (Aristolochic acid B)

3D PDB for CFc000228134 (Aristolochic acid B)

SMILES for CFc000228134 (Aristolochic acid B)

INCHI for CFc000228134 (Aristolochic acid B)

Structure for CFc000228134 (Aristolochic acid B)

3D Structure for CFc000228134 (Aristolochic acid B)