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475-80-9 molecular structure
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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

ChemBase ID: 160804
Molecular Formular: C16H9NO6
Molecular Mass: 311.24576
Monoisotopic Mass: 311.04298701
SMILES and InChIs

SMILES:
c1cccc2c1c1c(c(c2)[N+](=O)[O-])c(cc2c1OCO2)C(=O)O
Canonical SMILES:
[O-][N+](=O)c1cc2ccccc2c2c1c(cc1c2OCO1)C(=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

Cite this record

CBID:160804 http://www.chembase.cn/molecule-160804.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional name
aristolochic acid II
Synonyms
6-Nitro-phenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid
Aristolochic Acid II
3,4-(Methylenedioxy)-10-nitrophenanthrene-1-carboxylic Acid
Aristolochic Acid B
CAS Number
475-80-9
PubChem SID
162254939
PubChem CID
108168

DATA SOURCES

DATA SOURCES

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Data Source Data ID
TRC A771305 external link Add to cart
PubChem 108168 external link
Data Source Data ID Price
TRC
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Data Source Data ID
PubChem 108168 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.324431  H Acceptors
H Donor LogD (pH = 5.5) 1.0133542 
LogD (pH = 7.4) -0.24781078  Log P 3.1729999 
Molar Refractivity 79.3062 cm3 Polarizability 32.00752 Å3
Polar Surface Area 101.58 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - A771305 external link
Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Coutts, et al.: J. Pharm. Pharmacol., 11, 607 (1959)
  • • Kupchan, D., et al.: J. Med. Pharm. Chem., 5, 657 (1959)
  • • Mix, D.B., et al.: J. Nat. Prod., 45, 657 (1959)
  • • Mengs, U., et al.: Arch. Toxixol., 59, 328 (1959)
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PATENTS

PATENTS

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INTERNET

INTERNET

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