6(5H)-Phenanthridinone

HCID 1853CAS 1015-89-0
Substructure searchFind similar structures

Basic information

Standard SMILES
O=c1[nH]c2ccccc2c2ccccc12
InChIKey
RZFVLEJOHSLEFR-UHFFFAOYSA-N
Molecular formula
C13H9NO
Average molar mass
195.22 g/mol
Monoisotopic mass
195.06841391

Names & identifiers

Preferred name
6(5H)-Phenanthridinone
IUPAC
5H-phenanthridin-6-one
English name
6(5H)-Phenanthridone
Molecular formula
C13H9NO
Molecular weight
195.22

Names & synonyms

6(5H)-Phenanthridinone1015-89-0Phenanthridin-6(5H)-onePhenanthridone6-Phenanthridinol6-Phenanthridinone6-PhenanthridonePhenantridoneAVQ13AUB5JNSC-11021NSC-40943NSC-61083
Show more names
PHENANTHRIDINONE6(5H)-PhenantridinonePJ 97ANSC 11021NSC 40943NSC 61083WD 99-004344
DTXSID0074423CHEBI:75292RefChem:860541DTXCID1032640213-804-35H-phenanthridin-6-one6-(5H)-phenanthridinonephenanthridin-6-ol

Database identifiers

CAS
1015-89-0
PubChem CID
1853
DTXSID
DTXSID0074423
ChEMBL
CHEMBL45245
ChEBI
CHEBI:75292
UNII
AVQ13AUB5J
EC Number
213-804-3
Nikkaji
J69.574B

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
29.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
15

Experimental & physicochemical properties

Physical DescriptionPowder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
290 · 290-292 °C(lit.)
Boiling point
435 °C · 435 °C
Density
1.23 · 1.230±0.06 g/cm3(Predicted)
storage temp.
Sealed in dry,Room Temperature
solubility
1 mg/mL; · DMF: 1mg/mL; DMF:PBS (pH 7.2) (1:5): 0.16mg/mL
pka
13.27 · 13.27±0.20(Predicted)

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
SG0370000
hs_code
29337900
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationChemicals and drugs that inhibit the action of POLY(ADP-RIBOSE)POLYMERASES.

Uses & manufacturing

UsesA coal tar derivative; [ChemIDplus]
Applications · 3 items

Uses6-Phenanthridone is a poly(ADP-ribose) polymerase (PARP) inhibitor with immunosuppressive effects. 6-Phenanthridone has been shown to inhibit concanavalin A-induced lymphocyte proliferation.

Uses6(5H)-Phenanthridinone is used as a probe into the role of PARP in cellular response to irradiation. Treatment of cells with 6(5H)-Phenanthridinone and various DNA-damaging agents showed a resistance to apoptosis. It acts as a reactant in the synthesis of 5,6-dihydrophenanthridine sulfonamides, oxidative coupling with diphenylacetylene, direct copper acetate-catalyzed N-cyclopropylation of cyclic amides. It is used as HIV-1 integrase inhibitor.

General Description6-(5H)-Phenanthridinone is an inhibitor of poly(ADP-ribose)polymerase (PARP)-1 activity. The ability of 6-(5H)-phenanthridinone to potentiate the effect of ionizing radiation on tumour cells was evaluated. Action of 6-(5H)-phenanthridinone, one of the most potent PARP inhibitor, on RDM4 murine lymphoma cells in culture was evaluated.

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）400-6005915 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
常熟市海天医药原料有限公司13913622609

Additional notes

DefinitionChEBI: A member of the class of phenanthridines that is phenanthridine with an oxo substituent at position 6. A poly(ADP-ribose) polymerase (PARP) inhibitor, it has been shown to exhibit immunosuppressive activity.

Related reactions

15 records
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Linked notes

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