9-Hydroxy-8-Methoxy-6-Nitro-Phenanthrol[3,4-D][1,3]Dioxole-5-Carboxylic Acid

Identification

Name
9-Hydroxy-8-Methoxy-6-Nitro-Phenanthrol[3,4-D][1,3]Dioxole-5-Carboxylic Acid
Accession Number
DB02636  (EXPT00354)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 357.2711
Monoisotopic: 357.048466333
Chemical Formula
C17H11NO8
InChI Key
UCLGCTLOEZZSLA-UHFFFAOYSA-N
InChI
InChI=1S/C17H11NO8/c1-24-15-8-4-10(18(22)23)13-9(17(20)21)5-12-16(26-6-25-12)14(13)7(8)2-3-11(15)19/h2-5,19H,6H2,1H3,(H,20,21)
IUPAC Name
5-hydroxy-6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2(7),3,5,8,11,13(17)-heptaene-11-carboxylic acid
SMILES
COC1=C(O)C=CC2=C1C=C(C1=C2C2=C(OCO2)C=C1C(O)=O)[N+]([O-])=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGroup IIE secretory phospholipase A2Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
1941
PubChem Substance
46505836
ChemSpider
1865
BindingDB
50306859
ChEMBL
CHEMBL600828
PDBe Ligand
9AR
PDB Entries
1fv0 / 4yz7

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0747 mg/mLALOGPS
logP2.53ALOGPS
logP2.71ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area131.04 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.75 m3·mol-1ChemAxon
Polarizability33.24 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8357
Blood Brain Barrier-0.6685
Caco-2 permeable-0.5313
P-glycoprotein substrateNon-substrate0.63
P-glycoprotein inhibitor INon-inhibitor0.6464
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.8485
CYP450 2C9 substrateNon-substrate0.7466
CYP450 2D6 substrateNon-substrate0.8402
CYP450 3A4 substrateSubstrate0.6274
CYP450 1A2 substrateInhibitor0.7787
CYP450 2C9 inhibitorNon-inhibitor0.7711
CYP450 2D6 inhibitorNon-inhibitor0.9052
CYP450 2C19 inhibitorNon-inhibitor0.801
CYP450 3A4 inhibitorNon-inhibitor0.8396
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6013
Ames testAMES toxic0.8049
CarcinogenicityNon-carcinogens0.7363
BiodegradationNot ready biodegradable0.8877
Rat acute toxicity2.8841 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.916
hERG inhibition (predictor II)Non-inhibitor0.856
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Aristolochic acids and derivatives
Direct Parent
Aristolochic acids and derivatives
Alternative Parents
Phenanthrols / Naphthalenecarboxylic acids / Nitronaphthalenes / Naphthols and derivatives / Benzodioxoles / Nitroaromatic compounds / Anisoles / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Organic oxoazanium compounds
show 9 more
Substituents
Aristolochic acid or derivatives / Phenanthrol / 1-naphthalenecarboxylic acid / 1-naphthalenecarboxylic acid or derivatives / 1-nitronaphthalene / 2-nitronaphthalene / 2-naphthol / Naphthalene / Benzodioxole / Nitroaromatic compound
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase a2 activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name
PLA2G2E
Uniprot ID
Q9NZK7
Uniprot Name
Group IIE secretory phospholipase A2
Molecular Weight
15988.525 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on March 01, 2020 18:58

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