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DERIVATIVE OF AKLANONIC ACID METHYL ESTER (AAME)

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Overview

Structure
DrugBank ID
DB04624
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
DERIVATIVE OF AKLANONIC ACID METHYL ESTER (AAME)
DrugBank Accession Number
DB04624
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 414.4053
Monoisotopic: 414.13146768
Chemical Formula
C22H22O8
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAklanonic acid methyl ester cyclase AcmANot AvailableStreptomyces galilaeus
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Anthracenes
Sub Class
Anthraquinones
Direct Parent
Anthraquinones
Alternative Parents
Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Methyl esters / Secondary alcohols / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 9,10-anthraquinone / Alcohol / Anthraquinone / Aromatic alcohol / Aromatic homopolycyclic compound / Aryl ketone / Carbonyl group / Carboxylic acid derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SIHNJMGWRHPFAZ-XHDPSFHLSA-N
InChI
InChI=1S/C22H22O8/c1-3-11(23)9-15(25)17-10(8-16(26)30-2)7-13-19(21(17)28)22(29)18-12(20(13)27)5-4-6-14(18)24/h4-7,11,15,23-25,28H,3,8-9H2,1-2H3/t11-,15+/m0/s1
IUPAC Name
methyl 2-{3-[(1R,3S)-1,3-dihydroxypentyl]-4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl}acetate
SMILES
[H][C@](O)(CC)C[C@@]([H])(O)C1=C(O)C2=C(C=C1CC(=O)OC)C(=O)C1=CC=CC(O)=C1C2=O

References

General References
Not Available
PubChem Compound
42627264
PubChem Substance
46507428
ChemSpider
25057517
ZINC
ZINC000012504442
PDBe Ligand
AKV
PDB Entries
2f99

Clinical Trials

Clinical Trials
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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 Solubility0.159 mg/mLALOGPS
logP2.86ALOGPS
logP3Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.01Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area141.36 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity107.78 m3·mol-1Chemaxon
Polarizability42.57 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.906
Blood Brain Barrier-0.7375
Caco-2 permeable+0.5894
P-glycoprotein substrateSubstrate0.7208
P-glycoprotein inhibitor INon-inhibitor0.8921
P-glycoprotein inhibitor IINon-inhibitor0.8325
Renal organic cation transporterNon-inhibitor0.8981
CYP450 2C9 substrateNon-substrate0.7678
CYP450 2D6 substrateNon-substrate0.8753
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.6025
CYP450 2C9 inhibitorNon-inhibitor0.7973
CYP450 2D6 inhibitorNon-inhibitor0.7478
CYP450 2C19 inhibitorNon-inhibitor0.8078
CYP450 3A4 inhibitorNon-inhibitor0.6041
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7244
Ames testAMES toxic0.8192
CarcinogenicityNon-carcinogens0.9124
BiodegradationNot ready biodegradable0.9394
Rat acute toxicity3.1509 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.944
hERG inhibition (predictor II)Non-inhibitor0.8421
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00os-0009200000-748fd3433ca260cb197d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-0019100000-267423b125646cb3ef6c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05p9-9038200000-33d64e072836df76de48
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1019000000-814a74caa6ecd56b1e6c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00li-4079100000-9b84447a77461e4cfa84
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9066000000-be295d5d3a5ed036f0be
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.09236
predicted
DeepCCS 1.0 (2019)
[M+H]+192.48795
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.40047
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Aklanonic acid methyl ester cyclase AcmA
Kind
Protein
Organism
Streptomyces galilaeus
Pharmacological action
Unknown
General Function
Involved in the biosynthesis of aklavinone which is an important precursor common to the formation of the clinically significant anthracyclines such as carminomycin, daunorubicin (daunomycin), rhodomycin, aclacinomycin T (aklavin) and aclacinomycin A (aclarubicin). These compounds are aromatic polyketide antibiotics that exhibit high cytotoxicity and are widely applied in the chemotherapy of a variety of cancers. Catalyzes the cyclization of aklanonic acid methyl ester to yield aklaviketone. It is also able to use nogalonic acid methyl ester as substrate, but produces exclusively auraviketone with C9-R stereochemistry.
Specific Function
intramolecular lyase activity
Gene Name
acma
Uniprot ID
O52646
Uniprot Name
Aklanonic acid methyl ester cyclase AcmA
Molecular Weight
16730.765 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. [Article]

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52