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(5S)-5-(2-amino-2-oxoethyl)-4-oxo-N-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)methyl]-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine-2-carboxamide

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Identification

Generic Name
(5S)-5-(2-amino-2-oxoethyl)-4-oxo-N-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)methyl]-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine-2-carboxamide
DrugBank Accession Number
DB07397
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 467.498
Monoisotopic: 467.126339497
Chemical Formula
C22H21N5O5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNeutrophil collagenaseNot 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

Adverse Effects
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Toxicity

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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxazines
Sub Class
Benzoxazinones
Direct Parent
Benzoxazinones
Alternative Parents
Benzomorpholines / Thienopyrimidines / Pyrimidinecarboxylic acids and derivatives / 2-heteroaryl carboxamides / Pyrimidones / Alkyl aryl ethers / Benzenoids / Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides
show 9 more
Substituents
2-heteroaryl carboxamide / Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzomorpholine / Benzoxazinone / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ITADELAVAWJACR-NSHDSACASA-N
InChI
InChI=1S/C22H21N5O5S/c23-15(28)7-11-2-1-3-14-17(11)18-20(30)26-19(27-22(18)33-14)21(31)24-8-10-4-5-13-12(6-10)25-16(29)9-32-13/h4-6,11H,1-3,7-9H2,(H2,23,28)(H,24,31)(H,25,29)(H,26,27,30)/t11-/m0/s1
IUPAC Name
(13S)-13-(carbamoylmethyl)-3-oxo-N-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)methyl]-8-thia-4,6-diazatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),5-triene-5-carboxamide
SMILES
[H][C@@]1(CC(N)=O)CCCC2=C1C1=C(S2)N=C(NC1=O)C(=O)NCC1=CC=C2OCC(=O)NC2=C1

References

General References
Not Available
PubChem Compound
25174099
PubChem Substance
99443868
ChemSpider
25060640
ZINC
ZINC000039153190
PDBe Ligand
AXA
PDB Entries
3dng

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 Solubility0.0202 mg/mLALOGPS
logP1.35ALOGPS
logP0.79Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.43Chemaxon
pKa (Strongest Basic)-0.98Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area151.98 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity121.61 m3·mol-1Chemaxon
Polarizability47.15 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7642
Blood Brain Barrier+0.6515
Caco-2 permeable-0.7296
P-glycoprotein substrateSubstrate0.7423
P-glycoprotein inhibitor INon-inhibitor0.9368
P-glycoprotein inhibitor IINon-inhibitor0.9898
Renal organic cation transporterNon-inhibitor0.7674
CYP450 2C9 substrateNon-substrate0.8728
CYP450 2D6 substrateNon-substrate0.7771
CYP450 3A4 substrateNon-substrate0.5559
CYP450 1A2 substrateNon-inhibitor0.584
CYP450 2C9 inhibitorInhibitor0.5852
CYP450 2D6 inhibitorNon-inhibitor0.8826
CYP450 2C19 inhibitorNon-inhibitor0.5707
CYP450 3A4 inhibitorInhibitor0.5182
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5131
Ames testNon AMES toxic0.5102
CarcinogenicityNon-carcinogens0.8897
BiodegradationNot ready biodegradable0.9869
Rat acute toxicity2.3107 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9753
hERG inhibition (predictor II)Inhibitor0.5365
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/MSsplash10-0udi-0000900000-9bdac950c828e0b25a6b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-066s-0000900000-72174130aab555c54bf2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0070900000-cfb613238786d80916d8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00r2-2041900000-4d0aae09cdb7ddd9fdf5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fr-0593400000-514e327e073732bd9f5d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6891500000-e18a8e1c94f3ea682abb
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]-199.23459
predicted
DeepCCS 1.0 (2019)
[M+H]+201.5926
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.6996
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Neutrophil collagenase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Can degrade fibrillar type I, II, and III collagens
Specific Function
endopeptidase activity
Gene Name
MMP8
Uniprot ID
P22894
Uniprot Name
Neutrophil collagenase
Molecular Weight
53411.72 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 15, 2010 21:21 / Updated at June 12, 2020 16:52