NAV

N-[(5S,7R,8S,9S,10R)-8,9,10-Trihydroxy-7-(hydroxymethyl)-2,4-dioxo-6-oxa-1,3-diazaspiro[4.5]dec-3-yl]acetamide

Identification

Generic Name
N-[(5S,7R,8S,9S,10R)-8,9,10-Trihydroxy-7-(hydroxymethyl)-2,4-dioxo-6-oxa-1,3-diazaspiro[4.5]dec-3-yl]acetamide
DrugBank Accession Number
DB03835
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 305.2414
Monoisotopic: 305.085914471
Chemical Formula
C10H15N3O8
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, muscle formNot 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 c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
C-glycosyl compounds
Alternative Parents
Hydantoins / Alpha amino acids and derivatives / Diacylhydrazines / Monosaccharides / Oxanes / Semicarbazides / Dicarboximides / Acetamides / Organic carbonic acids and derivatives / Secondary alcohols
show 8 more
Substituents
Acetamide / Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Azacycle / C-glycosyl compound / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Carboxylic acid hydrazide
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MAHIOGAAEAWGLR-UTAYWCBXSA-N
InChI
InChI=1S/C10H15N3O8/c1-3(15)12-13-8(19)10(11-9(13)20)7(18)6(17)5(16)4(2-14)21-10/h4-7,14,16-18H,2H2,1H3,(H,11,20)(H,12,15)/t4-,5-,6+,7-,10+/m1/s1
IUPAC Name
N-[(5S,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-2,4-dioxo-6-oxa-1,3-diazaspiro[4.5]decan-3-yl]acetamide
SMILES
CC(=O)NN1C(=O)N[C@@]2(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C1=O

References

General References
Not Available
PubChem Compound
5288395
PubChem Substance
46506964
ChemSpider
4450585
ChEMBL
CHEMBL593335
ZINC
ZINC000003833806
PDBe Ligand
GL9
PDB Entries
1fu4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility99.8 mg/mLALOGPS
logP-2ALOGPS
logP-3.9Chemaxon
logS-0.49ALOGPS
pKa (Strongest Acidic)9.17Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area168.66 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity61.83 m3·mol-1Chemaxon
Polarizability26.75 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5418
Blood Brain Barrier-0.5971
Caco-2 permeable-0.7509
P-glycoprotein substrateNon-substrate0.647
P-glycoprotein inhibitor INon-inhibitor0.8473
P-glycoprotein inhibitor IINon-inhibitor0.9943
Renal organic cation transporterNon-inhibitor0.9585
CYP450 2C9 substrateNon-substrate0.733
CYP450 2D6 substrateNon-substrate0.8542
CYP450 3A4 substrateNon-substrate0.536
CYP450 1A2 substrateNon-inhibitor0.9208
CYP450 2C9 inhibitorNon-inhibitor0.9404
CYP450 2D6 inhibitorNon-inhibitor0.9422
CYP450 2C19 inhibitorNon-inhibitor0.922
CYP450 3A4 inhibitorNon-inhibitor0.9842
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9939
Ames testNon AMES toxic0.5496
CarcinogenicityNon-carcinogens0.9104
BiodegradationReady biodegradable0.5371
Rat acute toxicity2.0733 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9408
hERG inhibition (predictor II)Non-inhibitor0.9101
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-MSsplash10-0kg9-9330000000-8c8d342216bde6d9b6af
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0029000000-fa5f94df5a0f02a647e2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0129000000-274329d0d328b49c3a5e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0593000000-30b8b85f30093087ef2e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-0590000000-ce9d5921ff2c626cfb37
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pbi-1910000000-75d1ec344fdf07dcf9f4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f96-6790000000-d341ac2737bdc3f9e2ce
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]-162.18861
predicted
DeepCCS 1.0 (2019)
[M+H]+164.56004
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.54515
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glycogen phosphorylase, muscle form
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52