NAV

(3S)-3-hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione

Identification

Generic Name
(3S)-3-hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione
DrugBank Accession Number
DB07339
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 179.1727
Monoisotopic: 179.058243159
Chemical Formula
C9H9NO3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
URibosyldihydronicotinamide dehydrogenase [quinone]Not 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 indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Not Available
Direct Parent
Indoles and derivatives
Alternative Parents
N-alkylpyrrolidines / Vinylogous amides / Trialkylamines / Secondary alcohols / Cyclic ketones / Enamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Amine / Azacycle / Carbonyl group / Cyclic ketone / Enamine / Hydrocarbon derivative / Indole or derivatives / Ketone
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
RPHLQSHHTJORHI-SECBINFHSA-N
InChI
InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3/t9-/m1/s1
IUPAC Name
(3S)-3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione
SMILES
[H][C@@]1(O)CN(C)C2=CC(=O)C(=O)C=C12

References

General References
Not Available
PubChem Compound
23270857
PubChem Substance
99443810
ChemSpider
10430889
ZINC
ZINC000001600115
PDBe Ligand
AD1
PDB Entries
2qmy

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 Solubility68.0 mg/mLALOGPS
logP0.08ALOGPS
logP-0.31Chemaxon
logS-0.42ALOGPS
pKa (Strongest Acidic)14.09Chemaxon
pKa (Strongest Basic)-2.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area57.61 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity48.56 m3·mol-1Chemaxon
Polarizability17.39 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7843
Caco-2 permeable+0.5644
P-glycoprotein substrateSubstrate0.5988
P-glycoprotein inhibitor IInhibitor0.5313
P-glycoprotein inhibitor IINon-inhibitor0.9268
Renal organic cation transporterNon-inhibitor0.7982
CYP450 2C9 substrateNon-substrate0.7914
CYP450 2D6 substrateNon-substrate0.8005
CYP450 3A4 substrateSubstrate0.5742
CYP450 1A2 substrateNon-inhibitor0.5692
CYP450 2C9 inhibitorNon-inhibitor0.8416
CYP450 2D6 inhibitorNon-inhibitor0.8619
CYP450 2C19 inhibitorNon-inhibitor0.7749
CYP450 3A4 inhibitorNon-inhibitor0.9783
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9424
Ames testNon AMES toxic0.5302
CarcinogenicityNon-carcinogens0.9517
BiodegradationNot ready biodegradable0.5333
Rat acute toxicity2.5920 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8552
hERG inhibition (predictor II)Non-inhibitor0.9476
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-MSsplash10-03di-3900000000-8d82eb154236f41ea5ba
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-e39c691350cfb1b01b99
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-1b1161f28f9bef1fef7c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qi-0900000000-29b62b4fc3747160b137
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01p9-0900000000-120d59a9fb8a271bb71e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-1900000000-eb444a46ae5c841a2735
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-0900000000-c4e414a987e6ecf13ed0
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]-141.78069
predicted
DeepCCS 1.0 (2019)
[M+H]+144.17624
predicted
DeepCCS 1.0 (2019)
[M+Na]+150.08876
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Ribosyldihydronicotinamide dehydrogenase [quinone]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadph dehydrogenase (quinone) activity
Specific Function
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vi...
Gene Name
NQO2
Uniprot ID
P16083
Uniprot Name
Ribosyldihydronicotinamide dehydrogenase [quinone]
Molecular Weight
25918.4 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 21:20 / Updated at June 12, 2020 16:52