NAV

[(3S)-9-hydroxy-1-methyl-10-oxo-4,10-dihydro-3H-benzo[g]isochromen-3-yl]acetic acid

Identification

Generic Name
[(3S)-9-hydroxy-1-methyl-10-oxo-4,10-dihydro-3H-benzo[g]isochromen-3-yl]acetic acid
DrugBank Accession Number
DB08541
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 286.2794
Monoisotopic: 286.084123558
Chemical Formula
C16H14O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UActII proteinNot AvailableStreptomyces coelicolor
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 naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Naphthopyrans
Sub Class
Naphthopyranones
Direct Parent
Naphthopyranones
Alternative Parents
Naphthalenes / Aryl ketones / Pyranones and derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous esters / Vinylogous acids / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids
show 2 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic heteropolycyclic compound / Aryl ketone / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Ketone
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cyclic ketone, monocarboxylic acid, phenols, polyketide, aromatic ketone, naphthopyran (CHEBI:31034)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HHXSOTFPYPQSBU-NSHDSACASA-N
InChI
InChI=1S/C16H14O5/c1-8-14-10(6-11(21-8)7-13(18)19)5-9-3-2-4-12(17)15(9)16(14)20/h2-5,11,17H,6-7H2,1H3,(H,18,19)/t11-/m0/s1
IUPAC Name
2-[(3S)-9-hydroxy-1-methyl-10-oxo-3H,4H,10H-naphtho[2,3-c]pyran-3-yl]acetic acid
SMILES
[H][C@@]1(CC(O)=O)CC2=CC3=C(C(O)=CC=C3)C(=O)C2=C(C)O1

References

General References
Not Available
KEGG Compound
C12434
PubChem Compound
443833
PubChem Substance
99445012
ChemSpider
25058731
ChEBI
31034
ZINC
ZINC000024960091
PDBe Ligand
SDN
PDB Entries
3b6c / 6vw4

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 Solubility0.13 mg/mLALOGPS
logP2.01ALOGPS
logP1.94Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.73Chemaxon
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area83.83 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity77.35 m3·mol-1Chemaxon
Polarizability29.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8431
Blood Brain Barrier+0.7219
Caco-2 permeable+0.6655
P-glycoprotein substrateSubstrate0.7547
P-glycoprotein inhibitor INon-inhibitor0.8793
P-glycoprotein inhibitor IINon-inhibitor0.8898
Renal organic cation transporterNon-inhibitor0.8696
CYP450 2C9 substrateNon-substrate0.7661
CYP450 2D6 substrateNon-substrate0.8334
CYP450 3A4 substrateNon-substrate0.5054
CYP450 1A2 substrateNon-inhibitor0.7005
CYP450 2C9 inhibitorInhibitor0.7546
CYP450 2D6 inhibitorNon-inhibitor0.7884
CYP450 2C19 inhibitorNon-inhibitor0.7369
CYP450 3A4 inhibitorNon-inhibitor0.6057
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.553
Ames testNon AMES toxic0.6476
CarcinogenicityNon-carcinogens0.9536
BiodegradationNot ready biodegradable0.704
Rat acute toxicity3.5183 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8579
hERG inhibition (predictor II)Non-inhibitor0.8679
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-MSsplash10-000w-3790000000-5617d5cf6ac0666be3f0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-fdd6304a04c7b4fcd317
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00du-0090000000-41eafedc259cdbb81075
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-424f397484861a79aba9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pvr-0190000000-a3b98e95a8b7c0edd9d7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-9840000000-f4d780031543e954bda7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-066s-0390000000-d21b1014a7bf1c17841e
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]-178.8934432
predicted
DarkChem Lite v0.1.0
[M-H]-161.83647
predicted
DeepCCS 1.0 (2019)
[M+H]+177.4274432
predicted
DarkChem Lite v0.1.0
[M+H]+164.21632
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.5064432
predicted
DarkChem Lite v0.1.0
[M+Na]+170.89024
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. ActII protein
Kind
Protein
Organism
Streptomyces coelicolor
Pharmacological action
Unknown
General Function
Dna binding
Specific Function
Not Available
Gene Name
actII
Uniprot ID
Q53901
Uniprot Name
ActII protein
Molecular Weight
28267.92 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 21:32 / Updated at June 12, 2020 16:52