L-Histidine Beta Naphthylamide

Identification

Generic Name
L-Histidine Beta Naphthylamide
DrugBank Accession Number
DB01938
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 280.3244
Monoisotopic: 280.132411154
Chemical Formula
C16H16N4O
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHut operon positive regulatory proteinNot AvailableBacillus subtilis (strain 168)
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 histidine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Histidine and derivatives
Alternative Parents
Alpha amino acid amides / Naphthalenes / N-arylamides / Aralkylamines / Fatty amides / Imidazoles / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Alpha-amino acid amide / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonyl group / Carboxamide group / Fatty acyl
show 17 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
DKDILZBBFKZMRO-OAHLLOKOSA-N
InChI
InChI=1S/C16H16N4O/c17-15(8-14-9-18-10-19-14)16(21)20-13-6-5-11-3-1-2-4-12(11)7-13/h1-7,9-10,15H,8,17H2,(H,18,19)(H,20,21)/t15-/m1/s1
IUPAC Name
(2R)-2-amino-3-(1H-imidazol-5-yl)-N-(naphthalen-2-yl)propanamide
SMILES
[H][C@@](N)(CC1=CN=CN1)C(=O)NC1=CC=C2C=CC=CC2=C1

References

General References
Not Available
PubChem Compound
6541406
PubChem Substance
46505793
ChemSpider
16744024
ZINC
ZINC000008585585
PDBe Ligand
HBN
PDB Entries
1vea

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 Solubility0.104 mg/mLALOGPS
logP1.1ALOGPS
logP1.07Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.75Chemaxon
pKa (Strongest Basic)8.01Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area83.8 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity82.79 m3·mol-1Chemaxon
Polarizability30.46 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9763
Blood Brain Barrier+0.9587
Caco-2 permeable-0.6575
P-glycoprotein substrateNon-substrate0.5214
P-glycoprotein inhibitor INon-inhibitor0.8638
P-glycoprotein inhibitor IINon-inhibitor0.8905
Renal organic cation transporterNon-inhibitor0.8497
CYP450 2C9 substrateNon-substrate0.8424
CYP450 2D6 substrateNon-substrate0.8121
CYP450 3A4 substrateNon-substrate0.6237
CYP450 1A2 substrateInhibitor0.7963
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorInhibitor0.6143
CYP450 2C19 inhibitorInhibitor0.5992
CYP450 3A4 inhibitorInhibitor0.808
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9037
Ames testNon AMES toxic0.6977
CarcinogenicityNon-carcinogens0.8941
BiodegradationNot ready biodegradable0.9858
Rat acute toxicity2.2736 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9887
hERG inhibition (predictor II)Non-inhibitor0.6483
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-MSsplash10-001i-9720000000-52fde5563c884079fa18
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0590000000-b65913463ae031f80aa1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004u-2590000000-ffda25f8b1dafe4c5a9e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0090000000-4d2d6ee60a48f39575a2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-4920000000-b125e5ff146778cf5bc7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-9000000000-eaae29a6b91f4f1d361a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-dc4c507e9530ae3bf4a5
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]-158.72673
predicted
DeepCCS 1.0 (2019)
[M+H]+161.08473
predicted
DeepCCS 1.0 (2019)
[M+Na]+167.74187
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Mrna binding
Specific Function
Antiterminator that binds to cis-acting regulatory sequences on the mRNA in the presence of histidine, thereby suppressing transcription termination and activating the hut operon for histidine util...
Gene Name
hutP
Uniprot ID
P10943
Uniprot Name
Hut operon positive regulatory protein
Molecular Weight
16195.415 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