N-[[2-METHYL-4-HYDROXYCARBAMOYL]BUT-4-YL-N]-BENZYL-P-[PHENYL]-P-[METHYL]PHOSPHINAMID

Identification

Generic Name
N-[[2-METHYL-4-HYDROXYCARBAMOYL]BUT-4-YL-N]-BENZYL-P-[PHENYL]-P-[METHYL]PHOSPHINAMID
DrugBank Accession Number
DB08507
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 374.4137
Monoisotopic: 374.175929252
Chemical Formula
C20H27N2O3P
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UStromelysin-1Not 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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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
Leucine and derivatives
Alternative Parents
Benzene and substituted derivatives / Hydroxamic acids / Organopnictogen compounds / Organophosphorus compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Hydrocarbon derivative / Hydroxamic acid / Leucine or derivatives / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
KGUVBHLPMGERAT-NIYFSFCBSA-N
InChI
InChI=1S/C20H27N2O3P/c1-16(2)14-19(20(23)21-24)22(15-17-10-6-4-7-11-17)26(3,25)18-12-8-5-9-13-18/h4-13,16,19,24H,14-15H2,1-3H3,(H,21,23)/t19-,26-/m1/s1
IUPAC Name
(2R)-2-{benzyl[(R)-methyl(phenyl)phosphoryl]amino}-N-hydroxy-4-methylpentanamide
SMILES
[H][C@](CC(C)C)(N(CC1=CC=CC=C1)[P@](C)(=O)C1=CC=CC=C1)C(=O)NO

References

General References
Not Available
PubChem Compound
9543420
PubChem Substance
99444978
ChemSpider
7822389
BindingDB
50291979
ChEMBL
CHEMBL176602
ZINC
ZINC000001489206
PDBe Ligand
S27
PDB Entries
1b3d

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 Solubility0.00715 mg/mLALOGPS
logP2.35ALOGPS
logP3.04Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.72Chemaxon
pKa (Strongest Basic)1.94Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area69.64 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity104.41 m3·mol-1Chemaxon
Polarizability38.83 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7314
Blood Brain Barrier+0.6698
Caco-2 permeable-0.5651
P-glycoprotein substrateSubstrate0.6993
P-glycoprotein inhibitor INon-inhibitor0.6639
P-glycoprotein inhibitor IINon-inhibitor0.6957
Renal organic cation transporterNon-inhibitor0.8853
CYP450 2C9 substrateNon-substrate0.6596
CYP450 2D6 substrateNon-substrate0.7936
CYP450 3A4 substrateSubstrate0.5576
CYP450 1A2 substrateNon-inhibitor0.8417
CYP450 2C9 inhibitorNon-inhibitor0.7588
CYP450 2D6 inhibitorNon-inhibitor0.8378
CYP450 2C19 inhibitorNon-inhibitor0.6809
CYP450 3A4 inhibitorInhibitor0.6135
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9263
Ames testNon AMES toxic0.564
CarcinogenicityNon-carcinogens0.5776
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5626 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9962
hERG inhibition (predictor II)Non-inhibitor0.6831
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/MSsplash10-004i-0439000000-5d7f5ca54520dd17187d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0109000000-4eb19fb097170b42292b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0923000000-1692723bd0fd9235f0bd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9767000000-f92875611d7643359e27
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0596-7951000000-496357453665d05cc15f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-2930000000-5e49677067e0524db496
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]-183.33543
predicted
DeepCCS 1.0 (2019)
[M+H]+185.69344
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.38304
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Stromelysin-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
Gene Name
MMP3
Uniprot ID
P08254
Uniprot Name
Stromelysin-1
Molecular Weight
53976.84 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