NAV

TRW3-(2-AMINO-3-HYDROXY-PROPYL)-6-(N'-CYCLOHEXYL-HYDRAZINO)OCTAHYDRO-INDOL-7-OL

Identification

Generic Name
TRW3-(2-AMINO-3-HYDROXY-PROPYL)-6-(N'-CYCLOHEXYL-HYDRAZINO)OCTAHYDRO-INDOL-7-OL
DrugBank Accession Number
DB08646
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 310.3504
Monoisotopic: 310.14297584
Chemical Formula
C17H18N4O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAmicyaninNot AvailableParacoccus denitrificans
UMethylamine dehydrogenase heavy chainNot AvailableParacoccus denitrificans
UMethylamine dehydrogenase light chainNot AvailableParacoccus denitrificans
UCytochrome c-LNot AvailableParacoccus denitrificans
UQuinohemoprotein amine dehydrogenase subunit gammaNot AvailableParacoccus denitrificans
UQuinohemoprotein amine dehydrogenase 60 kDa subunitNot AvailableParacoccus denitrificans
UQuinohemoprotein amine dehydrogenase 40 kDa subunitNot AvailableParacoccus denitrificans
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 hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Hydroxyindoles
Direct Parent
Hydroxyindoles
Alternative Parents
3-alkylindoles / Phenylhydrazines / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / Substituted pyrroles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 3 more
Substituents
1-hydroxy-4-unsubstituted benzenoid / 3-alkylindole / Aldehyde / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Heteroaromatic compound
show 16 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
PSUOZWHAKZSNOB-LBPRGKRZSA-N
InChI
InChI=1S/C17H18N4O2/c18-12(10-22)8-11-9-19-16-14(11)6-7-15(17(16)23)21-20-13-4-2-1-3-5-13/h1-7,9-10,12,19-21,23H,8,18H2/t12-/m0/s1
IUPAC Name
(2S)-2-amino-3-[7-hydroxy-6-(2-phenylhydrazin-1-yl)-1H-indol-3-yl]propanal
SMILES
[H][C@](N)(CC1=CNC2=C1C=CC(NNC1=CC=CC=C1)=C2O)C=O

References

General References
Not Available
PubChem Compound
46937169
PubChem Substance
99445117
ChemSpider
25058064
ZINC
ZINC000100036939
PDBe Ligand
TRW
PDB Entries
1mg3 / 1pby

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 Solubility0.108 mg/mLALOGPS
logP2.5ALOGPS
logP2.34Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.4Chemaxon
pKa (Strongest Basic)7.64Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area103.17 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity92.16 m3·mol-1Chemaxon
Polarizability33.85 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.8941
Caco-2 permeable-0.5916
P-glycoprotein substrateNon-substrate0.6192
P-glycoprotein inhibitor INon-inhibitor0.9343
P-glycoprotein inhibitor IINon-inhibitor0.8442
Renal organic cation transporterNon-inhibitor0.8394
CYP450 2C9 substrateNon-substrate0.7829
CYP450 2D6 substrateNon-substrate0.7941
CYP450 3A4 substrateNon-substrate0.5827
CYP450 1A2 substrateInhibitor0.6991
CYP450 2C9 inhibitorNon-inhibitor0.6003
CYP450 2D6 inhibitorNon-inhibitor0.5792
CYP450 2C19 inhibitorInhibitor0.5796
CYP450 3A4 inhibitorInhibitor0.5802
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8355
Ames testAMES toxic0.6341
CarcinogenicityNon-carcinogens0.8287
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity2.5067 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.889
hERG inhibition (predictor II)Non-inhibitor0.6178
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/MSsplash10-03di-0397000000-32dc7d5bfc22b37bf350
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1029000000-2dd2db23f973d3088273
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-0590000000-1094b9be1b4787dbc83c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0671-4962000000-1dc48118b4826e03f5f3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xu-3981000000-bb6cad281472f381c125
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-2910000000-b26cea1c4319cbc9281b
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]-164.09773
predicted
DeepCCS 1.0 (2019)
[M+H]+166.45573
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.34422
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Amicyanin
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Electron carrier activity
Specific Function
Primary acceptor of electrons from methylamine dehydrogenase. Passes those electrons on either a soluble cytochrome c or to pseudoazurin.
Gene Name
mauC
Uniprot ID
P22364
Uniprot Name
Amicyanin
Molecular Weight
13983.11 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]
Details2. Methylamine dehydrogenase heavy chain
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Methylamine dehydrogenase (amicyanin) activity
Specific Function
Methylamine dehydrogenase carries out the oxidation of methylamine. Electrons are passed from methylamine dehydrogenase to amicyanin.
Gene Name
mauB
Uniprot ID
P29894
Uniprot Name
Methylamine dehydrogenase heavy chain
Molecular Weight
45439.73 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]
Details3. Methylamine dehydrogenase light chain
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Methylamine dehydrogenase (amicyanin) activity
Specific Function
Methylamine dehydrogenase carries out the oxidation of methylamine. Electrons are passed from methylamine dehydrogenase to amicyanin.
Gene Name
mauA
Uniprot ID
P22619
Uniprot Name
Methylamine dehydrogenase light chain
Molecular Weight
20392.855 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]
Details4. Cytochrome c-L
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Electron acceptor for MDH. Acts in methanol oxidation.
Gene Name
moxG
Uniprot ID
P29899
Uniprot Name
Cytochrome c-L
Molecular Weight
19395.54 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]
Details5. Quinohemoprotein amine dehydrogenase subunit gamma
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-nh2 group of donors
Specific Function
Catalyzes the oxidative deamination of a wide range of aliphatic and aromatic amines.
Gene Name
qhnDH
Uniprot ID
Q8VUS8
Uniprot Name
Quinohemoprotein amine dehydrogenase subunit gamma
Molecular Weight
8965.865 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]
Details6. Quinohemoprotein amine dehydrogenase 60 kDa subunit
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8VUT0
Uniprot Name
Quinohemoprotein amine dehydrogenase 60 kDa subunit
Molecular Weight
54998.075 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]
Details7. Quinohemoprotein amine dehydrogenase 40 kDa subunit
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8VUS7
Uniprot Name
Quinohemoprotein amine dehydrogenase 40 kDa subunit
Molecular Weight
39051.235 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 21:33 / Updated at June 12, 2020 16:52