Identification

Name
Indole
Accession Number
DB04532  (EXPT01882)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 2593
Categories
Not Available
UNII
8724FJW4M5
CAS number
120-72-9
Weight
Average: 117.1479
Monoisotopic: 117.057849229
Chemical Formula
C8H7N
InChI Key
SIKJAQJRHWYJAI-UHFFFAOYSA-N
InChI
InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
IUPAC Name
1H-indole
SMILES
N1C=CC2=C1C=CC=C2

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULysozymeNot AvailableEnterobacteria phage T4
UNicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Tryptophan MetabolismMetabolic
Tryptophan MetabolismMetabolic
Tryptophan Metabolism IIMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Ernst Schefczik, "Preparation of indole derivatives." U.S. Patent US4611064, issued June, 1900.

US4611064
General References
Not Available
External Links
Human Metabolome Database
HMDB0000738
KEGG Compound
C00463
PubChem Compound
798
PubChem Substance
46508707
ChemSpider
776
BindingDB
50094702
ChEBI
16881
ChEMBL
CHEMBL15844
HET
IND
Wikipedia
Indole
PDB Entries
185l / 1eg9 / 1l4h / 1o7n / 1uuv / 2b24 / 2p85 / 2xvj / 3q8i / 3snm
show 5 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)52.5 °CPhysProp
boiling point (°C)254 °CPhysProp
water solubility3560 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.14HANSCH,C ET AL. (1995)
logS-1.52ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility5.31 mg/mLALOGPS
logP2.29ALOGPS
logP2.07ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.14 m3·mol-1ChemAxon
Polarizability12.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9884
Caco-2 permeable+0.5053
P-glycoprotein substrateNon-substrate0.8309
P-glycoprotein inhibitor INon-inhibitor0.9787
P-glycoprotein inhibitor IINon-inhibitor0.9485
Renal organic cation transporterNon-inhibitor0.7941
CYP450 2C9 substrateNon-substrate0.8443
CYP450 2D6 substrateNon-substrate0.8568
CYP450 3A4 substrateNon-substrate0.7837
CYP450 1A2 substrateInhibitor0.787
CYP450 2C9 inhibitorNon-inhibitor0.5491
CYP450 2D6 inhibitorInhibitor0.6189
CYP450 2C19 inhibitorInhibitor0.7661
CYP450 3A4 inhibitorNon-inhibitor0.9449
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6191
Ames testNon AMES toxic0.8729
CarcinogenicityNon-carcinogens0.9242
BiodegradationNot ready biodegradable0.5841
Rat acute toxicity2.0376 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9498
hERG inhibition (predictor II)Non-inhibitor0.9453
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-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014i-6900000000-09af4d0af4e5f7259a59
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9800000000-4160749bd673d5e00048
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9800000000-33bf321019a6a8e3401a
Mass Spectrum (Electron Ionization)MSsplash10-014i-9700000000-3b1ec48b5bce79adb282
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-014i-0900000000-622dfed80152ea08d52a
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-9100000000-2531cceca05522a5489e
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014l-9000000000-5e07c15293929ff4440f
MS/MS Spectrum - EI-B (MX-1303) , PositiveLC-MS/MSsplash10-014i-6900000000-09af4d0af4e5f7259a59
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-014i-9800000000-4160749bd673d5e00048
MS/MS Spectrum - EI-B (HITACHI M-68) , PositiveLC-MS/MSsplash10-014i-9800000000-33bf321019a6a8e3401a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-014i-0900000000-e6b11e225744a0d85f71
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0900000000-e6b11e225744a0d85f71
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-7b49c1c370d7355c5e6f
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-050ef45f3ec404d7eb65
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-79ff95be504a5efad264
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-31ff8b484e0dc207fcc9
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-864a48552fea562fc370
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-bd82bfab4567619b5c41
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-6bff353534e6f5f9105b
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-c4e339d4a1d3fda0a949
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-100cd0cc67ac9eda3f4e
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014l-5900000000-79447b563349d08aacc0
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-00kf-9800000000-a1ce5da5416e6d003ff9
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-00kf-9500000000-1dcc90ff56b80930d454
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-00kf-9300000000-70e7382a85a822aac101
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-00kf-9200000000-25d55adc1c615e7d016f
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddb36a6cce4f103bc423
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddb36a6cce4f103bc423
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-1d2ff7e56486b9ca4c2d
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-71de1f813c37f2549be4
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-1900000000-ffbab8ee8d6ea10f6b88
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014l-4900000000-75a01f786adcdfc0442d
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-00kf-9800000000-310aef0907982c2885d7
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-00kf-9500000000-5aaacb46312595a18847
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0006-9300000000-b54d08abed2c79be3a55
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-00kf-9100000000-5897e1655f1aa0e2191e
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddac2994fff8f21fe8dd
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddac2994fff8f21fe8dd
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddac2994fff8f21fe8dd
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-2c0f27b62f220e2ee3a6
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-53afbaab2e64087b986b
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-ccfd9273f820030931d2
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014l-6900000000-be79f1ccf8a16cf5fb22
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014u-9500000000-1a5110633cd682046296
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000l-9100000000-889e7648dad637476da4
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-38d6c79fed7b04d321d5
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddac2994fff8f21fe8dd
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddac2994fff8f21fe8dd
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ddac2994fff8f21fe8dd
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-2c0f27b62f220e2ee3a6
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-53afbaab2e64087b986b
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-ccfd9273f820030931d2
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014l-6900000000-be79f1ccf8a16cf5fb22
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014u-9500000000-1a5110633cd682046296
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000l-9100000000-889e7648dad637476da4
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-38d6c79fed7b04d321d5
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
Indoles
Alternative Parents
Benzenoids / Pyrroles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Indole / Benzenoid / Heteroaromatic compound / Pyrrole / Azacycle / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Aromatic heteropolycyclic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indole, polycyclic heteroarene (CHEBI:16881) / an indole (INDOLE)

Targets

Details
1. Lysozyme
Kind
Protein
Organism
Enterobacteria phage T4
Pharmacological action
Unknown
General Function
Lysozyme activity
Specific Function
Endolysin with lysozyme activity that degrades host peptidoglycans and participates with the holin and spanin proteins in the sequential events which lead to the programmed host cell lysis releasin...
Gene Name
E
Uniprot ID
P00720
Uniprot Name
Endolysin
Molecular Weight
18691.385 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Nicotinate-nucleotide-dimethylbenzimidazole phosphoribosyltransferase activity
Specific Function
Catalyzes the synthesis of alpha-ribazole-5'-phosphate from nicotinate mononucleotide (NAMN) and 5,6-dimethylbenzimidazole (DMB).
Gene Name
cobT
Uniprot ID
Q05603
Uniprot Name
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase
Molecular Weight
36612.305 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 06:00