Indole

  • GreenMolBD CID : 67
  • Molecular Formula : C8H7N
  • Molecular Weight : 117.151
  • Exact Molecular Mass : 117.058
  • IUPAC Name : 1H-indole
  • InChI : InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
  • InChI Key : SIKJAQJRHWYJAI-UHFFFAOYSA-N
  • Canonical SMILES : C1=CC=C2C(=C1)C=CN2
  • Isomeric SMILES : c1ccc2c(c1)cc[nH]2
  • Cross Reference  Pubchem

1. Classification

1.1. 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.

1.2. Taxonomy Tree

1.3. Alternative Parent

Benzenoids; Pyrroles; Heteroaromatic compounds; Azacyclic compounds; Organopnictogen compounds; Organonitrogen compounds; Hydrocarbon derivatives;

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

Indole; Benzenoid; Heteroaromatic compound; Pyrrole; Azacycle; Organic nitrogen compound; Organopnictogen compound; Hydrocarbon derivative; Organonitrogen compound; Aromatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
2.1679 15.79 1 1 9 0 9 10 3.82987 174.218 121.277 0.67244

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
36.749814 2.04 -4.084 -8.32084 0.15308 4.237

4. Compound Reactivity

DLP nRFG nLMR
5 0 0

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Mutagen Non-Toxic 0.351673 4651.08 0.0386761 Mild None Severe Non-Degradable 0.0113291 0.410741

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes Yes Yes

7. Synonyms

Name
indole
1H-Indole
120-72-9
2,3-Benzopyrrole
Indol
1-Benzazole
Ketole
1-Azaindene
Benzopyrrole
2,3-Benzopyrole
Caswell No. 498B
Indol [German]
Indole (natural)
1-Benzo(b)pyrrole
1H-Benzo[b]pyrrole
FEMA No. 2593
CCRIS 4421
HSDB 599
EPA Pesticide Chemical Code 025000
Benzo[b]pyrrole
UNII-8724FJW4M5
AI3-01540
NSC 1964
EINECS 204-420-7
CHEMBL15844
CHEBI:16881
SIKJAQJRHWYJAI-UHFFFAOYSA-N
MFCD00005607
NCGC00167539-01
DSSTox_CID_737
DSSTox_RID_75761
DSSTox_GSID_20737
IND
CAS-120-72-9
benzazole
indolyl
1-H-indole
Indole, 7
1H-indol-1-yl
Indole (8CI)
Indole (white flake)
Indole, 98%
1H-Indole (9CI)
Indole, >=99%
SCHEMBL698
2,3-Benzopyrrole, ketole
bmse000097
Indole, 99% 50g
Indole, analytical standard
AC1L1A1Q
AC1Q4W0V
Indole, >=99%, FG
WLN: T56 BMJ
KSC175K9T
BIDD:GT0304
SCHEMBL940818
ACMC-209a84
INDOLE BENZO-PYRROLE
SCHEMBL1921769
SCHEMBL9559244
DTXSID0020737
CTK0H5599
NSC1964
185l
MolPort-001-738-532
8724FJW4M5
BB_NC-2223
NSC-1964
STR01201
Tox21_112536
Tox21_201677
Tox21_302937
ANW-17522
BBL011739
BDBM50094702
SBB055980
STL163380
ZINC14516984
AKOS000119629
Tox21_112536_1
CG-0501
CS-W001132
DB04532
Indole, puriss., >=98.5% (GC)
LS-2832
MCULE-9442796928
RP19282
RTR-003417
TRA0047977
KS-0000011Z
NCGC00167539-02
NCGC00167539-03
NCGC00256348-01
NCGC00259226-01
AJ-64954
AK105886
AN-22831
BP-10563
CJ-14563
HE009164
HE115567
HE299716
HE301357
I908
KB-12260
LS-82069
SC-19025
AB1009465
ST2408915
TR-003417
FT-0627211
I0021
ST51046571
5189-EP2269978A2
5189-EP2269985A2
5189-EP2269991A2
5189-EP2270006A1
5189-EP2270010A1
5189-EP2270011A1
5189-EP2270505A1
5189-EP2272491A1
5189-EP2272509A1
5189-EP2272517A1
5189-EP2272813A2
5189-EP2272832A1
5189-EP2272972A1
5189-EP2272973A1
5189-EP2275105A1
5189-EP2275395A2
5189-EP2275401A1
5189-EP2275412A1
5189-EP2275420A1
5189-EP2277858A1
5189-EP2277862A2
5189-EP2277872A1
5189-EP2277874A1
5189-EP2279183A1
5189-EP2279184A1
5189-EP2280000A1
5189-EP2280008A2
5189-EP2280012A2
5189-EP2281563A1
5189-EP2281815A1
5189-EP2281818A1
5189-EP2281824A1
5189-EP2284150A2
5189-EP2284151A2
5189-EP2284152A2
5189-EP2284153A2
5189-EP2284155A2
5189-EP2284156A2
5189-EP2284157A1
5189-EP2284158A1
5189-EP2284164A2
5189-EP2284920A1
5189-EP2287140A2
5189-EP2287148A2
5189-EP2287150A2
5189-EP2287155A1
5189-EP2287165A2
5189-EP2287166A2
5189-EP2289510A1
5189-EP2289871A1
5189-EP2289890A1
5189-EP2292586A2
5189-EP2292590A2
5189-EP2292592A1
5189-EP2292593A2
5189-EP2292604A2
5189-EP2292606A1
5189-EP2292611A1
5189-EP2292620A2
5189-EP2292630A1
5189-EP2295409A1
5189-EP2295419A2
5189-EP2295429A1
5189-EP2295432A1
5189-EP2295433A2
5189-EP2295503A1
5189-EP2298732A1
5189-EP2298737A1
5189-EP2298738A1
5189-EP2298740A1
5189-EP2298755A1
5189-EP2298764A1
5189-EP2298765A1
5189-EP2298766A1
5189-EP2298767A1
5189-EP2298770A1
5189-EP2298774A1
5189-EP2301536A1
5189-EP2301538A1
5189-EP2301912A2
5189-EP2301913A1
5189-EP2301914A1
5189-EP2301916A2
5189-EP2301918A1
5189-EP2301921A1
5189-EP2301923A1
5189-EP2301926A1
5189-EP2301931A1
5189-EP2301933A1
5189-EP2301937A1
5189-EP2305219A1
5189-EP2305250A1
5189-EP2305637A2
5189-EP2305640A2
5189-EP2305643A1
5189-EP2305644A1
5189-EP2305648A1
5189-EP2305651A1
5189-EP2305653A1
5189-EP2305657A2
5189-EP2305658A1
5189-EP2305695A2
5189-EP2305696A2
5189-EP2305697A2
5189-EP2305698A2
5189-EP2305808A1
5189-EP2308510A1
5189-EP2308562A2
5189-EP2308832A1
5189-EP2308839A1
5189-EP2308840A1
5189-EP2308848A1
5189-EP2308849A1
5189-EP2308850A1
5189-EP2308854A1
5189-EP2308863A1
5189-EP2308867A2
5189-EP2308870A2
5189-EP2308871A1
5189-EP2311455A1
5189-EP2311796A1
5189-EP2311797A1
5189-EP2311798A1
5189-EP2311799A1
5189-EP2311808A1
5189-EP2311825A1
5189-EP2311827A1
5189-EP2311829A1
5189-EP2311830A1
5189-EP2311831A1
5189-EP2311842A2
5189-EP2314575A1
5189-EP2314576A1
5189-EP2314587A1
5189-EP2314588A1
5189-EP2315303A1
5189-EP2316452A1
5189-EP2316459A1
5189-EP2316470A2
5189-EP2316824A1
5189-EP2316832A1
5189-EP2316833A1
5189-EP2316836A1
5189-EP2316974A1
5189-EP2371811A2
5189-EP2371831A1
5189-EP2372017A1
5189-EP2372804A1
5189-EP2374454A1
5189-EP2378585A1
C00463
I-0800
I-0810
W-1785
46560-EP2275412A1
46560-EP2287158A1
46560-EP2287159A1
46560-EP2308871A1
46560-EP2311826A2
56185-EP2289892A1
56185-EP2298738A1
56185-EP2308871A1
Indole, 9CI, 8CI
N-(4-Methylbenzenesulfonyl)
SR-01000944736
I14-3233
SR-01000944736-1
Z57833933
F2190-0647
InChI=1/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Indole
Abelmoschus esculentus (L.) Moench Pod 3
Colocasia esculenta Linn. Cormel 5
Cuscuta reflexa Whole Plant 2
Jasminum graniflorum Flower 3 , 4 , 20
Jasminum sambac L. Flower 8 , 6
Luffa acutangula Flower 3
Tamarindus indica Fruit 9

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
96 Adenosine kinase Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4UUJ 3000000 11123986
96 Adenosine kinase Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 3000000 10.1021/jm040031v 15214773
56 androgen receptor AR Homo sapiens 2.3941 1259243
56 androgen receptor AR Homo sapiens 27.306 1259243
24 aryl hydrocarbon receptor AHR Homo sapiens 22.5385 743122
24 aryl hydrocarbon receptor AHR Homo sapiens 27.306 743085
24 aryl hydrocarbon receptor AHR Homo sapiens 27.9132 743122
24 aryl hydrocarbon receptor AHR Homo sapiens 30.14 743085
7 carbonic anhydrase 1 CA1 Homo sapiens 27.4 644084
9 carbonic anhydrase 2 CA2 Homo sapiens 32.5 644085
97 Carbonic anhydrase 3 Bos taurus 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 17600 10.1016/j.ejmech.2011.12.022 22245047
97 Carbonic anhydrase 3 CA3 Bos taurus 17.6 644088
10 carbonic anhydrase 4 CA4 Homo sapiens 2.33 644086
22 carbonic anhydrase 6 CA6 Homo sapiens 3.63 644087
98 Carbonic anhydrase 6 (CA VI) Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 3630 10.1016/j.ejmech.2011.12.022 22245047
99 Carbonic Anhydrase I Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 27400 10.1016/j.ejmech.2011.12.022 22245047
100 Carbonic Anhydrase II Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 32500 10.1016/j.ejmech.2011.12.022 22245047
101 Carbonic Anhydrase IV Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 2330 10.1016/j.ejmech.2011.12.022 22245047
57 estrogen receptor 1 ESR1 Homo sapiens 30.14 1259244
49 estrogen receptor 2 ESR2 Homo sapiens 53.5974 1259378
49 estrogen receptor 2 ESR2 Homo sapiens 26.8623 1259377
25 estrogen related receptor alpha ESRRA Homo sapiens 0.8495 1224842
25 estrogen related receptor alpha ESRRA Homo sapiens 2.3941 1224848
25 estrogen related receptor alpha ESRRA Homo sapiens 2.3941 1224849
25 estrogen related receptor alpha ESRRA Homo sapiens 2.6862 1224841
25 estrogen related receptor alpha ESRRA Homo sapiens 3.38177 1259401
26 GLI family zinc finger 3 GLI3 Homo sapiens 6.0137 1259369
92 histone H2AX LOC100757539 Cricetulus griseus 99.1214 1224845
82 hypoxia inducible factor 1 subunit alpha HIF1A Homo sapiens 5.4062 1224846
102 Integrin beta-2/Leukocyte adhesion glycoprotein LFA-1 alpha Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 300000 11312920
102 Integrin beta-2/Leukocyte adhesion glycoprotein LFA-1 alpha Homo sapiens 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 300000 10.1021/jm040031v 15214773
103 integrin subunit alpha L ITGAL Homo sapiens 300 99593
104 integrin subunit beta 2 ITGB2 Homo sapiens 300 99593
105 intercellular adhesion molecule 1 ICAM1 Homo sapiens 300 99593
60 intracellular N-acetyl muramidase; lysis from within e Enterobacteria phage T4 290 238119
85 Jun proto-oncogene, AP-1 transcription factor subunit JUN Homo sapiens 2.4148 1159526
61 Lysozyme(L99A) 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 290000 10.1021/jm0491187 15916423
80 nuclear receptor subfamily 1 group I member 3 NR1I3 Homo sapiens 8.01943 1224893
80 nuclear receptor subfamily 1 group I member 3 NR1I3 Homo sapiens 13.4631 1224839
80 nuclear receptor subfamily 1 group I member 3 NR1I3 Homo sapiens 15.1058 1224838
55 nuclear receptor subfamily 3 group C member 1 NR3C1 Homo sapiens 2.6832 720692
50 RAR-related orphan receptor gamma Rorc Mus musculus 1.3463 1159521
50 RAR-related orphan receptor gamma Rorc Mus musculus 6.37006 1159523
51 retinoic acid receptor alpha RARA Homo sapiens 61.1306 1159553
51 retinoic acid receptor alpha RARA Homo sapiens 9.5311 1159552
51 retinoic acid receptor alpha RARA Homo sapiens 27.306 1159555
54 retinoid X receptor alpha RXRA Homo sapiens 6.42523 1159531
54 retinoid X receptor alpha RXRA Homo sapiens 8.5682 1159527
47 thyroid hormone receptor beta Thrb Rattus norvegicus 15.1058 743065
47 thyroid hormone receptor beta Thrb Rattus norvegicus 17.9533 743067
47 thyroid hormone receptor beta Thrb Rattus norvegicus 27.306 743065
106 Trp Aprorepressor Escherichia coli 185L,1EG9,1L4H,1O7N,1UUV,2B24,2P85,2XVJ,3Q8I,3SNM,4EAN,4PEN,4UUJ 2.51E+4 3549712

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
252372102AHH Chemical co.,ltdSource URLSource DetailMT-15743Source Record URL
187559858Key Organics/BIONETSource URLSource DetailCG-0501Source Record URL
249741925Key Organics/BIONETSource URLSource DetailSTR01201Source Record URL
3562654371717 CheMall CorporationSource URLSource DetailBG00599987Source Record URL
3627515031717 CheMall CorporationSource URLSource DetailBG04437029Source Record URL
3603139071717 CheMall CorporationSource URLSource DetailBG07155195Source Record URL
3603139231717 CheMall CorporationSource URLSource DetailBG07155211Source Record URL
3603148191717 CheMall CorporationSource URLSource DetailBG07156107Source Record URL
312597670Oakwood ProductsSource URLSource Detail068792Source Record URL
160785023AnwardSource URLSource DetailANW-17522Source Record URL
316396480abcr GmbHSource URLSource DetailAB117359Source Record URL
321906702AcadechemSource URLSource DetailACDS-018014Source Record URL
223656250AN PharmaTechSource URLSource DetailAN-22831Source Record URL
252404719MolepediaSource URLSource DetailM90004362PSource Record URL
275890560BePharm Ltd.Source URLSource DetailB134598Source Record URL
126607465ChemMolSource URLSource Detail2000372Source Record URL
126676960ChemMolSource URLSource Detail49415609Source Record URL
126606543ChemMolSource URLSource Detail83600164Source Record URL
135709498ChemMolSource URLSource Detail96707561Source Record URL
315493096Achemo Scientific LimitedSource URLSource DetailAC-44702Source Record URL
7888404SMIDSource URLSource DetailINDSource Record URL
24856309Sigma-AldrichSource URLSource Detail269077_ALDRICHSource Record URL
24867930Sigma-AldrichSource URLSource Detail442619_SUPELCOSource Record URL
329758278Sigma-AldrichSource URLSource Detail57190_SIALSource Record URL
24896037Sigma-AldrichSource URLSource DetailI3408_ALDRICHSource Record URL
24901173Sigma-AldrichSource URLSource DetailW259306_ALDRICHSource Record URL
346401696King ScientificSource URLSource DetailKS-0000011ZSource Record URL
163802791King ScientificSource URLSource DetailKSC175K9TSource Record URL
162284897AchemicaSource URLSource DetailACMC-209a84Source Record URL
143501070BroadPharmSource URLSource DetailBP-10563Source Record URL
250213551Founder PharmaSource URLSource DetailFD29439Source Record URL
319561032AbovChem LLCSource URLSource DetailAC130112Source Record URL
251891077labseekerSource URLSource DetailSC-19025Source Record URL
312626214BiocoreSource URLSource DetailBIE056933Source Record URL
136896980Tetrahedron Scientific IncSource URLSource Detail8174Source Record URL
292897315Aurora Fine Chemicals LLCSource URLSource DetailA00.156.625Source Record URL
276776340Aurora Fine Chemicals LLCSource URLSource DetailK02.109.043Source Record URL
374150596AA BLOCKSSource URLSource DetailAA000PYXSource Record URL
143430539TimTecSource URLSource DetailSBB055980Source Record URL
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355173753MuseChemSource URLSource DetailR051188Source Record URL
125326400Vitas-M LaboratorySource URLSource DetailBBL011739Source Record URL
125292445Vitas-M LaboratorySource URLSource DetailSTL163380Source Record URL
49747778BiosynthSource URLSource DetailI-0800Source Record URL
49747779BiosynthSource URLSource DetailI-0810Source Record URL
310275198Glentham Life Sciences Ltd.Source URLSource DetailGK0968Source Record URL
163749048Nanjing KaimuboSource URLSource DetailKB-12260Source Record URL
57320493NovoSeekSource URLSource Detail798Source Record URL
3133537ChemExper Chemical DirectorySource URLSource DetailHiV@@@RfU|kahDB@@@Source Record URL
318307392Chem-Space.com DatabaseSource URLSource DetailCSC000188412Source Record URL
88781517MolPortSource URLSource DetailMolPort-001-738-532Source Record URL
252034913Bide Pharmatech Ltd.Source URLSource DetailBD134598Source Record URL
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104668052AKos Consulting & SolutionsSource URLSource DetailAKOS000119629Source Record URL
340511240LGC StandardsSource URLSource DetailDRE-C20831000Source Record URL
334359393EnamineSource URLSource DetailZ57833933Source Record URL
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204936683TractusSource URLSource DetailTR-003417Source Record URL
252273161TractusSource URLSource DetailTRA0047977Source Record URL
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85088685MP BiomedicalsSource URLSource Detail101000Source Record URL
85086940MP BiomedicalsSource URLSource Detail102036Source Record URL
186006696Aurum Pharmatech LLCSource URLSource DetailW-1785Source Record URL
125311905ABBLIS ChemicalsSource URLSource DetailAB1009465Source Record URL
315361022Life ChemicalsSource URLSource DetailF2190-0647Source Record URL
169537708MculeSource URLSource DetailMCULE-9442796928Source Record URL
164811100Finetech Industry LimitedSource URLSource DetailFT-0627211Source Record URL
87245423ISpharmSource URLSource DetailI14-3233Source Record URL
319481467eNovation ChemicalsSource URLSource DetailD541069Source Record URL
249779536Day BiochemSource URLSource DetailDAYBIOCHEM30742Source Record URL
318040722iChemical Technology USA IncSource URLSource DetailEBD38013Source Record URL
249829323SyntreeSource URLSource DetailST2408915Source Record URL
347729045Yuhao ChemicalSource URLSource DetailSY0038Source Record URL
250182398Green Chempharm IncSource URLSource Detail50-9924Source Record URL
163304373ChemTikSource URLSource DetailCTK0H5599Source Record URL
342403922Wubei-BiochemSource URLSource DetailWB053927SUSource Record URL
315445214Phion LtdSource URLSource Detail25283900Source Record URL
223574125A&J Pharmtech CO., LTD.Source URLSource DetailAJ-64954Source Record URL
223499917A&J Pharmtech CO., LTD.Source URLSource DetailCJ-14563Source Record URL
316605730ParchemSource URLSource Detail8325Source Record URL
160967536Chembase.cnSource URLSource Detail4103Source Record URL
348624570Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0142721Source Record URL
329733822VladaChemSource URLSource DetailVL142803Source Record URL
104295883ABI ChemSource URLSource DetailAC1L1A1QSource Record URL
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277288269MolCoreSource URLSource DetailCS11496Source Record URL
255422354OXCHEM CORPORATIONSource URLSource DetailAX8134598Source Record URL
87571430TCI (Tokyo Chemical Industry)Source URLSource DetailI0021Source Record URL
312280181NORRIS PHARMSource URLSource DetailTH-C13250Source Record URL
253663511Pure chemistrySource URLSource Detail814533Source Record URL
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273013283ChemShuttleSource URLSource Detail128622Source Record URL
254764430Boc SciencesSource URLSource Detail120-72-9Source Record URL
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174550436WutechSource URLSource DetailRP19282Source Record URL