3,3'-Diindolylmethane

Details

• Internal ID: 6190e994-d01b-4eaf-ad0c-9ebbf53aaf20
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: 3-(1H-indol-3-ylmethyl)-1H-indole
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43
• InChI: InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
• InChI Key: VFTRKSBEFQDZKX-UHFFFAOYSA-N
• Popularity: 804 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄N₂
• Molecular Weight: 246.31 g/mol
• Exact Mass: 246.115698455 g/mol
• Topological Polar Surface Area (TPSA): 31.60 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 0
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 1968-05-4
• diindolylmethane
• 3,3'-Methylenebis-1H-indole
• 1H-Indole, 3,3'-methylenebis-
• 3-(1H-indol-3-ylmethyl)-1H-indole
• 3,3'-Diindolymethane
• 3,3'-methylenebis(1H-indole)
• SSZ9HQT61Z
• CCRIS 5806
• CHEBI:50182
• Di-Indoly Methane
• DIM-Plus
• DIMPRO
• RefChem:484983
• 2,2'-methylenebis(1H-indole)
• di(1H-indol-3-yl)methane
• 3,3'-Methylenediindole
• DIM
• ARUNDINE
• 3,3-Diindolylmethane
• 33'-Diindolylmethane
• Plant Indole
• MFCD00195766
• Di(3-indolyl)methane
• 3,3'-methanediylbis(1H-indole)
• Bis (3-indolyl)methane
• bis-1H-indol-3-ylmethane
• 3,3 inverted exclamation marka-Diindolylmethane
• 3,3,-diindolylmethane
• 3,3-Methylenediindole
• 3,3'-Di-indolylmethane
• Diidolylmethane
• Infemin
• 3-(1H-Indol-3-ylmethyl)-1H-indole;3,3'-Methylenebis-1H-indole
• DTXSID8037047
• 33diindolylmethyle
• Di-3-indolylmethane
• NSC708486
• 3-3-diindolylmethane
• Spectrum2_001711
• Spectrum3_001989
• Spectrum5_001955
• UNII-SSZ9HQT61Z
• DIM;Arundine;HB 236
• CBiol_001839
• Oprea1_472633
• Oprea1_740951
• BSPBio_001290
• BSPBio_003589
• CBDivE_010856
• KBioGR_000010
• KBioSS_000010
• MLS006011847
• SCHEMBL325162
• SPECTRUM1505331
• SPBio_001722
• 3-3'-DIINDOLYLMETHANE
• 3,3'-di(indol-3-yl)methane
• BML3-F11
• CHEMBL446452
• orb1304763
• DIINDOLYLMETHANE [VANDF]
• SCHEMBL17506602
• SCHEMBL27821745
• 3,3'-Diindolymethane (natural)
• GTPL11208
• KBio2_000010
• KBio2_002578
• KBio2_005146
• KBio3_000019
• KBio3_000020
• KBio3_003002
• 3,3'-Diindolymethane (synthetic)
• Bio1_000125
• Bio1_000614
• Bio1_001103
• Bio2_000010
• Bio2_000490
• DIINDOLYLMETHANE, 3,3'-
• HMS1361A12
• HMS1791A12
• HMS1989A12
• HMS3402A12
• 3,3'-Diindolylmethane (Standard)
• ALBB-016048
• BCP00470
• CCG-39861
• GR-207
• HB 236
• HSCI1_000069
• HY-15758R
• s4728
• STK263696
• AKOS003627372
• CS-1652
• DB11875
• FD14886
• FD14887
• KS-5266
• NSC-708486
• SB16901
• IDI1_033760
• 3,3'-DIINDOLYLMETHANE [WHO-DD]
• NCGC00095348-01
• NCGC00095348-02
• NCGC00095348-03
• NCGC00095348-04
• NCGC00095348-05
• NCGC00095348-06
• NCGC00095348-07
• 3-[(1H-indol-3-yl)methyl]-1H-indole
• AC-11611
• HY-15758
• NCI60_038418
• SMR001828114
• SY038972
• 3,3'-Diindolylmethane, >=98% (HPLC)
• 3,3'-Diindolylmethane, analytical standard
• DB-011102
• M1399
• NS00026401
• EN300-1717487
• 968D054
• F024220
• Q4634053
• BRD-K37846922-001-05-2
• BRD-K37846922-001-06-0
• BRD-K37846922-001-09-4
• Z56791159
• 3,3'-Diindolylmethane;di(1H-indol-3-yl)methane ;3,3'-methylene-bisindole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.7375	73.75%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4595	45.95%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9497	94.97%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8305	83.05%
P-glycoprotein inhibitior	-	0.8491	84.91%
P-glycoprotein substrate	-	0.9516	95.16%
CYP3A4 substrate	-	0.6433	64.33%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	+	0.4722	47.22%
CYP3A4 inhibition	+	0.6963	69.63%
CYP2C9 inhibition	+	0.7706	77.06%
CYP2C19 inhibition	+	0.8395	83.95%
CYP2D6 inhibition	+	0.9344	93.44%
CYP1A2 inhibition	+	0.8739	87.39%
CYP2C8 inhibition	-	0.8434	84.34%
CYP inhibitory promiscuity	+	0.9063	90.63%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6095	60.95%
Eye corrosion	-	0.9829	98.29%
Eye irritation	+	0.6069	60.69%
Skin irritation	-	0.6504	65.04%
Skin corrosion	-	0.9199	91.99%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7468	74.68%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8320	83.20%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6982	69.82%
Acute Oral Toxicity (c)	III	0.6239	62.39%
Estrogen receptor binding	+	0.9857	98.57%
Androgen receptor binding	-	0.6565	65.65%
Thyroid receptor binding	+	0.7342	73.42%
Glucocorticoid receptor binding	+	0.8061	80.61%
Aromatase binding	+	0.9501	95.01%
PPAR gamma	+	0.8932	89.32%
Honey bee toxicity	-	0.8442	84.42%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.7363	73.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3714079	Q9NQS5	G-protein coupled receptor 84	252 nM	EC50	via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM; 19952.6 nM; 22387.2 nM; 17782.8 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.50%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.76%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.61%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.52%	93.99%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	88.49%	90.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	87.02%	88.56%
CHEMBL2581	P07339	Cathepsin D	85.84%	98.95%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	85.61%	83.10%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.12%	89.62%
CHEMBL255	P29275	Adenosine A2b receptor	80.35%	98.59%

Plants that contains it

• Arundina graminifolia
• Arundo donax

Cross-Links

• PubChem: 3071
• NPASS: NPC288838
• ChEMBL: CHEMBL446452
• LOTUS: LTS0186520
• wikiData: Q4634053