NP-MRD: Showing NP-Card for Arundine (NP0004999)

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Record Information

Version

1.0

Created at

2020-12-09 02:22:20 UTC

Updated at

2021-07-15 16:50:46 UTC

NP-MRD ID

NP0004999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arundine

Provided By

NPAtlas

Description

3,3'-Diindolylmethane, also known as bis-1H-indol-3-ylmethane or DIM, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Arundine is found in Arundina graminifolia, Arundo donax and Vibrio parahaemolyticus. It was first documented in 2003 (PMID: 14640534). Based on a literature review a significant number of articles have been published on 3,3'-Diindolylmethane (PMID: 12665522) (PMID: 34273521) (PMID: 34221175) (PMID: 34220018) (PMID: 34150611) (PMID: 34066056).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118163D          

 33 36  0  0  0  0            999 V2000
   -3.9115    1.0765    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.9617    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    1.4794    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    0.1791   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.5156   -1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.0823   -1.8981 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2534   -0.4008   -1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106   -1.4184   -1.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -1.4644   -1.0452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755   -0.5277   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.1896    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    0.8181    1.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    1.4566    1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.1382    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.1215   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -1.8167   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -1.9191   -0.4021 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903   -0.7056    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.2296    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4504    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9148    2.9971    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    2.1988   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533   -0.4299   -2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    1.0567   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -2.0241   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -2.1265   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -0.6988    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795    1.0963    2.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    2.2521    2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    1.6380    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -2.6482   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -2.7739   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619   -0.9494    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19  1  1  0  0  0  0
 18  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
  1 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 22  1  0  0  0  0
  6 23  1  0  0  0  0
  6 24  1  0  0  0  0
  8 25  1  0  0  0  0
  9 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 14 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 32  1  0  0  0  0
 19 33  1  0  0  0  0
M  END

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.9115    1.0765    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.9617    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    1.4794    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    0.1791   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.5156   -1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.0823   -1.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534   -0.4008   -1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106   -1.4184   -1.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -1.4644   -1.0452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755   -0.5277   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.1896    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    0.8181    1.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    1.4566    1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.1382    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.1215   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -1.8167   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -1.9191   -0.4021 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903   -0.7056    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.2296    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4504    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9148    2.9971    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    2.1988   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533   -0.4299   -2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    1.0567   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -2.0241   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -2.1265   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -0.6988    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795    1.0963    2.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    2.2521    2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    1.6380    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -2.6482   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -2.7739   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619   -0.9494    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  1  1  0
 18  4  1  0
 15  7  1  0
 15 10  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END


  Mrv1652306242118163D          

 33 36  0  0  0  0            999 V2000
   -3.9115    1.0765    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.9617    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    1.4794    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    0.1791   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.5156   -1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.0823   -1.8981 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2534   -0.4008   -1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106   -1.4184   -1.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -1.4644   -1.0452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755   -0.5277   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.1896    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    0.8181    1.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    1.4566    1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.1382    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.1215   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -1.8167   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -1.9191   -0.4021 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903   -0.7056    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.2296    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4504    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9148    2.9971    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    2.1988   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533   -0.4299   -2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    1.0567   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -2.0241   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -2.1265   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -0.6988    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795    1.0963    2.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    2.2521    2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    1.6380    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -2.6482   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -2.7739   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619   -0.9494    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19  1  1  0  0  0  0
 18  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
  1 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 22  1  0  0  0  0
  6 23  1  0  0  0  0
  6 24  1  0  0  0  0
  8 25  1  0  0  0  0
  9 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 14 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 32  1  0  0  0  0
 19 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C17H14N2

> <MOLECULAR_WEIGHT>
246.313

> <EXACT_MASS>
246.115698459

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.88517214856524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1H-indol-3-yl)methyl]-1H-indole

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
4.262563828999999

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.180528868983043

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.516569971636592

> <JCHEM_POLAR_SURFACE_AREA>
31.58

> <JCHEM_REFRACTIVITY>
77.96820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3'-diindolylmethane

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.9115    1.0765    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.9617    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    1.4794    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    0.1791   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.5156   -1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.0823   -1.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534   -0.4008   -1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106   -1.4184   -1.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -1.4644   -1.0452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755   -0.5277   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.1896    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    0.8181    1.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    1.4566    1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.1382    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.1215   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -1.8167   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -1.9191   -0.4021 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903   -0.7056    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.2296    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4504    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9148    2.9971    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    2.1988   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533   -0.4299   -2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    1.0567   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -2.0241   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -2.1265   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -0.6988    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795    1.0963    2.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    2.2521    2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    1.6380    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -2.6482   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -2.7739   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619   -0.9494    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  1  1  0
 18  4  1  0
 15  7  1  0
 15 10  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.912   1.077   1.522  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.959   1.962   1.052  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.041   1.479   0.151  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.018   0.179  -0.303  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.247  -0.516  -1.192  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.059  -0.082  -1.898  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.253  -0.401  -1.294  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.111  -1.418  -1.782  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.222  -1.464  -1.045  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.176  -0.528  -0.070  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.067  -0.190   0.927  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.790   0.818   1.818  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.578   1.457   1.645  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.674   1.138   0.661  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.947   0.122  -0.242  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.763  -1.817  -1.240  0.00  0.00           C+0
HETATM   17  N   UNK     0      -2.820  -1.919  -0.402  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.990  -0.706   0.181  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.910  -0.230   1.082  0.00  0.00           C+0
HETATM   20  H   UNK     0      -4.630   1.450   2.226  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.915   2.997   1.366  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.314   2.199  -0.225  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.053  -0.430  -2.977  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.136   1.057  -2.035  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.826  -2.024  -2.635  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.008  -2.127  -1.202  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.021  -0.699   1.052  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.479   1.096   2.611  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.343   2.252   2.341  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.744   1.638   0.528  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.412  -2.648  -1.837  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.398  -2.774  -0.232  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.662  -0.949   1.448  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   23   24                                             
CONECT    7    6    8   15                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15   30                                                  
CONECT   15   14    7   10                                                  
CONECT   16    5   17   31                                                  
CONECT   17   16   18   32                                                  
CONECT   18   17   19    4                                                  
CONECT   19   18    1   33                                                  
CONECT   20    1                                                            
CONECT   21    2                                                            
CONECT   22    3                                                            
CONECT   23    6                                                            
CONECT   24    6                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

RDKit          3D

33 36  0  0  0  0  0  0  0  0999 V2000
   -3.9115    1.0765    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.9617    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    1.4794    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177    0.1791   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466   -0.5156   -1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.0823   -1.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534   -0.4008   -1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1106   -1.4184   -1.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -1.4644   -1.0452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755   -0.5277   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.1896    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    0.8181    1.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781    1.4566    1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.1382    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.1215   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -1.8167   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -1.9191   -0.4021 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903   -0.7056    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.2296    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4504    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9148    2.9971    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    2.1988   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533   -0.4299   -2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    1.0567   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -2.0241   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -2.1265   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -0.6988    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795    1.0963    2.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    2.2521    2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    1.6380    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120   -2.6482   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -2.7739   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619   -0.9494    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  1  1  0
 18  4  1  0
 15  7  1  0
 15 10  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3,3'-Methylenebis-1H-indole	ChEBI
Bis-1H-indol-3-ylmethane	ChEBI
DIM	ChEBI
2,2'-Methylenebis(1H-indole)	HMDB
Diindolylmethane	HMDB

Chemical Formula

C₁₇H₁₄N₂

Average Mass

246.3130 Da

Monoisotopic Mass

246.11570 Da

IUPAC Name

3-[(1H-indol-3-yl)methyl]-1H-indole

Traditional Name

3,3'-diindolylmethane

CAS Registry Number

Not Available

SMILES

C(C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arundina graminifolia	LOTUS Database	35616633
Arundo donax	LOTUS Database	35616633
Vibrio parahaemolyticus	NPAtlas	14640534

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.4	ALOGPS
logP	4.26	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	16.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	31.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.97 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005249

HMDB ID

HMDB0246001

DrugBank ID

DB11875

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,3'-Diindolylmethane

METLIN ID

Not Available

PubChem Compound

3071

PDB ID

Not Available

ChEBI ID

50182

Good Scents ID

Not Available

References

General References

Veluri R, Oka I, Wagner-Dobler I, Laatsch H: New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249. J Nat Prod. 2003 Nov;66(11):1520-3. doi: 10.1021/np030288g. [PubMed:14640534 ]
Le HT, Schaldach CM, Firestone GL, Bjeldanes LF: Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells. J Biol Chem. 2003 Jun 6;278(23):21136-45. doi: 10.1074/jbc.M300588200. Epub 2003 Mar 27. [PubMed:12665522 ]
Chu M, Zheng C, Chen C, Song G, Hu X, Wang ZW: Targeting cancer stem cells by nutraceuticals for cancer therapy. Semin Cancer Biol. 2021 Jul 14. pii: S1044-579X(21)00202-9. doi: 10.1016/j.semcancer.2021.07.008. [PubMed:34273521 ]
Pillaiyar T, Sedaghati M, B Mahardhika A, L Wendt L, E Muller C: Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center. Beilstein J Org Chem. 2021 Jun 18;17:1464-1475. doi: 10.3762/bjoc.17.102. eCollection 2021. [PubMed:34221175 ]
Stainsloss I, Sankaran M, Kannaiyan P: Correction to: 3,3'-Diindolylmethane Encapsulated Chitosan Nanoparticles Accelerates Inflammatory Markers, ER/PR, Glycoprotein and Mast Cells Population During Chemical Carcinogen Induced Mammary Cancer in Rats. Indian J Clin Biochem. 2021 Jul;36(3):382-383. doi: 10.1007/s12291-021-00981-2. Epub 2021 May 25. [PubMed:34220018 ]
Xiang F, Zhu Z, Zhang M, Wang J, Chen Z, Li X, Zhang T, Gu Q, Wu R, Kang X: 3,3'-Diindolylmethane Enhances Paclitaxel Sensitivity by Suppressing DNMT1-Mediated KLF4 Methylation in Breast Cancer. Front Oncol. 2021 Jun 3;11:627856. doi: 10.3389/fonc.2021.627856. eCollection 2021. [PubMed:34150611 ]
Munakarmi S, Shrestha J, Shin HB, Lee GH, Jeong YJ: 3,3'-Diindolylmethane Suppresses the Growth of Hepatocellular Carcinoma by Regulating Its Invasion, Migration, and ER Stress-Mediated Mitochondrial Apoptosis. Cells. 2021 May 12;10(5). pii: cells10051178. doi: 10.3390/cells10051178. [PubMed:34066056 ]
Zhu WJ, Lin LP, Liu D, Qian JC, Zhou BB, Yuan DD, Tan RX: Pharmacophore-inspired discovery of FLT3 inhibitor from kimchi. Food Chem. 2021 Nov 1;361:130139. doi: 10.1016/j.foodchem.2021.130139. Epub 2021 May 18. [PubMed:34062461 ]
Vermillion Maier ML, Siddens LK, Uesugi SL, Choi J, Leonard SW, Pennington JM, Tilton SC, Smith JN, Ho E, Chow HHS, Nguyen BD, Kolluri SK, Williams DE: 3,3'-Diindolylmethane Exhibits Significant Metabolism after Oral Dosing in Humans. Drug Metab Dispos. 2021 Aug;49(8):694-705. doi: 10.1124/dmd.120.000346. Epub 2021 May 25. [PubMed:34035125 ]
Ye Y, Li X, Wang Z, Ye F, Xu W, Lu R, Shen H, Miao S: 3,3'-Diindolylmethane induces gastric cancer cells death via STIM1 mediated store-operated calcium entry. Int J Biol Sci. 2021 Mar 19;17(5):1217-1233. doi: 10.7150/ijbs.56833. eCollection 2021. [PubMed:33867841 ]
Shi H, Sun Y, Ruan H, Ji C, Zhang J, Wu P, Li L, Huang C, Jia Y, Zhang X, Xu W, Jiang J, Qian H: 3,3'-Diindolylmethane Promotes Gastric Cancer Progression via beta-TrCP-Mediated NF-kappaB Activation in Gastric Cancer-Derived MSCs. Front Oncol. 2021 Mar 24;11:603533. doi: 10.3389/fonc.2021.603533. eCollection 2021. [PubMed:33842314 ]

Showing NP-Card for Arundine (NP0004999)

MOL for NP0004999 (Arundine)

3D MOL for NP0004999 (Arundine)

3D SDF for NP0004999 (Arundine)

3D-SDF for NP0004999 (Arundine)

PDB for NP0004999 (Arundine)

3D PDB for NP0004999 (Arundine)

SMILES for NP0004999 (Arundine)

INCHI for NP0004999 (Arundine)

Structure for NP0004999 (Arundine)

3D Structure for NP0004999 (Arundine)