di-(2-ethylhexyl) phthalate

ID: ALA402794

PubChem CID: 7057919

Max Phase: Preclinical

Molecular Formula: C24H38O4

Molecular Weight: 390.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Di-(2-Ethylhexyl) Phthalate | Diethylhexylphthalate | Diethylhexylphthalate|Di-(2-ethylhexyl) phthalate|CHEMBL402794|BDBM50371947|1-O-[(2S)-2-ethylhexyl] 2-O-[(2R)-2-ethylhexyl] benzene-1,2-dicarboxylate

Canonical SMILES:  CCCC[C@@H](CC)COC(=O)c1ccccc1C(=O)OC[C@@H](CC)CCCC

Standard InChI:  InChI=1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3/t19-,20+

Standard InChI Key:  BJQHLKABXJIVAM-BGYRXZFFSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  1  0  0  0  0  0999 V2000
    1.4100   -6.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087   -7.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217   -7.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -7.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379   -6.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197   -5.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5502   -5.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2668   -6.2037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462   -4.9698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5559   -7.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566   -8.2787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2700   -7.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9847   -7.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -4.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -4.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -4.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2546   -3.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4040   -4.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163   -4.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8328   -4.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6988   -7.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4137   -7.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6980   -6.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4121   -5.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1277   -7.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8425   -7.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5566   -7.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  7  1  0
 10 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 15 17  1  1
 17 18  1  0
  7  9  2  0
 16 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 20 21  1  0
  2  3  1  0
 14 22  1  0
  4 11  1  0
 22 23  1  0
  5  6  2  0
 22 24  1  6
 11 12  2  0
 24 25  1  0
  6  1  1  0
 23 26  1  0
 11 13  1  0
 26 27  1  0
  1  2  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA402794

   BIS(2-ETHYLHEXYL)PHTHALATE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 390.56

Molecular Weight (Monoisotopic): 390.2770

AlogP: 6.43

#Rotatable Bonds: 14

Polar Surface Area: 52.60

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 8.03

CX LogD: 8.03

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.34

Np Likeness Score: 0.09

References

1. Hoang VL, Li Y, Kim SK..  (2008)  Cathepsin B inhibitory activities of phthalates isolated from a marine Pseudomonas strain.,  18  (6): [PMID:18289850] [10.1016/j.bmcl.2008.01.097]

2. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

3. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

4. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

5. Cherrington NJ, Hartley DP, Li N, Johnson DR, Klaassen CD..  (2002)  Organ distribution of multidrug resistance proteins 1, 2, and 3 (Mrp1, 2, and 3) mRNA and hepatic induction of Mrp3 by constitutive androstane receptor activators in rats.,  300  (1): [PMID:11752103] [10.1124/jpet.300.1.97]

6. Guo GL, Choudhuri S, Klaassen CD..  (2002)  Induction profile of rat organic anion transporting polypeptide 2 (oatp2) by prototypical drug-metabolizing enzyme inducers that activate gene expression through ligand-activated transcription factor pathways.,  300  (1): [PMID:11752118] [10.1124/jpet.300.1.206]

7. DrugMatrix,  [10.6019/CHEMBL3885881]

Source

Source(3):

• Scientific Literature
• DrugMatrix
• TP-search Transporter Database