3,4-dimethoxy-6-(2'-N,N-dimethylaminoethyl)-5-(methylthio)benzotrithiane

ID: ALA222469

PubChem CID: 9997973

Max Phase: Preclinical

Molecular Formula: C13H19NO2S4

Molecular Weight: 349.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(OC)c2c(c(CCN(C)C)c1SC)SSS2

Standard InChI:  InChI=1S/C13H19NO2S4/c1-14(2)7-6-8-11(17-5)9(15-3)10(16-4)13-12(8)18-20-19-13/h6-7H2,1-5H3

Standard InChI Key:  VDPRVSQPQCVGDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -2.5931  -21.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5943  -22.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8794  -23.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812  -21.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659  -21.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1610  -22.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3691  -22.9087    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155  -22.2335    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770  -21.5641    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8804  -23.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953  -24.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962  -25.1311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3111  -25.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822  -25.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837  -20.5914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077  -21.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0220  -21.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1705  -20.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3091  -23.0684    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0232  -22.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  3 10  1  0
  5  6  1  0
 10 11  1  0
 11 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
  4 15  1  0
  5  4  2  0
  1 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 15 18  1  0
  8  9  1  0
  2 19  1  0
  9  5  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA222469

   2-(4,5-dimethoxy-6-methylsulfanyl-1,2,3-benzotrithiol-7-yl)-N,N-dimethylethanamine

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: 349.57

Molecular Weight (Monoisotopic): 349.0299

AlogP: 4.29

#Rotatable Bonds: 6

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.73

CX LogP: 3.74

CX LogD: 2.39

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.56

Np Likeness Score: 1.04

References

1. Nakazawa T, Xu J, Nishikawa T, Oda T, Fujita A, Ukai K, Mangindaan RE, Rotinsulu H, Kobayashi H, Namikoshi M..  (2007)  Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium.,  70  (3): [PMID:17269824] [10.1021/np060593c]

2. Davison EK, Sperry J..  (2017)  Natural Products with Heteroatom-Rich Ring Systems.,  80  (11): [PMID:29135244] [10.1021/acs.jnatprod.7b00575]

Source

Source(1):

• Scientific Literature