Doxorubicin 14-[4-(5-Thioxo-5H-[1,2]dithiol-3-yl)phenoxy]-acetate hydrochloride

ID: ALA3819100

PubChem CID: 127050651

Max Phase: Preclinical

Molecular Formula: C38H36ClNO13S3

Molecular Weight: 809.89

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES: COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)COC(=O)COc1ccc(-c2cc(=S)ss2)cc1)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl

Standard InChI: InChI=1S/C38H35NO13S3.ClH/c1-16-33(42)21(39)10-27(51-16)52-23-13-38(47,25(40)14-50-26(41)15-49-18-8-6-17(7-9-18)24-11-28(53)55-54-24)12-20-30(23)37(46)32-31(35(20)44)34(43)19-4-3-5-22(48-2)29(19)36(32)45;/h3-9,11,16,21,23,27,33,42,44,46-47H,10,12-15,39H2,1-2H3;1H/t16-,21-,23-,27-,33+,38-;/m0./s1

Standard InChI Key: YOSGFJUSPGIYCP-QVUJIKCZSA-N

Molfile:

     RDKit          2D

 57 62  0  0  0  0  0  0  0  0999 V2000
    7.0730   -4.4494    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5671    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5671   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923    2.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923   -3.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8010   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8010    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070    2.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070   -3.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2722   -3.5199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122   -4.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8029   -2.7279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0594   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3993    0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9922   -1.7529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6553   -0.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7778    1.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769   -4.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1972   -4.9363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2428   -6.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9671   -7.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6459   -6.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6003   -5.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2998   -7.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0036   -8.4242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6254   -7.1459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251   -2.4979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9952   -0.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2512   -0.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0624    1.1738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5911   -0.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8471   -0.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.1873   -0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4409   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.3543   -2.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0142   -3.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7606   -2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.6086   -3.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.9944   -2.9232    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -20.9303   -4.0955    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -20.1046   -5.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.6584   -4.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -20.5268   -6.4710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  4  2  1  0
  2 11  1  0
 10  3  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  2  0
 11 12  1  0
 12 17  2  0
 16 13  2  0
 13 10  1  0
  3 14  2  0
  2 15  2  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 13 22  1  0
 12 23  1  0
  9 24  1  0
 24 25  1  0
 18 26  1  0
 20 27  1  6
 27 28  1  0
 27 29  2  0
 28 30  1  0
 20 31  1  0
 32 26  1  1
 32 33  1  0
 32 37  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 34 38  1  6
 35 39  1  6
 36 40  1  6
 18 41  1  6
 30 42  1  0
 42 43  1  0
 42 44  2  0
 43 45  1  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  2  0
 51 46  1  0
 49 52  1  0
 52 53  1  0
 53 54  1  0
 54 55  1  0
 55 56  1  0
 56 52  2  0
 55 57  2  0
M  END

Associated Targets(Human)

Serum (1292 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

U2OS (164939 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

Discover Target: TOP2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Natural Product: No	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

Natural Product: No

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: 809.89	Molecular Weight (Monoisotopic): 809.1271	AlogP: 4.15	#Rotatable Bonds: 10
Polar Surface Area: 221.37	Molecular Species: BASE	HBA: 17	HBD: 5
#RO5 Violations: 2	HBA (Lipinski): 14	HBD (Lipinski): 6	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 8.00	CX Basic pKa: 9.03	CX LogP: 3.96	CX LogD: 3.53
Aromatic Rings: 4	Heavy Atoms: 55	QED Weighted: 0.06	Np Likeness Score: 0.94

References

1. Chegaev K, Rolando B, Cortese D, Gazzano E, Buondonno I, Lazzarato L, Fanelli M, Hattinger CM, Serra M, Riganti C, Fruttero R, Ghigo D, Gasco A.. (2016) H2S-Donating Doxorubicins May Overcome Cardiotoxicity and Multidrug Resistance., 59 (10): [PMID:27120394] [10.1021/acs.jmedchem.6b00184]

Doxorubicin 14-[4-(5-Thioxo-5H-[1,2]dithiol-3-yl)phenoxy]-acetate hydrochloride

Names and Identifiers

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source