Doxorubicin 14-(3-allyldisulfanyl)propionate hydrochloride

ID: ALA3819034

PubChem CID: 127050041

Max Phase: Preclinical

Molecular Formula: C33H38ClNO12S2

Molecular Weight: 703.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCSSCCC(=O)OCC(=O)[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1c(OC)cccc1C3=O.Cl

Standard InChI:  InChI=1S/C33H37NO12S2.ClH/c1-4-9-47-48-10-8-22(36)44-14-21(35)33(42)12-17-25(20(13-33)46-23-11-18(34)28(37)15(2)45-23)32(41)27-26(30(17)39)29(38)16-6-5-7-19(43-3)24(16)31(27)40;/h4-7,15,18,20,23,28,37,39,41-42H,1,8-14,34H2,2-3H3;1H/t15-,18-,20-,23-,28+,33-;/m0./s1

Standard InChI Key:  AUUXPIUCDAIPPQ-FGYOMBRZSA-N

Molfile:  

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M  END

Molecule Features

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: 703.79

Molecular Weight (Monoisotopic): 703.1757

AlogP: 2.51

#Rotatable Bonds: 12

Polar Surface Area: 212.14

Molecular Species: BASE

HBA: 15

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.00

CX Basic pKa: 9.03

CX LogP: 2.94

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.06

Np Likeness Score: 1.45

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]

Source

Source(1):

• Scientific Literature