ID: ALA1834993

Max Phase: Preclinical

Molecular Formula: C28H30ClN5O7S

Molecular Weight: 616.10

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(C)CCOc1ccc2[nH]c(C(=O)N3CC(CCl)c4c3cc([N+](=O)[O-])c3cc(S(=O)(=O)NCCO)ccc43)cc2c1

Standard InChI:  InChI=1S/C28H30ClN5O7S/c1-32(2)8-10-41-19-3-6-23-17(11-19)12-24(31-23)28(36)33-16-18(15-29)27-21-5-4-20(42(39,40)30-7-9-35)13-22(21)25(34(37)38)14-26(27)33/h3-6,11-14,18,30-31,35H,7-10,15-16H2,1-2H3

Standard InChI Key:  KRUNPKDABQVLHA-UHFFFAOYSA-N

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

Properties

Molecular Weight: 616.10

Molecular Weight (Monoisotopic): 615.1554

AlogP: 3.42

#Rotatable Bonds: 11

Polar Surface Area: 158.11

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.99

CX Basic pKa: 8.72

CX LogP: 2.01

CX LogD: 0.88

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.13

Np Likeness Score: -1.17

References

1. Stevenson RJ, Denny WA, Ashoorzadeh A, Pruijn FB, van Leeuwen WF, Tercel M..  (2011)  The effect of a bromide leaving group on the properties of nitro analogs of the duocarmycins as hypoxia-activated prodrugs and phosphate pre-prodrugs for antitumor therapy.,  19  (20): [PMID:21920763] [10.1016/j.bmc.2011.08.045]

2. Stevenson RJ, Denny WA, Tercel M, Pruijn FB, Ashoorzadeh A..  (2012)  Nitro seco analogues of the duocarmycins containing sulfonate leaving groups as hypoxia-activated prodrugs for cancer therapy.,  55  (6): [PMID:22339090] [10.1021/jm201717y]

3. Tercel M, Lee HH, Mehta SY, Youte Tendoung JJ, Bai SY, Liyanage HDS, Pruijn FB..  (2017)  Influence of a Basic Side Chain on the Properties of Hypoxia-Selective Nitro Analogues of the Duocarmycins: Demonstration of Substantial Anticancer Activity in Combination with Irradiation or Chemotherapy.,  60  (13): [PMID:28644035] [10.1021/acs.jmedchem.7b00563]

Source

Source(1):

• Scientific Literature