ID: ALA1834932

Max Phase: Preclinical

Molecular Formula: C27H27BrN4O9S

Molecular Weight: 663.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc2cc(C(=O)N3CC(CBr)c4c3cc([N+](=O)[O-])c3cc(S(=O)(=O)NCCO)ccc43)[nH]c2c(OC)c1OC

Standard InChI:  InChI=1S/C27H27BrN4O9S/c1-39-22-9-14-8-19(30-24(14)26(41-3)25(22)40-2)27(34)31-13-15(12-28)23-17-5-4-16(42(37,38)29-6-7-33)10-18(17)20(32(35)36)11-21(23)31/h4-5,8-11,15,29-30,33H,6-7,12-13H2,1-3H3

Standard InChI Key:  MLDRXLUHEDTBSX-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: 663.50

Molecular Weight (Monoisotopic): 662.0682

AlogP: 3.66

#Rotatable Bonds: 10

Polar Surface Area: 173.33

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.96

CX Basic pKa:

CX LogP: 2.09

CX LogD: 2.09

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.13

Np Likeness Score: -0.70

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]

Source

Source(1):

• Scientific Literature