A rant about data quality: machines first, humans second…

Originally posted on Cheminformatics 2.0:

GraphicalAbstractRecently one of my papers emerged through the publication system of Journal of Cheminformatics, entitled “Machines first, humans second: on the importance of algorithmic interpretation of open chemistry data“, co-authored with Antony Williams and Sean Ekins, and incorporated into the JC Bradley Memorial Issue. Spoiler alert: the paper is about how if you’re publishing open lab notebook data without adhering to rigorously defined standards for machine readability, then you’re mostly wasting your time, and arguably making the open data situation even worse than it already is. The tone of the article is a bit less polite than I normally try to be, so fair warning, but it’s all for a good cause.

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How to leave a strong impression

Originally posted on Org Prep Daily:

I got a summer internship in a natural product synthetic group, a quarter century ago when I was in high school. It was a very nice lab, doing medicinal chemistry on cardioglycosides, and I really liked it there. But I didn’t realize that the PI from the group wasn’t thrilled to have me (he was asked to take some random kid as a community outreach initiative, and he could not turn it down.) So, I was promptly sent out of the way, to the library. In those days, the literature search used to be done with printed indexes of Chemical Abstracts. It was like slogging away through a supermarket shelf filled with phone books;  I spent three weeks doing this.

Undeterred, I was nagging the PI to have me try experimental chemistry. Finally, he would let me prepare an acetylated analog of a frog cardanolide, as analytical standard. He instructed…

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Retosiban, GSK221149A

Originally posted on New Drug Approvals:

Retosiban structure.svg

Retosiban, GSK221149A


MW 494.5827, MF C27 H34 N4 O5

Oxytocin antagonist

Threatened pre-term labour


UNII-GIE06H28OX, GSK 221149A,  820957-38-8,



(3R.6R)-3-(2,3-dihvdro-1 H-inden-2-v0-1 -( R)-1 -(2-methyl-1 ,3-oxazol-4- yl)-2-(4-morpholinyl)-2-oxoethyll-6-r(1S -1-methylpropyn-2.5- piperazinedione

2,​5-​Piperazinedione, 3-​(2,​3-​dihydro-​1H-​inden-​2-​yl)​-​1-​[(1R)​-​1-​(2-​methyl-​4-​oxazolyl)​-​2-​(4-​morpholinyl)​-​2-​oxoethyl]​-​6-​[(1S)​-​1-​methylpropyl]​-​, (3R,​6R)​-

Morpholine, 4-[(2R)-[(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-[(1S)-1-methylpropyl]-2,5-dioxo-1-piperazinyl](2-methyl-4-oxazolyl)acetyl]-

Retosiban (GSK-221,149-A)[1][2] is an oral drug which acts as a selective, sub-nanomolar (Ki = 0.65 nM) oxytocin receptorantagonist with >1400-fold selectivity[3] over the related vasopressin receptors and is being developed by GlaxoSmithKline for the treatment of preterm labour.[4][5]

Retosibanis an oxytocin (OT) antagonist in phase III clinical trials at GlaxoSmithKline for the prevention of preterm labor. OT antagonism is widely known to inhibit spontaneous uterine contractions.

Retosiban is a diketopiperazine nonpeptide compound with high potency and selectivity for the OT receptor over vasopressin receptors.

This  candidate has been shown to block oxytocin-induced…

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XMDS: progress toward structure sketcher

Originally posted on Cheminformatics 2.0:

xmds_sk01Since the last sneak preview, the skunkworks project “XMDS” – the Mac OS X desktop version of the Mobile Molecular DataSheet app – has gained enough functionality to make another screenshot, this time showing what the actual molecular drawing interface might look like once it’s done.

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Originally posted on New Drug Approvals:



Molecular Formula: C18H20FN3O4; (Formula Weight: 361.37;

mp: 270-275°C;

Ofloxacin is one kind of white or almost powder or off-white solid.

The Systematic (IUPAC) name of this chemical is (RS)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid


Apazix; Bactocin; Exocin; Flobacin; Floxal; Floxil; Floxin; Girasid; Monoflocet; Ocuflox; Oflocet; Oflocin; Oxaldin; Tarivid; Urosin; Visiren; Zanocin

DL-8280; HOE-280; Ofloxacinum


OFLOXACIN was developed as a broader-spectrum analog of norfloxacin, the first fluoroquinolone antibiotic, Ofloxacin was first patented in 1982 (European Patent Daiichi) and received U.S. Food and Drug Administration (FDA) approval December 28, 1990. In the United States name branded ofloxacin is rarely used anymore, having been discontinued by the manufacturer (Ortho McNeil Janssen). Johnson and Johnson’s annual sales of Floxin in 2003 was approximately $30 million, where as their combined sales of Levaquin/Floxin exceeded $ 1.15 billion in the same year. During the 2008 Johnson & Johnson shareholder’s meetings, the…

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CS 3150, angiotensin II receptor antagonist, for the treatment or prevention of such hypertension and heart disease

Originally posted on New Drug Approvals:

CS-3150,  (XL550)

CS 3150, angiotensin II receptor antagonist,  for the treatment or prevention of such hypertension and heart disease similar to olmesartan , losartan, candesartan , valsartan,  irbesartan,  telmisartan, eprosartan,

 Cas name 1H-​Pyrrole-​3-​carboxamide, 1-​(2-​hydroxyethyl)​-​4-​methyl-​N-​[4-​(methylsulfonyl)​phenyl]​-​5-​[2-​(trifluoromethyl)​phenyl]​-​, (5S)​-

CAS 1632006-28-0 for S conf

MF C22 H21 F3 N2 O4 S

MW 466.47


CAS 1632006-28-0 for S configuration

1- (2-hydroxyethyl) -4-methyl -N- [4- (methylsulfonyl) phenyl] -5- [2- (trifluoromethyl) phenyl] -1H- pyrrole-3-carboxamide

(S) -1- (2- hydroxyethyl) -4-methyl -N- [4- (methylsulfonyl) phenyl] -5- [2- (trifluoromethyl) phenyl] -1H- pyrrole-3-carboxamide

(+/-)-1-(2-hydroxyethyl)-4-methyl-N-[4-(methylsulfonyl)phenyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxamide, CAS 880780-76-7



WO 2014168103

WO 2008126831

WO2008 / 126831 (US Publication US2010-0093826)http://www.google.co.in/patents/EP2133330A1?cl=en

WO 2015012205

WO 2006012642..compound A;..http://www.google.com/patents/WO2006012642A2?cl=en

WO2006 / 012642 (US Publication US2008-0234270)

WO 2015030010…http://www.google.com/patents/WO2015030010A1?cl=en

JAPAN PHASE 2……….Phase 2…

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