Thursday, November 9, 2023

A Dictionary of Comparative Organic Chemistry - vitamins, hormones, neurotransmitters, medicines, polymers, and poisons

Here is a list of about 120 organic compounds arranged according to their composition. I chose the number 120 because the periodic table currently lists 118 elements. And also because I got tired of copying and pasting. Most of the entries are medicines from the WHO list of essential medicines. 

The beauty of the periodic table is that it allowed chemists to predict the existence and properties of elements before they were discovered. This is because the closer elements are on the table, the more alike they are. In the same way, if we compare similar organic compounds, we can predict the existence of compounds that haven't been discovered or synthesized yet. Those chemicals could have useful properties or be cheaper to synthesize than existing ones with the same use. 

Comparative anatomy and linguistics are well-established fields with proven results. It is time to take a similar approach to chemistry. 

In my method, the number of carbon atoms acts like the atomic number of an element. The element groups act like groups and periods. 

For example, we can see that there is a big gap between aflatoxin and ivermectin in the CHO group. Within that gap are a bunch of vitamins and hormones. Could there be useful medicines yet to be discovered lurking in that gap? Probably. After penicillin was discovered, there was a race to collect species of fungi to see if more antibiotics could be found. 

Antibiotic resistance is a serious problem, and of course, there's plenty of money to be made in discovering a new one. Based on the table below, there ought to be more research into organic compounds containing sulfur and phosphorus. 

To give another example of how to use the table, we see that streptomycin with 21 carbon atoms fits in perfectly between quinine (20 carbon atoms) and doxycycline (22 carbon atoms). This implies there are similar molecules in the CHNO family with antibacterial or antimalarial properties.  

Ideally, I'd fill out this list with a few thousand chemicals and run it through a neural net to train it to identify medicines. I am currently work on an NSF Seed Fund grant proposal for that. If you would like to help with that, please leave a comment or email me at: harty.thomas@gmail.com

It would be great to organize the Beilstein database like this but would take forever unless there some way to write a computer to organize the electronic version. The current database has millions of entries.

As a future step, I'd like to repeat this method for proteins. That is, ordering them by amino acids. I know the key to understanding proteins is their 3D shape, but to keep things simple, I'd start by just organizing them by which amino acids they contained. 

Science marches on. Feel free to enjoy this relevant musical interlude (chemistry starts at 1:10 mark):


I watched the above for the first time when I was about 5 and it's been stuck in my mind ever since. 


CN, CNX = poisons, antidotes, coolants

CH, CHX = aromatic compounds, pesticides

CHN, CHNX = stimulants, depressants

CHO, CHOX = fat soluble vitamins, hormones, artificial flavors, fuel additives

CHNO = water soluble vitamins, neurotransmitters, amino acids, opioids, painkillers, pesticides, psychoactive drugs, antidotes

CHNOX  = other water soluble vitamins, other amino acids, other hormones, pesticides, nerve gas, antibiotics


CX, CN, CNX


Prussian blue    C₁₈Fe₇N₁₈

hydrogen cyanide HCN

teflon           (C2F2)n

freon            CCl₂F₂

PVC              (C2H3Cl)n

phosgene         COCl₂


CH, CHX


benzene         C₆H₆

DDT             C₁₄H₉Cl₅

dichlorobenzene C₆H₄Cl₂

styrene         C₈H₈


CHO, CHOX


aspirin         C₉H₈O₄

ethanol         C₂H₆O

ibuprofen       C₁₃H₁₈O₂

vitamin A       C₂₀H₃₀O

vitamin B8      C₆H₁₂O₆

vitamin C       C₆H₈O₆

vitamin D       C₂₈H₄₄O

vitamin E       C₂₉H₅₀O₂

vitamin K       C₃₁H₄₆O₂

prostacyclin    C₂₀H₃₂O₅

aldosterone     C₂₁H₂₈O₅

testosterone    C₁₉H₂₈O₂

estrogen        C₁₈H₂₄O₂

progesterone    C₂₁H₃₀O₂

cortisol        C₂₁H₃₀O₅

vanillin        C₈H₈O₃

isoamyl acetate C₇H₁₄O₂

prednisolone    C₂₁H₂₈O₅

sarin           C₄H₁₀FO₂P

ivermectin      C48H74O14

aflatoxin       C17H12O6

formic acid     CH₂O₂

MTBE            C₅H₁₂O

polyester       (C10H8O4)n

permethrin      C21H20Cl2O3


CHN, CHNX


amphetamine     C₉H₁₃N

histamine       C₅H₉N₃

midazolam       C₁₈H₁₃ClFN₃

tear gas        C10H5ClN2

hydralazine     C₈H₈N₄


CHNO 


vitamin B2       C₁₇H₂₀N₄O₆

vitamin B3       C₆H₅NO₂

vitamin B5       C₉H₁₇NO₅

vitamin B6       C₈H₁₁NO₃

vitamin B9       C₁₉H₁₉N₇O₆

choline          [(CH₃)₃NCH₂CH₂OH]+

dopamine         C₈H₁₁NO₂

serotonin        C₁₀H₁₂N₂O

epinephrine      C₉H₁₃NO₃               

acetylcholine    C₇H₁₆NO₂      

glutamic acid    C₅H₉NO₄

GABA             C₄H₉NO₂

norepinephrine    C₈H₁₁NO₃

glycine          C₂H₅NO₂

melatonin        C₁₃H₁₆N₂O₂

histidine        C₆H₉N₃O₂

isoleucine       C₆H₁₃NO₂

leucine          C₆H₁₃NO₂

lysine           C₆H₁₄N₂O₂ 

phenylalanine    C₉H₁₁NO₂     

threonine        C₄H₉NO₃

tryptophan       C₁₁H₁₂N₂O₂

valine           C₅H₁₁NO₂

cocaine          C₁₇H₂₁NO₄

morphine         C₁₇H₁₉NO₃

heroin           C₂₁H₂₃NO₅

fentanyl         C₂₂H₂₈N₂O

acetaminophen    C₈H₉NO₂

codeine          C₁₈H₂₁NO₃

LSD              C₂₀H₂₅N₃O

auxin            C₁₀H₉NO₂

lidocaine        C₁₄H₂₂N₂O

atropine         C17H23NO3

scopolamine      C₁₇H₂₁NO₄

caffeine         C₈H₁₀N₄O₂

ondansetron       C18H19N3O

naloxone         C₁₉H₂₁NO₄

quinine          C₂₀H₂₄N₂O₂

phenobarbital    C₁₂H₁₂N₂O₃

tetrodotoxin     C₁₁H₁₇N₃O₈

doxycycline      C₂₂H₂₄N₂O₈

azithromycin     C₃₈H₇₂N₂O₁₂

ethambutol       C₁₀H₂₄N₂O₂

streptomycin     C₂₁H₃₉N₇O₁₂

acyclovir        C₈H₁₁N₅O₃

ribavirin        C₈H₁₂N₄O₅

metronidazole    C₆H₉N₃O₃

polyacrylamide   (C₃H₅NO)n

nylon            (C6H11NO)n

bisoprolol       C₁₈H₃₁NO₄

verapamil       C₂₇H₃₈N₂O₄

digoxin          C₄₁H₆₄O₁₄

urea             CO(NH₂)₂


CHNOX


vitamin B1       C₁₂H₁₇N₄OS+

vitamin B7       C₁₀H₁₆N₂O₃S

vitamin B12      C₆₃H₈₈CoN₁₄O₁₄P

methionine       C₅H₁₁NO₂S

oxytocin         C₄₃H₆₆N₁₂O₁₂S₂

diazepam         C₁₆H₁₃ClN₂O

fluoxetine       C₁₇H₁₈F₃NO

metoclopramide   C₁₄H₂₂ClN₃O₂

ketamine         C13H16ClNO

triiodothyronine C₁₅H₁₂I₃NO₄

glyphosate       C₃H₈NO₅P

VX               C₁₁H₂₆NO₂PS

cladribine       C10H12ClN5O3

albendazole      C₁₂H₁₅N₃O₂S

amoxicillin      C₁₆H₁₉N₃O₅S

ampicillin       C₁₆H₁₉N₃O₄S

penicillin       C₁₆H₁₈N₂O₄S

chloramphenicol  C₁₁H₁₂Cl₂N₂O₅

ciprofloxacin    C₁₇H₁₈FN₃O₃

sildenafil       C22H30N6O4S

clotrimazole     C₂₂H₁₇ClN₂

ritonavir        C₃₇H₄₈N₆O₅S₂

keratin          C2H2BrClO2

mefloquine       C17H16F6N2O

tioguanine       C₅H₅N₅S

chlorhexidine    C₂₂H₃₀Cl₂N₁₀

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