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Could a invertebrate, for this lets say, a centipede/millipede, evolve into something like that of Pikaia? or something similar? Just an invertebrate turning into something similar or what would look like a vertebrate. Is that even possible in the first place? I was thinking maybe tagmosis could do some of the magic but other than that, I hit rock bottom.

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    $\begingroup$ Define similar. Or consider the hummingbird and the hawk moth: en.wikipedia.org/wiki/Sphingidae $\endgroup$ – jamesqf Jun 24 '20 at 16:30
  • $\begingroup$ Your question is very vague because it covers 100 million years of evolution that happened 500 million years ago, and asks if a centipede can develop many complex features like: bones, endoskeleton, spine,red blood cells, lungs/gills, and lose all the features that define arthropods. best to read up about "earliest vertebrate fossil" and "earliest terrestrial vertebrate" $\endgroup$ – DeltaEnfieldWaid Jun 25 '20 at 1:36
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This is a very complicated question to answer. evolution of that extent might take many millions of years and nobody can say for sure whether something like that would actually happen.

If we look back in time (https://socratic.org/questions/how-did-vertebrates-evolve), organisms with exoskeletons such as ostracoderms appeared before vertebrates. So, perhaps arthropods like centipedes and millipedes could evolve into a vertebrate if it benefits the species in their particular environment.

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    $\begingroup$ Thank you! Mad respect $\endgroup$ – lem0n Jun 25 '20 at 4:29

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