search

ebi-chebi / ChEBI

Chemical Entities of Biological Interest (ChEBI) is a freely available dictionary of molecular entities focused on ‘small’ chemical compounds.
https://www.ebi.ac.uk/chebi
Creative Commons Attribution 4.0 International
42 stars 10 forks source link

Enantiomers of hexahelicene #4427

Open K-r-ll opened 1 year ago

K-r-ll commented 1 year ago

Please create two enantiomers of hexahelicene (CHEBI:33150) so that

(P)-hexahelicene is a hexahelicene (CHEBI:33150) (M)-hexahelicene is a hexahelicene (CHEBI:33150) (P)-hexahelicene is enantiomer of (M)-hexahelicene

References: IUPAC Blue Book P-92.1.2.2.1

PubMed references: PMID: 29313040 PMID: 29722420 PMID: 30681334 PMID: 32587284

//

Please find attached the 2-D and 3-D diagrams. The 3-D diagrams are just for illustration purposes, they are obtained by optimisation of 2-Ds with Jmol and are not exactly accurate. The supplementary info for PMID: 29313040 contains a number of DFT-optimised 3-D models

(P)-hexahelicene-2D Ketcher 09042313192D 1 1.00000 0.00000 0

26 31 0 0 0 999 V2000 1.0396 -0.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9389 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1404 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1404 -2.1385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0397 -2.6577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9389 -2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -0.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6580 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6581 -2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -2.6578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 0.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6580 0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5573 0.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5572 -0.5810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4402 1.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4647 1.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8381 -0.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8381 0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9388 0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9389 2.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 2.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1593 1.1494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6581 2.0147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1840 1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 2.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 3 4 2 0 0 0 4 5 1 0 0 0 5 6 2 0 0 0 6 2 1 0 0 0 3 7 1 0 0 0 7 8 2 0 0 0 8 9 1 0 0 0 9 10 2 0 0 0 10 4 1 0 0 0 7 11 1 0 0 0 11 12 2 0 0 0 12 13 1 0 0 0 13 14 2 0 0 0 14 8 1 0 0 0 15 16 2 0 0 0 1 2 2 0 0 0 2 17 1 0 0 0 17 18 2 0 0 0 18 19 1 0 0 0 19 20 2 0 0 0 20 1 1 0 0 0 19 21 1 0 0 0 21 22 2 0 0 0 22 16 1 1 0 0 20 15 1 1 0 0 11 23 1 6 0 0 12 24 1 0 0 0 23 25 2 0 0 0 24 26 2 0 0 0 26 25 1 6 0 0 M END

//

(P)-hexahelicene-3D __Jmol-14_09042313533D 1 1.00000 0.00000 0 Jmol version 14.6.4_2016.10.26 2016-10-26 12:26 EXTRACT: ({0:41}) 42 47 0 0 0 0 1 V2000 3.46103 5.42413 0.07520 C 0 0 0 0 0 0 3.26953 6.79978 0.46361 C 0 0 0 0 0 0 2.25677 4.55582 0.02700 C 0 0 0 0 0 0 0.99980 5.27349 0.03164 C 0 0 0 0 0 0 0.89877 6.63840 0.26990 C 0 0 0 0 0 0 2.00944 7.37752 0.54245 C 0 0 0 0 0 0 2.11505 3.07301 -0.02713 C 0 0 0 0 0 0 0.82958 2.54186 -0.41168 C 0 0 0 0 0 0 -0.30902 3.33224 -0.47948 C 0 0 0 0 0 0 -0.22521 4.66616 -0.20161 C 0 0 0 0 0 0 3.08496 2.04247 0.31039 C 0 0 0 0 0 0 2.86142 0.68721 -0.09320 C 0 0 0 0 0 0 1.64426 0.29266 -0.63204 C 0 0 0 0 0 0 0.61230 1.19899 -0.72092 C 0 0 0 0 0 0 5.22312 4.00424 -1.05513 C 0 0 0 0 0 0 6.56405 3.66074 -1.24550 C 0 0 0 0 0 0 4.32048 7.66150 0.76469 C 0 0 0 0 0 0 5.62355 7.22866 0.66658 C 0 0 0 0 0 0 5.89505 5.97872 0.12632 C 0 0 0 0 0 0 4.83680 5.10572 -0.27165 C 0 0 0 0 0 0 7.24498 5.62312 -0.05696 C 0 0 0 0 0 0 7.57272 4.44864 -0.71246 C 0 0 0 0 0 0 4.23436 2.25743 1.08989 C 0 0 0 0 0 0 3.84949 -0.30048 0.08442 C 0 0 0 0 0 0 5.20599 1.27002 1.27451 C 0 0 0 0 0 0 5.03062 0.00346 0.73809 C 0 0 0 0 0 0 -0.06459 7.14637 0.28304 H 0 0 0 0 0 0 1.88109 8.43234 0.77895 H 0 0 0 0 0 0 -1.28295 2.91304 -0.70778 H 0 0 0 0 0 0 -1.15297 5.23681 -0.20689 H 0 0 0 0 0 0 1.45760 -0.73913 -0.91026 H 0 0 0 0 0 0 -0.35846 0.83680 -1.04378 H 0 0 0 0 0 0 4.47729 3.37253 -1.52716 H 0 0 0 0 0 0 6.81392 2.76915 -1.80515 H 0 0 0 0 0 0 4.14576 8.68203 1.08995 H 0 0 0 0 0 0 6.42128 7.91078 0.93967 H 0 0 0 0 0 0 8.04484 6.26811 0.29122 H 0 0 0 0 0 0 8.61712 4.17042 -0.84790 H 0 0 0 0 0 0 4.40783 3.21817 1.56408 H 0 0 0 0 0 0 3.69357 -1.31502 -0.26722 H 0 0 0 0 0 0 6.10427 1.49964 1.83225 H 0 0 0 0 0 0 5.79647 -0.76011 0.86969 H 0 0 0 0 0 0 1 3 1 0 0 0 3 4 2 0 0 0 4 5 1 0 0 0 5 6 2 0 0 0 6 2 1 0 0 0 3 7 1 0 0 0 7 8 2 0 0 0 8 9 1 0 0 0 9 10 2 0 0 0 10 4 1 0 0 0 7 11 1 0 0 0 11 12 2 0 0 0 12 13 1 0 0 0 13 14 2 0 0 0 14 8 1 0 0 0 15 16 2 0 0 0 1 2 2 0 0 0 2 17 1 0 0 0 17 18 2 0 0 0 18 19 1 0 0 0 19 20 2 0 0 0 20 1 1 0 0 0 19 21 1 0 0 0 21 22 2 0 0 0 22 16 1 0 0 0 20 15 1 0 0 0 11 23 1 0 0 0 12 24 1 0 0 0 23 25 2 0 0 0 24 26 2 0 0 0 26 25 1 0 0 0 27 5 1 0 0 0 28 6 1 0 0 0 29 9 1 0 0 0 30 10 1 0 0 0 31 13 1 0 0 0 32 14 1 0 0 0 33 15 1 0 0 0 34 16 1 0 0 0 35 17 1 0 0 0 36 18 1 0 0 0 37 21 1 0 0 0 38 22 1 0 0 0 39 23 1 0 0 0 40 24 1 0 0 0 41 25 1 0 0 0 42 26 1 0 0 0 M END

//

(M)-hexahelicene-2D Ketcher 09042313252D 1 1.00000 0.00000 0

26 31 0 0 0 999 V2000 1.0396 -0.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9389 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1404 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1404 -2.1385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0397 -2.6577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9389 -2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -0.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6580 -1.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6581 -2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -2.6578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 0.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6580 0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5573 0.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5572 -0.5810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4402 1.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4647 1.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8381 -0.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8381 0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9388 0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9389 2.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 2.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1593 1.1494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6581 2.0147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1840 1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 2.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 3 4 2 0 0 0 4 5 1 0 0 0 5 6 2 0 0 0 6 2 1 0 0 0 3 7 1 0 0 0 7 8 2 0 0 0 8 9 1 0 0 0 9 10 2 0 0 0 10 4 1 0 0 0 7 11 1 0 0 0 11 12 2 0 0 0 12 13 1 0 0 0 13 14 2 0 0 0 14 8 1 0 0 0 15 16 2 0 0 0 1 2 2 0 0 0 2 17 1 0 0 0 17 18 2 0 0 0 18 19 1 0 0 0 19 20 2 0 0 0 20 1 1 0 0 0 19 21 1 0 0 0 21 22 2 0 0 0 22 16 1 6 0 0 20 15 1 6 0 0 11 23 1 1 0 0 12 24 1 0 0 0 23 25 2 0 0 0 24 26 2 0 0 0 26 25 1 1 0 0 M END //

(M)-hexahelicene-3D __Jmol-14_09042313533D 1 1.00000 0.00000 0 Jmol version 14.6.4_2016.10.26 2016-10-26 12:26 EXTRACT: ({0:41}) 42 47 0 0 0 0 1 V2000 3.59192 2.21813 -0.03284 C 0 0 0 0 0 0 3.78342 0.84248 -0.42124 C 0 0 0 0 0 0 4.79618 3.08644 0.01536 C 0 0 0 0 0 0 6.05315 2.36877 0.01072 C 0 0 0 0 0 0 6.15418 1.00386 -0.22754 C 0 0 0 0 0 0 5.04351 0.26474 -0.50008 C 0 0 0 0 0 0 4.93790 4.56924 0.06950 C 0 0 0 0 0 0 6.22337 5.10040 0.45405 C 0 0 0 0 0 0 7.36197 4.31002 0.52184 C 0 0 0 0 0 0 7.27816 2.97610 0.24398 C 0 0 0 0 0 0 3.96799 5.59979 -0.26803 C 0 0 0 0 0 0 4.19153 6.95505 0.13557 C 0 0 0 0 0 0 5.40869 7.34960 0.67440 C 0 0 0 0 0 0 6.44065 6.44327 0.76329 C 0 0 0 0 0 0 1.82983 3.63802 1.09749 C 0 0 0 0 0 0 0.48890 3.98152 1.28786 C 0 0 0 0 0 0 2.73247 -0.01924 -0.72233 C 0 0 0 0 0 0 1.42940 0.41360 -0.62421 C 0 0 0 0 0 0 1.15790 1.66354 -0.08395 C 0 0 0 0 0 0 2.21615 2.53654 0.31401 C 0 0 0 0 0 0 -0.19203 2.01913 0.09932 C 0 0 0 0 0 0 -0.51977 3.19362 0.75483 C 0 0 0 0 0 0 2.81859 5.38483 -1.04753 C 0 0 0 0 0 0 3.20346 7.94274 -0.04206 C 0 0 0 0 0 0 1.84696 6.37224 -1.23215 C 0 0 0 0 0 0 2.02233 7.63880 -0.69572 C 0 0 0 0 0 0 7.11754 0.49589 -0.24068 H 0 0 0 0 0 0 5.17186 -0.79008 -0.73658 H 0 0 0 0 0 0 8.33590 4.72922 0.75014 H 0 0 0 0 0 0 8.20592 2.40545 0.24925 H 0 0 0 0 0 0 5.59535 8.38139 0.95262 H 0 0 0 0 0 0 7.41141 6.80546 1.08614 H 0 0 0 0 0 0 2.57566 4.26973 1.56952 H 0 0 0 0 0 0 0.23903 4.87311 1.84751 H 0 0 0 0 0 0 2.90719 -1.03978 -1.04758 H 0 0 0 0 0 0 0.63167 -0.26852 -0.89730 H 0 0 0 0 0 0 -0.99189 1.37415 -0.24886 H 0 0 0 0 0 0 -1.56417 3.47184 0.89026 H 0 0 0 0 0 0 2.64512 4.42409 -1.52172 H 0 0 0 0 0 0 3.35938 8.95728 0.30958 H 0 0 0 0 0 0 0.94868 6.14262 -1.78988 H 0 0 0 0 0 0 1.25648 8.40237 -0.82733 H 0 0 0 0 0 0 1 3 1 0 0 0 3 4 2 0 0 0 4 5 1 0 0 0 5 6 2 0 0 0 6 2 1 0 0 0 3 7 1 0 0 0 7 8 2 0 0 0 8 9 1 0 0 0 9 10 2 0 0 0 10 4 1 0 0 0 7 11 1 0 0 0 11 12 2 0 0 0 12 13 1 0 0 0 13 14 2 0 0 0 14 8 1 0 0 0 15 16 2 0 0 0 1 2 2 0 0 0 2 17 1 0 0 0 17 18 2 0 0 0 18 19 1 0 0 0 19 20 2 0 0 0 20 1 1 0 0 0 19 21 1 0 0 0 21 22 2 0 0 0 22 16 1 0 0 0 20 15 1 0 0 0 11 23 1 0 0 0 12 24 1 0 0 0 23 25 2 0 0 0 24 26 2 0 0 0 26 25 1 0 0 0 27 5 1 0 0 0 28 6 1 0 0 0 29 9 1 0 0 0 30 10 1 0 0 0 31 13 1 0 0 0 32 14 1 0 0 0 33 15 1 0 0 0 34 16 1 0 0 0 35 17 1 0 0 0 36 18 1 0 0 0 37 21 1 0 0 0 38 22 1 0 0 0 39 23 1 0 0 0 40 24 1 0 0 0 41 25 1 0 0 0 42 26 1 0 0 0 M END

K-r-ll commented 1 year ago

More PubMed references:

PMID: 17744402 PMID: 37024717 PMID: 31022934 PMID: 29313040 PMID: 36707940